Skip links

Session 240: Some Final Thoughts On Insecure

The Therapy for Black Girls Podcast is a weekly conversation with Dr. Joy Harden Bradford, a licensed Psychologist in Atlanta, Georgia, about all things mental health, personal development, and all the small decisions we can make to become the best possible versions of ourselves.

We made it y’all. This week we wrapped up the fifth and final season of HBO’s Insecure and boy did they wrap it up! So of course Dr. Donna Oriowo is back with us this week to chat all about it. She and I chatted about how each character’s storyline was wrapped up, our personal takeaways from the journey that has been Insecure, and our thoughts on what it might inspire in your life. This episode does contain spoilers.

Where to Find Dr. Oriowo

Grab a copy of Cocoa Butter & Hair Grease

Register for Dr. Oriowo’s Goal Setting Workshop

Instagram: @annodright

Twitter: @drdonnaoriowo

Check out a playlist of all the Insecure related episodes here.

Stay Connected

Is there a topic you’d like covered on the podcast? Submit it at

If you’re looking for a therapist in your area, check out the directory at

Take the info from the podcast to the next level by joining us in the Therapy for Black Girls Sister Circle

Grab your copy of our guided affirmation and other TBG Merch at

The hashtag for the podcast is #TBGinSession.

Make sure to follow us on social media:

Twitter: @therapy4bgirls

Instagram: @therapyforblackgirls

Facebook: @therapyforblackgirls

Our Production Team

Executive Producers: Dennison Bradford & Maya Cole Howard

Producers: Fredia Lucas & Cindy Okereke

Assistant Producer: Ellice Ellis

Read Full Transcript

Session 240: Some Final Thoughts on Insecure

Dr. Joy: Hey, y'all! Thanks so much for joining me for Session 240 of the Therapy for Black Girls podcast. We'll get right into the episode after a word from our sponsors.


Dr. Joy: Well, we've made it! This week, we wrapped up the fifth and final season of HBO’s Insecure, and boy did they wrap it up! So of course, Dr. Oriowo is back with us this week to chat all about it. If you've missed her here before, she's an author, international speaker and certified sex and relationship therapist in the Washington DC Metro area. She's the owner of AnnodRight and specializes in working with black women on issues related to colorism and texturism and its impacts on mental and sexual health. She's also the author of Cocoa Butter & Hair Grease: A Self Love Journey Through Hair and Skin.

Dr. Oriowo and I chatted about how each character’s storyline was wrapped up, our personal takeaways from the journey that has been Insecure, and our thoughts on what it might inspire in your own life. This episode does contain spoilers. As always, we love hearing your thoughts about the show. Shout out to Dr. Michelle Patrice and @TheMaroonV on Twitter and @JustSharing on Instagram for letting us know you were anxiously awaiting the recap this week, you knew it was coming. Thank y'all so much for listening. And let us know your thoughts about the finale. Make sure to use the hashtag #TBGinSession on social media so that we can join the conversation. Here is our conversation.

Dr. Joy: We have finally come to the series finale of Insecure... I feel like we sang it prematurely a couple of weeks ago because now it really is the end and it feels so, so sad.

Dr. Oriowo: I'm in a happy sad place. I'm also excited to see what Issa Rae will do moving forward.

Dr. Joy: Before we jump too far into all of what has unfolded in the past like 24 hours... not even 24 hours because we are recording the morning after. Insecure originally premiered on October 9, 2016, which I had not remembered. That's the day before my birthday and so I didn't remember Insecure pairing that closely to my birthday but it feels very celebratory now that I go back and know that.

Dr. Oriowo: Yeah, it is very fitting.

Dr. Joy: Very fitting, right. October 2016, and so if you think about like where your life was and what was going on then, what was happening for you in October 2016? Do you remember?

Dr. Oriowo: 2016, that year I graduated with my PhD. I started AnnodRight that same year, I started it in June, as a matter of fact. I'm just wow. I mean 2016, it was both a minute ago and not that long ago all at the same time because I’m just like, oh, I bought my house in 2016. I did a lot of things in 2016.
Dr. Joy: That is so cool. I had been married for, what, almost four years at that point and then I had a three-year-old and an almost six-month-old at that point. And so, you know, just even thinking about like the trajectory your life has taken since the beginning of Insecure, it feels like a really cool way to kind of mark this time period in your life. Because I think for both of us there has been just like tremendous personal and professional growth in the same time we have watched Insecure start and finish.

Dr. Oriowo: True. In 2016, I didn't even know you.

Dr. Joy: I know, right? It just feels like wow, like so much was happening and Insecure in very weird and beautiful ways brought so many things together.

Dr. Oriowo: Absolutely. And it's funny because it's like looking at the trajectory of the characters of where Issa started working for We Got Y’all to working for herself, I was looking like that's my trajectory. I went from working for somebody to not working for nobody but me. And I'm just like oh, wow, look at that, through the years how much change and growth can actually happen. But also it has me thinking about how much change and growth we often dismiss because we don't take reflective moments like this.

Dr. Joy: Such a good point. It feels very fitting that we are also wrapping up 2021 and heading into 2022 and that is I think the time when a lot of people are reflective like, oh, let me kind of do some reflection over the year. But it would be good, I think, to take those pauses more often. You know, I have been feeling very reflective just about the trajectory of Insecure with the podcast. I was trying to think, like when did we even come up with the idea to start doing the recap so regularly?

You have been on the podcast several times, related to Insecure and unrelated to Insecure, but the first time we started doing the recaps was with the Season 4 premiere which premiered in April 2020. And so I know for me, that was like the height of the pandemic and so in a lot of ways it felt like Insecure gave us a break. It gave us something like joyful and fun to kind of focus on with the backdrop of the pandemic kind of unfolding. And you know, to me, it is not surprising that we did it really starting with Season 4, because of course Season 4 was all about Issa and Molly's relationship more heavily.

And just kind of given both of our focus, and I'm deep into writing about sisterhood right now, it feels very fitting that that was where there was a lot of energy–let's talk about the breakdown and what's happening in this sisterhood. Because I think a lot of people just really, really related to that and that was something that I don't think we had seen fleshed out so beautifully on any other show. Just the love between sisters, like what happens when a friendship is not going so well and how do we get it back on the tracks? And how does this even happen? And the fallout that can happen. Again, I think we see lots of depictions of like romantic breakups and family stuff, but we don't often see what happens when you fall out with your girl and how that can really turn your world upside down.

Dr. Oriowo: Yeah, how do you get back on track? Yeah. And it's funny because it had me thinking about these other shows that I've watched, particularly Grey's Anatomy, and how the real love story for me was never about Meredith and Derek, it was always Christina and Meredith. And the same thing here. It's like, yeah, there's this focus on whether or not Issa’s gonna be with Lawrence or Nathan or all that stuff. All that was always ancillary. The relationship was always Molly and Issa. It was always about them and I think that we got caught up in a lot of ways in the world outside of them. And with Season 4 being the culmination of, okay, it’s definitely gone awry, I feel like that helped us to refocus as well. And I think that we needed to refocus.

Dr. Joy: Well, well, listen. How were you feeling leading up to the actual premiere of the finale last night?

Dr. Oriowo: You know, it was surreal because in my mind it was not... It just wasn't. It's just like it was not the finale for me. I was just like, nope, we’re not done.

Dr. Joy: You were in a bit of a denial.

Dr. Oriowo: In my mind, it was we're not done so I was like, oh, I'm looking forward to Sunday next. And I'm like, oh well, I guess it hasn't hit me yet that it's over. Like I'm not gonna be staying up, because you know I had to stay up...

Dr. Joy: Right. You know I frequently have to text you like hey girl, listen, don’t go to sleep before Insecure comes on.

Dr. Oriowo: Because you know I'd be in the bed and completely forget and be like, oh damn, I forgot. But like it's weird because I'm just like, no, it's not over but it's over.

Dr. Joy: But it's over, it’s over, sis. Yeah, I think that the characters have felt so real. I think people have these kinds of like relationships with their favorite shows but I feel like Insecure created a world that made the characters feel so real that we felt very connected to, like oh, let's catch up and see what's happening with them on Sunday night. And so to not have that I think is a very surreal kind of weird experience. I found myself kind of teary on and off yesterday. I was like, girl, what is going on?

Dr. Oriowo: That part hit me today when I rewatched it. I was just like, oh, okay. Because I got through the entire episode, not a tear in eye. Because today is the day that I was like, oh, it's not coming back, the show is over. And I was having all the emotions suddenly all at once.

Dr. Joy: Yeah, and I think it may be important to kind of talk a little bit more about that because in June when they were shooting the finale, I remember them doing a lot of sharing on social, around saying goodbye to one another. And I thought that that was so impressive and so important because I don't think that we typically see that. Like we don't typically see the effort of saying goodbye to a thing or a person. And so it felt very cool that they were like sharing that. Well, one, that they were doing it with one another, but also sharing it with us. And now I know that a lot of that was also because they were like making a documentary out of the final season, about what it was like to wrap up the show.

But I think it is important around like just saying goodbyes. We've talked about that on the podcast before, like how we just don't have a lot of practice saying goodbyes and we would typically like to just rush past them because it's uncomfortable. It's uncomfortable, it brings up a lot of feelings that we don't quite know what to do with. And so I feel like this, in some ways, is really giving people an opportunity to formally say goodbye to a thing, where they may not typically choose to go that route.

Dr. Oriowo: Yeah. We don't have the practice and it's almost like we make it seem as though it’s sort of unimportant. Like we're all about the move forward, move forward, move forward. But we forget that in moving forward and in making choices, you say yes to something and say no to something else. And that you get to grieve that you're saying no to this other thing, you get to acknowledge that that thing is changing and it's sad, and you get to be sad. This is a transition point. Yes, you’ve achieved and you're happy and you're moving forward, and you can be sad at the same time so I am both happy and sad that Insecure is over. I'm happy in that we loved it for what it was, for what it gave, for how we felt, how it felt connected to us. And we get to grieve that because we love it, and that's okay.

Dr. Joy: Yeah, and I want people not to feel like it's silly to be sad. Just because they are fictional characters, doesn't mean that it didn't spark something very real for you or that it made you think about things or brought you joy or whatever you may have needed in that moment. So, you know, if you're feeling kind of like, oh, gosh, why am I sad or whatever, it's because there was something real that was created by Issa and the team kind of giving this to us every week. There's nothing to be ashamed about if you're feeling a little bit sad or grieving the ending of something that may have been important to you.

Dr. Oriowo: Yeah.

Dr. Joy: The title of the finale was “Everything Gonna Be, Okay?!” I feel like that has multiple different meanings. Everything gonna be, like it is what it is, like life will life, despite our attempts to control. But also, everything will be okay, like in the end it will all be okay. What were your thoughts about the title?

Dr. Oriowo: I felt like the title was very fitting and I was feeling that, that everything will be. It will be. Everything is, you know, it is what it is. And the okay part, I think that, okay, it ends up being up to you. And I feel like that's what we got in, what was it, like the second anniversary of things, so like the second birthday, after Molly’s second birthday.

Dr. Joy: The second round of birthdays.

Dr. Oriowo: Yes. When Issa was in the office space and Lawrence came through and it was just like I had to believe that it would work for it to work. And I'm just like, oh okay, so it'll be okay, okay? For me, this speaks to that part around like, number one, they're no longer really insecure. They are secure in themselves. You don't have to be secure in the stuff around you, you just need to be secure in you. Know who you are, know what you're capable of, believe in your abilities. And believe that you are able to grow, that you're able to grow and change, and that you're great as you are and you will continue to do well. And that in your belief in you, yes, there are circumstances that are outside of your control but in the end of the day it's about what you can do. That you do what you can and the rest is up to the people who are interacting with you and to the circumstances of the life that you're in. So yes, things will be okay because you did what you could do. Whether or not other people accept it, see it, praise it, whatever, that's on them. But you do you.

Dr. Joy: Last time we talked, we titled the episode Decisions, Decisions because it felt like Issa had a lot of decisions she was gonna make. Lawrence has now told her I'm still in love with you basically, I don't feel like my life is happy. And Nathan rose up like, hey, what's going on here? And so this episode picked up at that point, we see that he has now driven her home and is kind of feeling like, okay, I just don't think that this is something for me. And so I think I thought we were gonna have more time for her to make a decision between Nathan and Lawrence, when clearly Nathan opted out. Like he was just like, you know what, this is not good for me anymore.

Dr. Oriowo: And that shit is so doggone true. I'm looking like, yes, you get decisions, decisions, but so do other people. And he was just like, well, Issa’s over here trying to make choices and that's good Issa gets to do that, but so does Nathan, and Nathan chose not. And honestly, I love that for him. For him to be like, yo, like... What I interpreted is that he hopped all the way out of his character and that he did not like that for himself and that it did not feel good for himself. And that he realized that he can't do this like this. Like, what do you say, this stuff is toxic to me. And I'm just like, yo. We know that he is nonconfrontational. He tends to keep a lot of things in and let it get to some other head before he say anything about it. And he's just like, look, this doesn't feel good for me, this ain't right for me, and I need to take a step back. That's some real shit and I appreciate that.

Dr. Joy: I do too. But you know, the thing that was concerning for me is that they had just been looking at apartments together so like what was gonna happen...Yeah, what was gonna happen if like that first apartment had been available? And so in the car, we see him saying yeah, for a while this just hasn't quite felt right. And so I'm imagining... again, we only have 30 minutes with these people, but I'm imagining what was happening for him is something that happens for a lot of people. Is that he thought maybe going through the motions would overtake that feeling at some point. Like okay, I'm still feeling a little unsettled but maybe if we move in together, maybe if we do this, then that will go away. When really, we see the underlying feeling was that it just didn't feel like a good fit.

Dr. Oriowo: Yeah. I'm wondering if he was feeling insecure in his relationship with Issa and felt the need to move it forward in those directions. Something feels amiss and I am going to try everything that I can to make it not feel that way, to make myself feel more secure. I need the title. I need you to tell me you love me, I need us to move in, I need us to have a kid, I need us to, I don't know, buy a puppy, whatever it is. And sort of how we like try to drive the relationship forward because we feel insecure and we are trying to do the things that make us feel more connected.

It sort of reminds me like I recently finished this book Come as You Are, and in the book, one of the things is that Emily Nagoski talks about how people talk about sex is so great with a toxic partner. And it's like actually, the sex is so great with the toxic partner because you feel so insecure that this makes you feel more secure so your brain is also latching on to that. It's not even that the sex is great; it's that you feel insecure, so the sex feels great.

Dr. Joy: Right, so in the in the sex is where you feel affirmed.

Dr. Oriowo: Exactly. It's your attachment point. And I think that he was trying to find an attachment point with her. It's one thing to ignore it when it's just y'all two but when the dude that you’ve probably been feeling insecure about is sort of in your face and having a conversation that's not the conversation, and now he's propositioning your girl like you're not in the same party... At that point, it's just like, alright, I can't ignore this anymore. Because, okay, so I wasn't tripping about feeling this way. It wasn't in my head, it was the real deal.

And I think that I wish that more of us felt brave enough to say like, hey, I’ve got this feeling, and talk it out with a partner instead of keeping the thing inside. Because maybe they're feeling it too, maybe they notice it too. Maybe y’all could have a real ass conversation about what it all means. But so many of us are so worried about rocking the boat that the boat sinks.

Dr. Joy: The boat is gone and it sinks.

Dr. Oriowo: It got a big ass hole in the side of the boat. And the hole is there and you knew that there was a hole or you thought there was a hole, but you didn't want to ask them if they thought it was a hole because you didn’t want the boat to sink. Well, it sank anyway.

Dr. Joy: The boat sank anyway, isn’t that something! After she gets out of the car, to me, I feel like I read some sadness in Nathan's face around like Issa not trying to fight when he said like I'm done. Sometimes there will be the like, “no, can we talked about it, da, da, da,” and I think she tried that one time and then after he was resolute in saying I don't think that this is a good idea, she was just like “okay” and walks to her apartment. And I feel like there was some sadness in his face around her not fighting for it or not trying to convince him.

Dr. Oriowo: I thought that was something I was seeing, I’m happy you saw it too.

Dr. Joy: Yeah, I saw it, at least I feel like I saw it. I don't know if that was a part of what they wanted us to see but I definitely feel like I registered some of that on his face.

Dr. Oriowo: Yes. Like oh, wow. Okay, you’re not gonna fight for us so you must really want to be with this other person. Or you must not be sure about me. Even if you're not sure about him, you're definitely not sure about me.

Dr. Joy: Right. Which I think was accurate.

Dr. Oriowo: Yeah.

Dr. Joy: More from my conversation with Dr. Oriowo after the break.


Dr. Joy: We started off back where the last episode picked up and so then we see of course, Issa’s in her home, she thought about everything that had transpired then we see her wake up the next morning and Molly is coming over to check on her. I was like, oh my god, like how are we gonna get to the end? Because now it's feeling like a regular episode and I'm like, oh my god, what's happening here? But then of course, of course, they have it all figured out because that's their job.

We see her having her mirror conversations and her mirror bitch was like super critical, and of course it would be after a night like that. Like your self-talk ramps up after you have some kind of crazy experience like that. But then we see her saying, I just want to fast forward to the part of my life when everything is okay. I thought that that was clever and that it also gives you something to think about, but it was also like the plot device that was gonna throw us into this time travel that we were gonna have.

Dr. Oriowo: Honestly, every time I hear that... I used to think that that was like, oh yeah, why wouldn't you? That's actually the saddest shit that I've ever heard in retrospect. “I just want to fast forward to the part of my life where everything is okay,” to me, as a person who was raised by immigrants (so I’m first gen to this country) it sounds like a very American construct and very sad.

Dr. Joy: Say more about that.

Dr. Oriowo: Like we are so interested in getting to the end of something that we never even enjoy the journey that it takes to get there. I think about like the points in my life where I've been so focused on getting to the end that I didn't enjoy the journey. Like, oh, I just want to get my bachelor's degree. I'm looking like can you be fully present? If you are looking forward so hard, how can you be fully present? You can only be partially present. Because you're really just thinking about the future and what you're going to do with the thing that you get instead of enjoying the journey. Like, yes, you can have the goal, but how do you make sure that you’re present. Enjoy it. Feel the feels of it, the emotional whatever is going to be, just to be in that space and stop being in a rush.

Dr. Joy: I feel like that's what a lot of this was for Issa, especially in this moment. Is that she has had this awful night and it is on the heels of her having these (I think) several weeks and months of not quite feeling like she knew what she wanted to do in her personal life and also her professional life. And so, to me, it makes sense that she would be feeling like I don't want to sit in this sadness and pity anymore, like I really wish I could just fast forward to when my life is together.

Dr. Oriowo: Word. I like some of it in terms of being able to see their lives through these glimpses of celebration. That couple of months skip forward, or however long it was to Molly's birthday. I was actually loving that Molly allowed Issa to throw this party for her, this small gathering, and that Tiffany was able to return and to be present for that and that we got to meet Kelli's boo. And it was a space of allowing people to support and celebrate you.

Dr. Joy: Yeah. After Molly's birthday, then we see Issa’s first birthday party. And so she has a surprise birthday party and we see the gang kind of reassembled. Tiffany was not there for Issa’s surprise birthday party but we do see the reappearance of Nathan now at this surprise party. And so again, we don't know how much time has passed since that night. To me, it felt like it had been a significant amount of time.

Dr. Oriowo: Yes, significant enough to be like, dude, you ain’t communicated with me at all, but you did show up here.

Dr. Joy: Right, right. Enough time where you're not still in your feelings enough to be like I'm definitely not going to that. But also enough time where there has been like this growth and reflection on thinking about, okay, what actually happened?

Dr. Oriowo: Yeah, I think they must have used your workbook.

Dr. Joy: Shout out to the Questions That Need Answers: After the Breakup workbook.

Dr. Oriowo: That one, because I felt like they answered some questions. Because I'm like it's very cute when everyone's like, oh, I just need to talk to him so I can have some closure. Actually, what you need is the workbook and then you know you don't actually need to have no conversation with nobody in order to get that closure. But I like the way that they were able to sort of come together in that moment and it was just like, people come into your life for a reason and I hope that you don't have any regrets.

And I think that oftentimes, we regret the relationships that we've had with people, especially when they've ended, because we have been taught that a relationship ending is a relationship failure, so we don't know how to see the celebration in it. Because I'm just like, oh, that is amazing that you broke up. It's great that you got that divorce. It don't feel great right now, but here's the great part: you know that that person is not for you in the direction your life is currently taking and you have decided to pivot. What is better than that? What is better than that? You're finished. This thing doesn't fit you, you're finished with it. You're able to let it go in peace and find something that fits you. But no, we are a culture of make that shit fit at all costs and if it don't, something's wrong with you.

And I'm talking about from clothes to people. We will hang on to outfits from seven years ago that ain’t fit for 10, thinking that we're gonna bully our body to be back where it was back then. The same way that we try to bully ourselves into being the people that we were back when for people. I'm looking like allow yourself growth and change, and level up your wardrobe. That's all it is. This is a leveling up. It's like, yes, I am hoping you have no regrets, people come into your life for a reason and they also exit when it's time to go.

Dr. Joy: Mm hmm. Yes, the closure comes from you, not from this magical conversation that you're thinking you're gonna have with your ex. I mean, that happens on Lifetime movies but it does not typically happen in real life.

Dr. Oriowo: Not in real life.

Dr. Joy: I think at Issa’s surprise party is also when we see this like side conversation about when Molly is proposing that Kelli actually join the firm. Like she's had this conversation, they’re really excited about the idea of an estate planning kind of wing of the firm. And so we see, and we kind of talked about this last episode, are we gonna see them go into business together at some point? And so we see that that is the proposal with that idea. The next birthday we have is now Tiffany's birthday and so the gang has all assembled in Denver at her beautiful home. She's giving them a tour.

Dr. Oriowo: “And I hate it here,” you can’t forget that.

Dr. Joy: Oh, my gosh. When she finally felt comfortable enough to be like, y'all look, this ain’t it. I'm not loving this at all.

Dr. Oriowo: I think that people don't see that as being vulnerable, and it is. To be like here's my pretty house and I hate it here. And how her husband was just like, yo, my friends ain’t visited. How she’s just like I ain’t got no friends here. His family was excited for all of five minutes and now we've become mundane. I don’t have connection here, I don't have friends. I don’t have a job here and this is not the life that I envisioned for myself.

Dr. Joy: Right. And so when we fast forward, it's still hard to tell like whether they have moved back to LA. I don't think that that was ever really cleared up, like a part of me felt like they had but I don't know for sure because we didn't really kind of revisit where Tiffany's world was–again, after this birthday scene.

Dr. Oriowo: Yeah, we didn't. And I wished that we did, because it would have been nice to know exactly where they were, especially given the promises that she was making to Kelli about being there for her in her journey.

Dr. Joy: Exactly, exactly. So while they are at Tiffany's home in Denver, we see that Issa and Molly are in the kitchen having a conversation. Molly is finishing up some work and Issa sees a picture of the *[inaudible 0:28:08] I think is what their name was of all of the men and their kids. And she looks like longingly at this picture where Lawrence is pictured and so Molly then feels like, okay, this is the moment to ask this question. Like what would you have said that night if Nathan didn't intervene? And so Issa’s like, you know, I'm not really sure, but I think there's a part of her that kind of knows what she would have said. But then again, I feel like this was part two of Molly's conversation that she had in this last episode around like if you're honest with yourself, you know what you really want to do, and get out of your head and stop worrying about what other people are gonna think about the decision and make the decision that you feel like is best for you.

Dr. Oriowo: Yeah. And I think that she had taken that thing to heart about being a wishy washy.

Dr. Joy: Yes.

Dr. Oriowo: And it was funny because didn't Nathan also call her *[inaudible 0:28:56]?

Dr. Joy: Yep.

Dr. Oriowo: So it was like she is trying so hard to not be that that she's also not listening to what it is that she's saying that she wants.

Dr. Joy: Mm hmm, yeah. And I feel like Molly drops her therapy wisdom on her and is talking about like how when she was in the space of overthinking, which clearly indicates that she no longer feels like she does a lot of overthinking... which, of course is growth, we love to see it. We didn’t see Molly in therapy this season but I think it was alluded to like several times that she was still working with her therapist, or at least still had gotten a lot out of that relationship. Even though we didn't see her physically in the office anymore, we still kind of saw some of that therapy piece kind of playing in the background.

Dr. Oriowo: And I just be wondering like, people be getting it from the friends that are in therapy. I'm looking like do you know how much better it would be if you were the friend in therapy too?

Dr. Joy: Right, can you only imagine? Like this is just second-hand information she’s sharing.

Dr. Oriowo: Word. I'm like get into it. You and your friend got into it, y'all should get into therapy together. I'm looking like there are therapists that will see you. That, yes, you can do friendship-based therapy. Come on, let's go. Get this work. And of course, we end that with the news.

Dr. Joy: Yeah, the news. Molly and Issa talking then Molly’s brother calls and we see she takes the call and she gets this devastating news that it sounds like her mom has passed. And so this is the point at which I started bawling in this episode because I thought there had been so many conversations around death, and then we saw her have the stroke earlier this season but then she recovered, and so I thought we had kind of moved...

Dr. Oriowo: Estate planning and all that.

Dr. Joy: Yes, and I thought we had moved past the idea that somebody was actually going to die this season, even though there had been rumblings. And so I felt like, oh man. Like just knowing friends who have gotten that call and like how it just... You can go from having this regular mundane conversation one minute to like your world completely falling apart. And so I would have liked to spend more time there because I think the death of a friend’s parent also impacts a circle. And I think we see a little bit of that in the future scenes but we didn’t get a proper homegoing for Miss Carol and I really would have liked to see...

Dr. Oriowo: Nada, not even a quick Zoom...

Dr. Joy: Not a Zoom, nothing. We didn’t get no kind of...

Dr. Oriowo: It’s more like we zoomed right past it and started talking to Lawrence. I’m looking like I don’t want to talk to him right now.

Dr. Joy: Right, we are in mourning. So it felt like it moved very quickly from this news that her mom has now passed to then the next scene we see is Lawrence’s birthday. That was interesting that it’s like, oh, okay, I’m thinking we’re just focusing on the four friends and marking time with them but of course we get Lawrence thrown in too here. And again, we don’t know how much time has passed since Molly’s mom passed to when Lawrence’s birthday is. Because I was thinking maybe she was calling to tell him about Molly’s mom passing but clearly there was no conversation around that, so clearly there’s already been a funeral.

Again, we have no idea how long it has been since that happens but Issa is calling Lawrence to say happy birthday. And it feels like there’s awkwardness because it’s Issa. I mean like there’s just always gonna be some level of it. But there wasn’t any indication of like have they spoken since that night? It felt like, okay, we’re just catching up with any ex you might call on their birthday if you still want to say happy birthday to them.

Dr. Oriowo: I was under the impression that they did not speak because it was how she started the conversation with “I didn’t want to let too much time pass.” I assumed that there was a lack of speaking or very minimal speaking or like a sort of “passed by” text sort of thing. I also thought it was fitting that while mama is trying to convince Lawrence about being with Condola, that’s the moment Issa called.

Dr. Joy: Right. He like, okay mama, I’mma have to call you back. Also, we did not see Condola this episode which I thought was an interesting choice. Like so we see Jah, of course, but we didn’t see her at all, but clearly she’s still in the background. That conversation led me to believe that they are in a good place with co-parenting and now his parents are like, okay, are y’all going to get back together? Like what’s happening? But it does not seem that Lawrence is interested in that because Issa asks like, oh, can I take you out for your birthday? And we see he already has plans and another gorgeous girl walks in and says “hey, babe, are you ready,” kind of thing. Another sister that we had not seen, so Lawrence has yet a new boo who is gonna be taking him out for his birthday.

Dr. Oriowo: And I’m just like, well, she also hung up before he could say whatever he was going to say.

Dr. Joy: Right, like was he gonna say like can we get together tomorrow? We have no clue what was gonna happen.

Dr. Oriowo: Yeah, I was just like, argh! And then she called Molly and it went to voice mail. Which we see a couple of times.

Dr. Joy: A couple of times, right? Which was concerning, and so I expected that I would see some kind of pop up. Because, again, we don’t know how much time has passed. We see like Molly... and of course, she’s grieving, who knows like how she’s taking care of herself at this point? But it was concerning that we kept seeing her not there.

After Lawrence’s birthday, the next birthday is Kelli’s birthday. Kelli’s gorgeous, first of all, in this green gown. I’m like where can I get this? This is gorgeous. Oh my gosh, looking so queenly. And so she has this announcement at her birthday party that she is also expecting. And I’m like, well wow! Where did that come from? We have not had any indication, I think, around what was going on with her and her interest in having kids. But Issa then shares, oh, this is news. Like when did you change your mind? When did you change your mind around wanting to have kids?

Then she goes back to the Stanford reunion where they had her on the “rest in peace” list, basically, and talking about how that caused her... And that’s what we’ve seen much of her from this season, is like questioning her purpose and really kind of wrestling with some things about like whether she's happy with her life, what more does she want to do? So now we see clearly she has changed her mind about wanting to have kids and so she has chosen to have a baby with her new partner. And she has now also joined the firm. We hear her talking about the fact that she is at Molly's firm and taking care of business there.

Dr. Oriowo: Yeah. I do like the piece around the right to change your mind. And at the same time... We haven't gotten all the way to the end, but at the same time, I'm looking like did everyone need to wrap up with somebody and/ or with kids? For us to feel like things had closed out well and like they were secured, is that what we needed to see?

Dr. Joy: Hmm, interesting. I hadn't thought about that.

Dr. Oriowo: But again, I do like the right to change your mind. And that that change of mind doesn't have to do with, you know, family badgering you about the values of having a kid and all that other stuff. It seemed like something that she came to on her own, that she realized that she wanted to have this person's child and that's how she came to her choice that way. I mean, I also liked the progressiveness of her sexual prowess. That she's like, yes, I'm doing the butt stuff too, and I’m just like, alright now! I know that Issa didn't need to know it, but the sex therapy scene...

Dr. Joy: The sex therapist was very excited about this new information.

Dr. Oriowo: I feel like Kelli *[inaudible 0:36:34] me. Like from that Issa’s birthday where she was just like, when I have bad sex with a guy, I glare at him...

Dr. Joy: Oh my gosh, she's so hilarious, yeah.

Dr. Oriowo: I hope you have a conversation about the fact that the sex is bad, but it sounds like she's having good sex and she's exploring her sexuality, and that she feels safe enough to do so with the partner that she's with. And I'm just like I'm loving all of that for Kelli. Meanwhile, Issa had that sexy man. I was like, excuse me, excuse me.

Dr. Joy: I saw a lot of people talking about this and I also felt like he was like a Daniel copy. And so that also was surprising to me, that it feels like we saw everybody else revisit this season except Daniel. And I think that there are probably some reasons for that. Like we already got Nathan and Lawrence, do we need to also bring in Daniel who is who she cheated with?

Dr. Oriowo: Like we don't need that much mess.

Dr. Joy: Right. But Nasir definitely gave me Daniel vibes, so she did get her another gorgeous brother but it was not Daniel.

Dr. Oriowo: And that sexy ass lingerie set that she was wearing, I was just like... okay. But this is also the episode or that was also the part where we saw the last of mirror bitch, wasn't it?

Dr. Joy: I think so, that was the last conversation.

Dr. Oriowo: Yeah, like Lawrence calling when she about to go get some and mirror bitch is just like it's never gonna work... move on.

Dr. Joy: Yeah, and we also see, I think, her again talking about the fact that she's called Molly and hasn't heard from her. So I feel like they were three different occasions where we have like where's Molly? Like what is going on with Molly?

Dr. Oriowo: And Molly was not at Kelli's birthday.

Dr. Joy: No, she was not at Kelli's birthday. And so I feel like that is to mark the grief and like how you just fall off and you’re just trying to put the pieces together for yourself. But it was concerning that we didn't really know what was going on. But then we see the next scene is now we are back at Molly's birthday. So now the timeline is coming together because we now know it is at least a year since...

Dr. Oriowo: Since last...

Dr. Joy: Yeah, so Issa finally gets Molly on the phone, we see Molly in her office at the firm and it is her birthday and she's talking about the grief. Like about how sad it has been and how difficult it feels that she's gonna continue to have birthdays and her mom is not gonna to be there. Sharing some really I think real stuff about like what the grieving process looks like.

Dr. Oriowo: And I think too many of us have been sold on this idea of you'll get over it in a couple of months. And I'm just like there are birthdays and anniversaries where people are present and you expect certain things, and when those things don't happen, yeah, grief. You will still miss this person and that that is okay for you to miss that person.

Dr. Joy: Yeah. And I think this is where we see a glimpse of how the grief has impacted their friendship, because clearly it sounds like it's been a minute since they have caught up with one another. And at first, I thought is Issa in a new city? Like what’s happening here? That's kind of the vibe it was giving me. But no, it's just, you know, Molly says like life is lifing. And it feels harder to kind of be intentional about like catching up with your people, and like work is happening and I'm grieving, and relationships and all of this stuff. And so they're wanting to make a better effort to catch up with one another but it does sound like it has been some time since they last chatted.

Dr. Oriowo: Yeah, because I'm like when she was also saying that she was using work as part of her coping method, that she was able to focus on that and so that she was grieving a little bit differently. And that piece around like... I like that Issa reminded her that it's okay for her to not be okay.

Dr. Joy: Yeah, cuz they started off the conversation with just the celebratory happy birthday and then Issa’s like, how are you really doing? Which I appreciated. I felt like this entire finale was a lot of very tender moments between Issa and Molly, which I really, really love. Going back to the idea that they are the true love story that Insecure is about. Because it really feels like they have gotten into a really good groove in their friendship now of like what does the other person need? And like how can I show up for them? Which I was really, really excited to see.

Dr. Oriowo: Same. And the level of intention that they're putting in there, the effort that they were putting in. And seeing that at some point because life happens, that that means that sometimes one person's effort might change. It doesn't mean that they love you less, it means that they may not have the capacity at this time. And I think that a lot of us, we are in a space where we want to throw someone away when they stop having the capacity.

Dr. Joy: Right. Like everybody I think is doing the very best that we can to try to hold it together, so they may not have the same capacity they did at one point in their lives. And so at the end, when we see Molly and Issa talking for her birthday, we do see Kelli pop into the firm which indicates like she's clearly there now. Like when she checks with Molly. Like girl, don't worry about it, I can take care of it, you go enjoy your birthday, kind of thing. You know, so she is at the firm.

Dr. Oriowo: Can I just say, I love friends putting friends on?

Dr. Joy: Right.

Dr. Oriowo: Because I feel like we could get real caught up in this idea of the singular negro in the white space that we won’t tell a friend a secret or something that will help them. And I feel like we like to talk a little bit too vague about monetary things and I wish that we were a lot less vague. Because the only person that it serves for us to not give numbers is the office that's trying to hire somebody and lowball the hell out of them.

Dr. Joy: Indeed, indeed. Yeah, and even though this is a black firm, it is still like her giving her girl, like putting her on. Like she was the one, it sounds like, who initiated the conversation. Like hey, I got this friend who does this thing really well, what if we created an estates division? And we see now Kelli is there. I love that.

Dr. Oriowo: I love to see it.

Dr. Joy: Yeah. And again, I think a tribute to what Issa has done in her real life. Is like put so many people on, which we love. More from my conversation with Dr. Oriowo after the break.


Dr. Joy: Molly and Issa wrap up the birthday conversation. We see Issa now is in a workspace, so clearly she has gotten her own space for The Blocc, which is lovely. Which feels very much like that old... Like the flashback when we saw her life with Nathan or Lawrence. It feels like the workspace that we saw featured, at least in some of those ways, like these big windows and white walls and that kind of thing. It felt like, oh, wow, like she really did get a piece of what she was envisioning for her life.

Dr. Oriowo: Which is so exciting. And I like that she was, you know, like let me give you the tour. Or at least what is going to be in this space.

Dr. Joy: Lawrence just walks into the space, and I'm guessing maybe they had plans? It didn't seem like...

Dr. Oriowo: It’s not like she invited him.

Dr. Joy: Right. It didn't seem like he was just walking in like, oh, let me go check out Issa’s new space. It definitely seemed like she was waiting for him but it wasn't sure like why he was there. So again, we don't see everything but clearly she has invited Lawrence to check out the new space or whatever. She gives him a little bit of a tour, an idea of what she wants the space to look like, and they do some of this reflecting around like look how far you've come, you went from We Got Y'all to I got mine.

Dr. Oriowo: I must say, I do be loving their brand of corny, it’s cute.

Dr. Joy: It is very them. It is very them, yeah. We see, I think for the first time, this is an indication of like Issa feeling very confident in the decision she's made, at least in her professional career. She says I realized that no one was doubting me except for me. She has gotten to a place where she feels like, you know what, I have made the choices I feel like I wanted to make in my career and it is serving me well, and I'm open to seeing if this continues to feel like a good fit for me. And so she's talking about her career, I think, but clearly we see that this is also an opening or an analogy for the relationship between her and Lawrence. And so we see her end it by saying I'm open to finding out.

Dr. Oriowo: And I like that. Like I'm okay with finding out. I was not necessarily for this relationship... but that's not my relationship, that's her relationship. Fictional though it may be, it’s still hers, it's not mine. I’m just like, I like that it's like I'm gonna do what I can and I'm open to seeing whether or not we can create something with each other that feels sustainable and like we can be in it. And I also liked that she talked about the fact that sometimes you get worried about looking stupid, about wasting your time, and then you realize that, yeah, it is you. It's you in your way and that if you get out of your way, then you have a clear vision of where you're going.

I think for me, I’m just like the end of Kelli’s birthday, that's the last time we see mirror bitch and it ended with a middle finger. But it also seems to have at the very least sparked her to really reflect on her life and what she said that she wanted, and see all the ways that she has been getting it, to know that, okay, I've been putting off this thing with Lawrence and I'm ready to explore that thing.

Dr. Joy: Mm hmm. Yeah, it definitely seems like there's been a lot of thinking, a lot of like, okay, my professional life is kind of together and where I want it, now let me explore what this personal thing feels like. Like I've done a lot of thinking about whether this is something that could work for me. Clearly, they've been in conversation because he shows up at the office so it seems like they both are in a space of actually being open to exploring one more time whether this is actually going to work. And so then we do see a time marker, so they now give us a time marker that says one year later. And we are at a wedding.

Dr. Oriowo: Our first time marker.

Dr. Joy: Our first time marker, I feel like, all season. All season y'all ain’t gave us no time markers but now y'all want us to know it's been a year later. We see that we are at Molly's wedding, oh my god! Shout out to Cindy, our producer. You know, we have a production team group chat and Cindy threw out this like Hail Mary theory last week, like I think we're gonna see Molly and Taurean’s wedding. And I'm like, uh, I don’t know if I see that happening, because I didn't think we were gonna fast forward as much as we did, but shout out to Cindy because she was right. I'm guessing happened is that Molly got engaged for that birthday where we saw her last.

Dr. Oriowo: Uh-huh, where she was like Taurean left early and he *[inaudible 0:47:31]. I’m looking like ha-ha.

Dr. Joy: And I feel like Issa kind of knew but she didn't give us anything. So yes, I'm thinking Molly got engaged and so a year later now we see that she is at her wedding, looking gorgeous. Shout out to Shiona, I think is the costume designer who has kept everybody looking so incredible all season. But her wedding dress was gorgeous. Were you surprised that we saw Molly and Taurean getting married?

Dr. Oriowo: No, I was not.

Dr. Joy: You weren’t? Okay.

Dr. Oriowo: No. There was something about the way that it had already been moving forward that I was just like, well, excuse me. Growth. Like that letting go and the vulnerable conversation that they'd had about like, you know, people get tired of me, and how he was just liked but I'm not going to get tired of you. And just all of that stuff together, I was just like, oh, okay, this is it. I was very excited to see that for Molly and I will also say at the same time, I didn't need to. I would have been perfectly happy with the picture in the background or something else that said that this thing has happened. But I also liked that we were able to sort of see it and see what else had come to fruition, like Tiffany was pregnant.

Dr. Joy: Yes.

Dr. Oriowo: Or at least looking like she’s very due soon. But I'm looking like, don't they restrict your travel at a certain point?

Dr. Joy: Right. Who knows what was going on, it could have been twins. I mean, who knows at that point, right? Who even knows?

Dr. Oriowo: And Lawrence was still there.

Dr. Joy: Lawrence was not there initially. We didn't see him and I'm like, oh, okay, are they not together anymore? But then we see he had just gone to get her a drink, so they played us a little bit. Lawrence and Issa are clearly still together. And we saw the tribute table to her mom, which again, I felt very touched by because it feels like so much of the season–or the whole show really–was about her mom wanting to see her walk down the aisle, and I'm gonna be too old for grandkids, and that kind of thing. And so we see mom has not made it there, so I thought that that was a beautiful touch that we saw the tribute table there. I agree with you, I loved Molly and Taurean together, I just didn't think that we were gonna get a wedding out of the finale. But I did see like...

Dr. Oriowo: And a little touch of honeymoon.

Dr. Joy: And a touch of honeymoon. But I also think that her wedding set up the perfect kind of backdrop for this conversation between Issa and Molly. We see these wedding gowns are not like a one-person story, so you know you need multiple people to try to help you get into a wedding gown. I loved the reality of your girl helping you get out of this gown because you cannot do it by yourself.

And so it feels like it was the perfect backdrop for them to have this beautiful conversation, just about how their friendship has now progressed across these several years. From last season where we saw it to be really rocky, to this season where they have had some very real-life stuff and been there for one another. And so I think the moment of her saying, after she helps her out of the dress and they have this beautiful moment together, Molly says like I don't know what all life holds but I know I'm gonna be okay as long as you're here. And then Issa, as she's leaving, says I'm gonna step out and let Taurean take it from here. And so I think that is...

Dr. Oriowo: That part was so fast...

Dr. Joy: I know, right? Because it is very much like help you get out of the rest of these clothes, but also like you're giving your best friend away in a lot of ways. You know, to your earlier comment around even though it's joyous to get partnered and get married and the new life you're starting with your partner, there is this sadness around like your life with your girls is not gonna be the same. And so even if you still are very intentional about creating time together, it's just not the same. And so I think hearing her say I'm gonna pass it over to Taurean now was a reflection of that. Like, okay, I'm gonna step out because I'm not necessarily in this same role anymore.

Dr. Oriowo: Yeah. It made me think about that piece again around change and the gains and the losses. And, you know, I'm reflecting on my own and how that's basically what my maid of honor and my matron of honor said. Like they were giving me over to my partner and just the sadness that sort of came with that. Like, oh yeah, like things are gonna change. And at the very least, they still take time before you settle in and you're able to find a rhythm where you're able to work all the things together. So it's just like, yeah, it is a sadness and a joyousness and I love that piece around like thank you for loving me while I was me.

Dr. Joy: Mm hmm, yes.

Dr. Oriowo: There's something to be said about loving someone when they are allowed to be themselves instead of the version that you create, or the way that you might shame them for not being who you want them to be. And I love that we got to see that part because I feel like some people are most themselves when they are with their friends in a way that they cannot be most themselves when they are with their family.

Dr. Joy: Mm hmm.

Dr. Oriowo: Like the people that have watched you since you were a child have put all these hopes and dreams and desires onto your life a lot of times and, as a result, unable to see you fully in who you are, unless you have become the thing that they wanted you to be. And I'm looking like to know that you have been loved on being yourself, that's a beautiful joy.

Dr. Joy: Yes. And of course, the cast and crew were live tweeting and so it sounds like one of the takes was Molly and Issa and Prentice (who is the showrunner) told Molly (or Yvonne playing Molly), “Thank her as Issa Rae.” Like for how she has changed your life. And so what we see, and this was the last shot that Yvonne and Issa shot together, so this was really them like saying goodbye to these characters. Which made, I think, that scene just come to life in a very real way, because it was very real.

Dr. Oriowo: Yeah. I’m so sad...

Dr. Joy: I know, so beautiful. Yeah, so this is again where the waterworks have... I feel like I had been crying ever since her mom passed, but that didn't really stop, it definitely kicked up again here. And so we see that wedding scene wrap up and we see Issa... Do we see her in her office or just driving away?

Dr. Oriowo: Yes, we do...

Dr. Joy: She was in the office with this gorgeous power suit... Yes, yes. And we see her on this beautiful ride down the history of all of these places that have been meaningful to her. We see her stop at that We Got Y'all, we see her drive by the Best Buy that Lawrence used to work in and somebody is in the parking lot with a blue Best Buy shirt on... Yes. We see her, where else did she go?

Dr. Oriowo: We saw her go by her old apartment.

Dr. Joy: The old apartment and we see Thug Yoda outside playing with his baby. Yeah, so she is taking us on this beautiful ride through all of the scenery that has been the backdrop of her real life, I think, and also like the backdrop of Insecure. It felt nice to kind of like touch back on those places and to have this reflection of all of these things that have been meaningful, and how these things have shaped what my life looks like now. And so in this final...

Dr. Oriowo: That part right there.

Dr. Joy: Yeah, it was gorgeous.

Dr. Oriowo: Because I think sometimes we’re wanting to forget the past and I’m just like, don't forget the past. You bring it forward with you. All of those things helped to make you who you are in the present moment, so you can look back on it, you can remember things. Don't live in the past, you don't wanna live there, but you wanna be able to at the very least be like, yeah, I was there. I did do that.

Dr. Joy: You take it with you.

Dr. Oriowo: Yeah.

Dr. Joy: We see the final scene, she walks into this gorgeous apartment. Which is reminiscent of the dream sequence but is not quite the dream that we saw with the big white walls that we were like, oh, we love that apartment or that townhouse, whatever it is. And we see, I saw a picture when she walks in, of her and Lawrence. We see her, it's kind of fuzzy and we come into clear view and it is Lawrence and Elijah in the kitchen making a birthday cake for what is now her next birthday.

Dr. Oriowo: Mm hmm. Just like, wow, we got birthdays on birthdays on birthdays. And I was just very happy to see that red because I was just like, excuse me sis, showing off. The only thing that I probably wished that we would have seen or known or something is like Condola is Jah’s mom and being able to see that they are working to, all together as a functional unit. I feel like it's implied but not said, but that's cool.

Dr. Joy: Yeah, a lot was implied this whole finale. Right, the time travel can only give us so much at these birthday parties. And so, you know, it was very subtle but... I've watched the finale three times now and have also been paying attention to what people said online. It was very subtle but you also now see that Issa has an engagement ring on. We see her in a conversation with Molly, who is still on her honeymoon, and she makes a comment like is this what I have to look forward to? And you can see her in the mirror putting on her lip gloss and you can see that she has an engagement ring on.

Clearly, her and Lawrence are now engaged but we have not seen, again, we haven't seen the engagement. And in some ways, it feels like, oh! Like it feels like all this whole show has been about whether they were gonna get back together or not and then we don't see the engagement. But I also think, back to our earlier point around how that is great but it doesn't have to be the forefront of the story. You know, so making Molly and Issa and the friendships more a part of this finale as opposed to like just everybody getting engaged and married, I think was a choice and I think was good. Because I do feel like it's reminiscent of what they wanted us to get out of what the message of the show was.

Dr. Oriowo: Like, yes, we see Lawrence but the end is Molly and Issa talking to each other and that’s it. And broken pussy.

Dr. Joy: Shout out to Broken Pussy. I love that they went back to that, because that was clearly one of the highlights of Season 1. I love that they brought that back. But to your earlier point, too, we know that typically when we see Issa in a mirror, mirror bitch pops up, and she didn’t. And so there was not that need to kind of do that talking to herself. Though, of course, we all have still like a running tally of self-talk, but we don't see that as clearly as we have before. And your indication around it feels like there's some clarity there now, some confidence, some sureness that we see because mirror bitch is not there. That she is able to integrate that more into herself as opposed to needing to talk to herself in the mirror like that anymore.

Dr. Oriowo: Growth.

Dr. Joy: Growth. Kelli meme–growth. Yeah, so beautiful. You know, like you, I was also like I don’t know if we need to see them back together. But you cannot deny that they have like incredible chemistry. And so, like you said, it's not our relationship and so even though it may not be the decision we would make or whatever, it is clearly what they chose for themselves. And really, in the end, that's all that matters, is that they have made decisions that they feel like are the best for them.

Dr. Oriowo: You can’t ask for nothing more than that, right?

Dr. Joy: No. You get to try. You get to try and figure it out and see if it works. That's all we can ever want for anybody.

Dr. Oriowo: Yeah. I mean like, overall, this was a pretty satisfying ending. I was not disappointed. I definitely felt rushed maybe and I wasn't sure how I was feeling about that because it felt like everything was moving at such like this fast forward pace, but I think that some of that may also have been my own reluctance to see the show end. So placing some of that where it belongs, on me and not them, and just being able to accept what is, like Insecure is done and I think that they did a pretty damn good job closing out.

Dr. Joy: I do too. Yeah, I feel like I was expecting more loose ends and there really were none. Because usually you don't see things wrapped up as nicely, and that's what we’d kind of been predicting. Is that this will mirror real life and that we won't know what happens to everybody. Even though we don't know the full story, we know a lot of what is going on with their lives and so I think that that was an interesting choice that they made to wrap up so many of the stories, because I did not expect that at all. I thought we would have been left with far more loose ends than we were. But I appreciate it, I appreciate that it feels like we got a sense of closure and there isn't a lot of like guessing about what would have happened if.

Dr. Oriowo: Yeah. I'm like we get that and at the same time know that “and life goes on” because we didn't even get to finish the conversation that Issa was having with Molly. It was just over for us. Our being into their lives are done.

Dr. Joy: Right. I also think Issa is probably, as much as she loves Insecure and this has clearly been groundbreaking for her, I think she's ready to move on, like that is why she made the decision to wrap it up at five seasons. There's just so much more that she wants to do and so I think this ending also closes the door for fans to be like, well, can we get a reunion episode in five years? Though there may still be the longing for that, I do feel like the closure has happened with these characters enough to where she can also move on into her other creative pursuits and really put a bow on Insecure.

Dr. Oriowo: Word. I'm looking like you can't ask for five-year nothing. You got three years of information already.

Dr. Joy: She gave you all kinds of flash forwards...

Dr. Oriowo: Besides that *[inaudible 1:01:47]. But this is that point that I feel like it comes back to that piece around when you say you're finished, you're done and that that's okay. And that you get to pivot from there. And it was nice to know that Issa Rae, not just Issa for the show, not just Issa Dee, but it's just like I am done with this thing and I am ready to move into these other things that I'm also wanting to do. And I realize that in order to do those things in the way that I want to and to honor them, I have to let this go. I have to make room in my life for the next phase. And I think that too many times we get caught up in trying to keep all the things, but some things we could let go.

Dr. Joy: We can let go and we can wrap them up nicely. And again, a lot of the commentary online has been around how a lot of our shows don't get this...

Dr. Oriowo: They just get cut off.

Dr. Joy: Right. Myself included, I'm still salty about the fact that we didn't get like a Girlfriends resolution. Like I am still waiting and hoping somebody will greenlight Mara Brock Akil for a Girlfriends movie so that we can get the proper goodbye to Girlfriends. And so I think it is really beautiful that they got five seasons. I'm sure HBO would have given them as much as they wanted because the show is doing well and so they didn't have to end it at five, but they made the decision like this is where we feel like will be a good place to end, and so we're gonna wrap it up here. And a lot of shows aren't afforded that and so I just think it's cool that they even got that opportunity.

Dr. Oriowo: It's nice that this got to end and it got to end on their own terms, as opposed to on someone else's times.

Dr. Joy: Yeah. This was very much on their own terms, which it feels like the whole project had been, so kudos to them. And you know, just so much love to Issa and the entire team for giving so many people opportunities and there's just so much content. Even these episodes of the podcast would not be happening without the wonder that is Insecure, and so I just am so grateful and like humbled that Issa has been giving of herself and like creating this thing that I think has just given permission for other people to share their stories. I want people who are listening to like not be sitting on these ideas because the other thing that I think is so beautiful about Insecure is that it was just so super regular. Like these were not kings and queens we were watching or super moguls or celebrities. They were just like regular...

Dr. Oriowo: This could have been us.

Dr. Joy: Which is what I think made the show so successful, is that we were able to see ourselves or our friends or our family in these characters. And so that I think is just permission for other people to just stop sitting on your ideas and share these stories. From YouTube to here, you just never know what can happen. And so I think that it is just an invitation for people to share their gifts and their stories with the world.

Dr. Oriowo: Absolutely. Like please don't sit on it. I’m looking like we’re ready.

Dr. Joy: We are ready. We’re trying to do...

Dr. Oriowo: Joy, I’ve been asking about this book, right? I’ve been asking you for a book.

Dr. Joy: The book is coming. The book is coming.

Dr. Oriowo: You know me, shady as ever. I’m just like I feel like I can see way in... And I feel like these things they're coming and don't sit on it. Like, yes, we can worry about failing and people not coming to the thing that we have or whatever that looks like. Yes, be concerned around that but don’t let that stop you.

Dr. Joy: Right, right. You’ve got to start somewhere.

Dr. Oriowo: And don’t let that stop you from telling people, too. Like, oh, it’s gonna be three of us in there. I’m looking like if it’s gonna be three, let it be the best small ass workshop you ever put on.

Dr. Joy: You just never know.

Dr. Oriowo: Exactly. Don't tell yourself no. Let other things tell you no and then figure out. Work out how to get the yes, within reason.

Dr. Joy: What's the pivot gonna be? Yeah, after you start, but you gotta start. You gotta start before you can pivot because there can be no pivot if you don't put anything out there.

Dr. Oriowo: Amen. I remember my first Goal Planner workshop, nobody signed up. It was complete crickets. Nobody showed up, no one came. I was just like, well, here I got all these magazines, I got all this stuff and nobody's here. But I could have just stopped there but I didn't. I love goal planning so I just had to goal plan my goal plan and rethink the vision.

Dr. Joy: Right, I love it.

Dr. Oriowo: Like, we can't be afraid to fail. Fail up. Fail now and fail up later and you just keep getting better till you stop failing, I think.

Dr. Joy: Right, but you gotta start. Again, it all comes back to you just starting somewhere.

Dr. Oriowo: Yeah.

Dr. Joy: I really appreciate you spending your weeks with me recapping. I feel like this has been so much fun. I am sad that we will not have this but I feel like we will find something else. And again, you’ve been on the podcast to talk about other topics so we know you won’t just be here to talk about TV shows, but I feel like there may be another show at some point in the future that we can get back together to chat with. But I do appreciate you giving up your time.

Shout out to all of y’all who are in our tweets and on Instagram saying we can’t wait to hear what Dr. Joy and Dr. Donna are gonna be talking about this week. We appreciate y’all for listening and sharing your thoughts and questions and comments with us. And you will definitely hear Dr. Oriowo on the podcast again because we have great conversations and she has great insights. Again, thank you.

Dr. Oriowo: Thank you for having me. I’m gonna miss this. It’s like the baby, end of an era.

Dr. Joy: I know! It has been so much fun to do these episodes with Dr. Oriowo. Be sure to visit the show notes at to find out more about her work or to grab a copy of her workbook or to register for the goal setting workshops she will be facilitating in January. And don’t forget to text two of your girls right now and tell them to check out the episode. If you’re looking for a therapist in your area, be sure to check out our therapist directory at

And if you want to continue digging into this topic or just be in community with other sisters, come on over and join us in the Sister Circle. It’s our cozy corner of the internet designed just for black women. If you’re free on New Year’s Eve, we’d love to have you join us for our self-care room where we’ll come together virtually to reflect on the year, play some games, and celebrate with one another. You can join us at Thank y’all so much for joining me again this week. I’m wishing you and your family a very healthy and restorative new year, and look forward to continuing this conversation with you all real soon. Take good care.


Discover the transformative power of healing in community in Dr. Joy Harden Bradford’s debut book, Sisterhood Heals. Order your copy now!

Sisterhood heals
Order Now

Looking for the UK Edition?
Order here

Discover the transformative power of healing in community in Dr. Joy Harden Bradford’s debut book, Sisterhood Heals. Order your copy now!

Looking for the UK Edition? Order here