Welcome back to the season finale of Season 4 of HBO’s Insecure.
Executive producer Penny Prentice who wrote and directed “Lowkey Lost,” the final episode of Insecure season 4, kicked off the closer with Issa (Issa Rae) shopping at the blackest farmer’s market in Los Angeles. Even the fruit pies from CobblerMania feature Mother Africa. We then see Issa inquiring about the price of happy flowers versus funeral flowers when Lawrence (Jay Ellis) walks up to her with an update about his prospective new job.
“It looks like I’m going to be a trolley n*gga,” a smiling Lawrence tells Issa. She congratulates and hugs him and promptly misidentifies San Francisco as “the Windy City.” When Lawrence corrects her, Issa says Chicago should be called the chilly city because it’s so cold and Lawrence sarcastically asks if Issa went to school. Not one to be outdone, Issa asks Lawrence if he wants to have congratulatory sex or not. Lawrence smiles and says he does and the subject is changed. Issa tells Lawrence she is so proud of him and Lawrence beams as he talks about having his own team, a corner office, and an assistant.
Lawrence then asks Issa if the long distance will be a deal breaker and she says it won’t. She says San Francisco is only a 45-minute flight away from Los Angeles and says that if things stay good between them, she could even see herself moving to the Bay Area. An incredulous Lawrence asks about Issa’s job, family and friends and Issa says she can make new friends. Considering her rocky friendship status with Molly (Yvonne Orji), Issa adds that she might need to make new friends. Issa then says she wants to cut out the BS in her life and surround herself with things that make her happy, like Lawrence, and believes if they want the relationship to work, it will work. Lawrence agrees and says he wants the relationship to work too. They smile and kiss and Issa tells Lawrence to have his new assistant call her assistant. And then she vetoes that suggestion and admits that she needs to pay her assistant Quoia (Courtney Taylor) first.
The next scene takes place at a work mixer for Molly’s job. Andrew (Alexander Hodge) is by her side and he is sizing up the crowd trying to figure out which guy is Molly’s work nemesis, Taurean (Leonard Robinson). Andrew figures out who Taurean is based on his turtleneck and overuse of hand gestures. Molly concedes and laughs but says that when she described Taurean as the “black Elizabeth Holmes,” she made the guessing game too easy for Andrew. BJ (Norman Towns) walks over and wonders if Felicia (Kelsey Scott) normally dances like that at all the firm’s get-togethers. Molly jokes that Felicia has probably had too many mimosas and then introduces her coworker to Andrew. BJ invites them to an afterparty of sorts but Andrew doesn’t seem too interested. Molly convinces him to go but Andrew seems tired of compromising. Uh oh.
Cut to Leimert Park where Nathan (Kendrick Sampson) works as a barber. Issa walks into his shop to meet him and Nathan tries to introduce her to his coworkers but they ignore her. Issa shrugs it off as fatigue and Nathan shows Issa to an adjoining room filled with more barber chairs and stations. A thrilled Issa says she can totally see throwing an event there and Nathan is pleased. As Issa takes photos of the space with her phone, Nathan takes the opportunity to apologize for dissing Lawrence. Nathan says he knows that he messed up his relationship with Issa but admits that hearing that Issa had gotten back with her ex angered him more than he thought it would. Issa apologizes and says she wants to be a good friend to Nathan but she’s with Lawrence now. She hopes it’s not too much to handle and Nathan says it’s not. Nathan says he just wanted to be honest about how he felt and the last thing he wants to do is make Issa’s life more complicated. He then lightens the mood by asking if Issa really ate lunch in a closet when she worked at We Got Y’all. Issa says she ate breakfast in there too and she named all the mops and they both laugh.
Now back to Molly and Andrew. The couple return to Molly’s apartment and she complains about drinking too much beer. Andrew wants to watch the Looking for LaToya reunion episode but Molly says she wants to lie down. Andrew says he will watch and try not to spoil it for Molly and she says she doesn’t want him to watch without her. Andrew sighs and says, “Of course. We’ll do it on your schedule.” This shocks Molly and she asks Andrew to clarify. He says that if he had wanted to stay out the way they did for Molly’s work shindig, it would’ve been an ordeal. Molly says Andrew didn’t like when she worked late but now that she’s trying to include him in her work life, he’s still unhappy. Andrew says that Molly is dismissive of his feelings but constantly wants him to bend over backward for her. He then brings up the fact that Molly didn’t try and work things out with his brother and Molly says she thought they have moved past it. But Andrew argues that Molly is the one who is unable to let things go. Molly’s phone starts ringing and it’s Kelli (Natasha Rothwell). She ignores the first call to continue her argument with Andrew but when Kelli calls again, Molly answers and learns that Tiffany (Amanda Seales) is missing.
Molly rushes over to Tiffany’s house where Kelli and Issa are trying to comfort Derek (Wade Allain-Marcus), who is yelling at an employee at the movie theater at LA Live. He’s hoping someone at the theater has seen Tiffany. Turns out, Tiffany called Derek the day before and said she needed a break and then turned off her phone and disappeared. Tiffany’s sister Ashlee (Shvona Lavette Chung) and mom Gloria (Tara R. Cook) are there too but Gloria is mumbling about strange dreams and driving Kelli crazy. Molly asks if they’ve called the police but Kelli says they have and the police told them to wait. Derek says he’s not going to wait any longer and decides to go to the movie theater himself. Kelli, Molly, and Issa decide to go too.
The quartet arrives at the theater and split up. Kelli talks to the security guard (played by director and writer Penny) and Derek goes to find the manager. That leaves Issa and Molly looking at each other awkwardly before deciding to split up and visit the concession stands on different floors. Having learned nothing, the four reconvene and Kelli notices that the theater has a bar. The bartender tells them Tiffany drank four margaritas and then left to get food in a Lyft. Derek remembers seeing a Lyft charge on his phone and shares what little details he has with the group. Based on the Lyft charge, Issa is able to surmise which Mexican chain restaurant Tiffany went to because she’s a Lyft driver. Excited about the lead, Derek and the gang race off to the downtown eatery where a manager named Ronald (Bernardo Badillo) tells them he doesn’t remember Tiffany. But Molly sees that there are surveillance cameras and a reluctant Ronald agrees to share the footage. They watch and eventually see Tiffany getting her food and leaving to hop on a nearby bus. If she took the bus, Derek deducts, then she must be staying at a hotel nearby. All four hop on the bus and Molly and Kelli start making calls. As they wait to see if Kelli has better luck than Molly, Derek reveals that he knew Tiffany wasn’t happy. But he says he thought time would help. He also says he didn’t know how to fix things with Tiffany and that when he tried to bring in help for the baby, she shut him out. “I just didn’t think it would get this bad,” Derek says before Issa says that he’s done so much to support Tiffany and he’s a great dad. Issa says Derek even gained five pounds of sympathy weight but Derek says it was actually 15 pounds. “None of us are perfect. We’re all just trying to figure it out,” Issa says, causing Molly to look at Issa as if she finally understands her side of things.
An overly interested white passenger (John Frost) sees Kelli waiting on hold on the phone and tells her that his inner black woman looks like Kelli. But Kelli isn’t having it and tells the dude to STFU. Offended, the man facetiously tells everyone to “Shhhh!” because Kelli is on the phone. Before Kelli can curse the man out, she finds out that Tiffany is staying at the Sheraton just as the bus passes it by. Kelli and the crew jump up and beg the bus driver (David Raibon) to stop and let them off but he chooses to be difficult and says he can’t let them off. After a little back-and-forth, Kelli spots the emergency exit button and the driver tells her not to touch it. Issa urges Kelli to push it and Kelli defiantly does just that. The bus driver waves down a nearby police car and two white cops stop Derek, Kelli, Molly, and Issa as they search for the hotel. Kelli dares the cops to Taser her and Derek confesses that Tiffany told him Kelli urinated on herself when she was tased in the past. Kelli tells Derek to change the subject and Derek tells the cops they’re just looking for his wife. Molly tells the officers she is a lawyer and asks why they haven’t questioned the white couple who was also on the bus. Aware of the optics, the lead white cop (Matt Cordova) says he’s not getting in trouble and tells everyone to disperse, including the bus driver.
Derek, Molly, Issa, and Kelli finally reach the hotel and find Tiffany’s room. Before knocking on the door, Derek tells the ladies he just wants Tiffany to be alright and then he knocks to see if she’s inside. Tiffany asks who it is and Derek asks her to open the door. She opens the door wrapped in a towel. Tiffany’s hair is wet and she apologizes and says she didn’t know what else to do. Derek hugs her and they cry together causing Kelli and Molly to cry too.
The sun rises and it’s a new day. Breathtaking aerial shots of Los Angeles, including a Kobe and Gigi Bryant wall mural and a Nipsey Hussle pavement mural, are shown before the camera cuts to Andrew’s house. He and Molly are having coffee and talking. Andrew asks how Tiffany is doing and Molly says she is ok even though things are rocky. Molly apologizes for leaving in the middle of their argument but Andrew says he understands. He says they don’t have to talk about their relationship now because he knows Molly had a long night searching for Tiffany but Molly says she doesn’t mind. She wants to address what’s wrong so that things between them don’t get worse. Andrew says they’re not on the same page.
Molly says she should’ve gone with him to the Clippers game with Andrew’s brother and says sorry but Andrew admits that they have other problems too. He says he’s been feeling this way for a while and wonders if they’re just not a good match. Molly says neither one of them has been in a relationship that long and that has to mean something. Andrew argues that although that is true, no relationship should be this arduous. Ouch. Molly asks if they put in all that time for nothing and even volunteers to go to couple’s therapy. But Andrew stops her and asks what she is fighting for and if their relationship is what she really wants. A teary Molly is rendered speechless and before she can answer Andrew, the camera cuts to an exterior shot leading to Issa’s place.
Lawrence is knocking on Issa’s door and she answers. They hug and kiss hello and Issa says she didn’t get any sleep because of their search for Tiffany. Issa makes a joke but Lawrence isn’t laughing. He has bad news. Condola (Christina Elmore) is pregnant with his child and she’s keeping the baby. Gut punch. Condola says even though they’re not together, she wants to keep the baby because she still wants kids. Lawrence and Issa agree that it’s a lot and he says even though he and Condola are still processing everything, he wanted to be honest with Issa. She naturally asks if he and Condola are getting back together and Lawrence says no. He says he wants to be with her and Issa reminds him that he’s having a baby with Condola. Lawrence says he didn’t plan this and says he didn’t want this to happen. Condola is shown saying she doesn’t expect anything from Lawrence and she doesn’t want him to feel trapped. She says he can be as involved as he wants and says, either way, she is going to be good. A teary-eyed Issa says she thought things were finally working out and she and Lawrence sit in stunned silence.
We don’t know what Issa and Lawrence decide but in the next scene, Issa is shown walking around her place and smoking a joint as Moses Sumney’s “Keeps Me Alive” plays and breaks what’s left of our hearts. When day gives way to night, Issa walks into her favorite Ethiopian spot and meets Molly for dinner. They both have a lot to tell the other and Molly says she is glad Issa came and Issa says she is glad Molly called. Well, at least these sisters are friends again. God knows they need each other. The camera fades to black and Tyler the Creator’s “Are We Still Friends?” plays while the credits roll. Wow, what an amazing season this was. See y’all next year hopefully.
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Mekeisha Madden Toby is a Los Angeles-based, award-winning journalist who has been covering television and entertainment for 20-plus years. The Detroit native, wife and mother has written for TV Guide, Essence, CNN.com, Variety, The Detroit News, Shondaland.com, espnW and more. She has been a BGN contributor since 2013.