Season 5, Episode 7, ‘Chillin’, Okay?!’
There is something about spending an entire day with your girls, in the house. Things come out, love is passed around, laughter is shared and there is a warmth that comes from all of that friction.
“Chillin’, Okay?!” starts at Issa’s apartment, where Molly, Kelli and Tiffany have met up to start a day of relaxation for Molly, who has been stressed because of her mother’s health crisis. They had planned to meet at the house and then head to a spa, but when a pipe bursts at the spa, they are forced to stay home until dinner.
Disappointed, the girls start drinking and forget about the spa. Tiffany starts to play “Last Night,” by Diddy and Keyshia Cole, Molly starts to dance and pretends her wine bottle is a microphone. Issa suggests they play Questions in a Hat, where anonymous questions are thrown in a hat and randomly selected by players, but Kelli is skeptical. “You know the power it has,” she says sinisterly.
Questions in a Hat is less a game than an icebreaker exercise, designed to make the mind feel comfortable while exposing vulnerabilities. Even though the girls are friends and have become closer throughout“Insecure,” there are still things that need to be tugged out of them, like when Molly admits to having never seen “Love Jones” (guilty!) even though she bonded with Issa over the movie. Or when Tiffany admits to thinking about her husband when she masturbates.
When deeper questions start to come up, Issa explains that she and Nathan are not in a good place. The girls listen and check Issa. That is what sisterhood is for: To let you know that yes, maybe you are inconsistent and maybe your boo is not wrong. The ladies are perfect at it — funny, calm and just harsh enough.
Issa says she is willing to start over, to let go of what she has with Nathan, but no one believes her — not her girls and not the viewers. She also admits to feeling bad because Nathan has not returned her “I love you.”
Molly then draws the “If you could have one do-over, what would it be?” question.
Issa has been thinking about her own do-over since she noticed that Lawrence moved back to Los Angeles. She has been considering reaching out to him for closure, she says, which she hadn’t shared with her friends.
“I just wish I figured out what I wanted to do sooner,” she responds to Molly’s question.
Later on, while Issa’s friends are ranking her lovers — Daniel for the win — she tells the girls that she saw Lawrence, Condola and Elijah at the hospital. Condola and Lawrence seemed like they were doing well, so Issa assumed they had rekindled their affair. But Kelli lets her know that things were not great with them at Tiffany’s child’s birthday party.
“Really?” Issa responds, as if she were trapped in a hot car and a window had just magically opened. She tries to make the case for how she feels to her friends.
“You made the smart choice,” Molly reassures her.
“Sometimes it’s not about making the smart choice — it just has to make sense to you,” Tiffany says.
Issa’s eyes light up. Tiffany’s comment validates her feelings — she’s looking for any reason to run back to who she knows and what feels safe. Things are shaky with Nathan and that instability can be exhausting. Sometimes you just need to be loved and supported.
After the girls decide to stay in for the night, they cute up the balcony with rugs and throws and pass libations around. When Dro, the messiest of all “Insecure” men, calls Molly, Issa sees it as an excuse to call Lawrence, though she has no plan for what to say. Molly snatches her phone and hangs up.
“Girl, you know I love you right?” she asks, and then reminds Issa about the earlier discussion of her inconsistency. “You’re doing it — like how is this going to help?”
While Issa was thinking about backsliding toward Lawrence, the man himself was trying to repair his relationship with Condola. Issa has not realized — or is choosing not to consider — that Lawrence has a world of his own to take care of right now. A baby doesn’t care about Issa’s need for closure or even what Lawrence wants at all. It isn’t like before; starting over for Issa now means leaving safety totems like Lawrence behind.
The next morning, Nathan calls and tells her that he loves her and that he knows he can be avoidant and childish. (I cannot confirm that calls like this happen in real life.) He promises to do better and she hangs up with a smile on her face. Then Lawrence returns her call from the night before. She does not pick up because she does not need a security blanket anymore.
While there’s still part of me that secretly would like to see Issa and Lawrence end up together in the series finale, what I really want is for Issa to choose herself and the things she wants out of love, not desperation. I want her to chill, OK?