Old Loves is the fourth episode Season 5. It was directed by Jesse Peretz, and written by Bruce Eric Kaplan. The episode orginally premiered on March 13th, 2016.
Fran and Hannah are hanging out at home when Fran starts looking over her graded assignments. Hannah went for a creative approach with the kids and told them not to worry about grammar rules; Fran is basically calling her teaching methods into question. The female student's name on the paper is Maile. Fran can't pronounce that unusual name and Hannah tells him "she does not like to be called "'Male.'" Fran starts circling misplaced adverbs and other annoying stuff on Hannah's papers until Hannah tries to take one paper away from him, and rips it in the process.
At school the next day, Maile, the student whose paper got destroyed, comes up to her and asks what happened to the assignment. Hannah marches the student to Fran's classroom and makes him explain what happened to the paper and why it's all torn up. It turns into an even bigger fight between Fran and Hannah, with Hannah wanting him to apologize. Maile ends up leaving in tears.
Meanwhile, Marnie and Desi have returned from their honeymoon and to their very real-life couple problems. Desi has decided, without Marnie's input, to build a wall in their apartment so that they can have a little more privacy and personal space. Marnie flips out and tells him that she just wanted a bigger apartment. They have a big fight about it and ultimately, Marnie is furious.
Downtown in Tribeca, Adam shows up at an AA meeting that Jessa is attending: She's started going to women-only meetings in order to avoid him. He's totally aware of that and calls her out on it; she reminds Adam that the reason that she doesn't want to see him because whatever might be happening between them would create problems for her relationship with Hannah. Adam calls bullshit on that move, adding that Hannah wouldn't think twice about going after a guy even if it would hurt one of her female friendships. He calls Jessa a pussy and walks away.
Back in Brooklyn, Ray and Elijah are talking about Elijah's upcoming date with Dill that evening. He's clearly all freaked out about going out with the famous journalist somewhere fancy in the theater district. He's excited, too, because he's going to be meeting some of Dill's friends for the first time, which means something important to him in terms of the way that Dill is representing their budding relationship.
Hannah and Marnie both wind up at Jessa's appointment later in the afternoon to escape their respective partners. Jessa isn't happy to see them in the least: She's busy studying and they're having a big relationship talk on her bed. Marnie encourages Hannah to work things out with Fran. In the process, she realizes that she has to be less nitpicky in her marriage if it's actually going to work out. After this revelation, Marnie goes running home to make up with Desi while Hannah stays at Jessa's; even though it's pretty obvious that Jessa doesn't want anything to do with her.
Marnie heads back to her apartment, where Desi is having a total manic meltdown. She apologizes for upsetting him and thanks him for doing this nice thing for her.
Elijah later heads into Manhattan for dinner with Dill. They're seem to be having a truly excellent first date, but Elijah keeps looking at the door, keeping an eye out for Dill's friends to show. Dill notices and asks him what's up. Elijah confesses that he thought they were meeting people, but if this is the sort of relationship where they don't meet each other's friends, that's okay. Dill tells him that he shouldn't be okay with that kind of relationship and that he should expect more respect. Seconds thereafter, his friends show up.
After dinner, they end up walking around Times Square together, snapping pics with tourists and kissing.
Hannah and Jessa wind up going out for rice pudding. Jessa is being super antagonistic, which Hannah can't help but notice. She's also just being straight-up mean. The amateur psychologist in me thinks that she's sabotaging the friendship so that she can be with Adam — and also working out some latent resentment about Hannah needing so much friendship. Hannah presses the issue of what's going on between them and Jessa says that maybe they just shouldn't be friends anymore. Hannah storms off with her rice pudding to her apartment. Even though she and Fran are still not talking.
Jessa leaves that encounter and goes straight to Adam's apartment, where she confesses what happened with Hannah and also that she's wanted to be with Adam for a really long time. They end up having sex on the couch, though, it's super-awkward, and then pass out together.
- The name of the episode refers the Old Loves tumblr, which shows former celebrity couples.
- The kissing scene between Elijah and Dill took place in the real Times Squares. So a lot of the people seen walking and taking pictures in the background weren't extras.
- Hannah's long-sleeved dress that was worn for the majority of the episode is actually a vintage piece.