Carrie starts this episode off musing about boundaries, and she can't wait to go from Intern to Writer. All summer long, Carrie has been working on story pitches and she's feeling optimistic. She has narrowed her ideas down to just one: a story on a young playwright. Her New School writing class (oh, guess she got in) talks of nothing else. He wrote about his dead brother, which Carrie finds inspiring and Bennett suspects is manipulative. Then, some guy in a suit walks by and is like, "you are adorable" to Walt in a voice that doesn't match his age. Bennett says it sounds like Blake is asking Walt out and it puts everyone on the spot.
Meanwhile, Dorrit is ready to get down with her boyfriend Miller. Miller says he doesn't love Dorrit's twin bed, so she beckons him into Carrie's room.
Walt tells Bennett that the situation with Blake was weird for him and Bennett says, "rules are rules and I've always said we're not exclusive." Ugh, he's doing that horrible thing that straight men do where you have to go out with other people even when you'd rather not. Bennett encourages Walt to go on the date.
At Sebastian's house, where no one cares, Sebastian's dad is out of town again. I feel nothing. Back to New York!
Carrie pitches her story idea to Larissa, who says, "He's 19, he's dealt with death and he's probably gorgeous, which makes him right up your alley." Her enthusiasm for life never fades. She notes that there are pieces on him all over town, but Carrie says hers would be more of an in-depth interview. Larissa says if Carrie gets an interview she will publish it, but the playwright is notorious for not giving interviews. I'm sure Carrie will get one, practically with charm alone.
Carrie and Bennett wait in line for Adam Weaver's new play and Bennett brings up that Weaver is probably gay. Bennett says he'd work that angle anywhere short of sleeping with the subject. It becomes a challenge for who can get the story.
Back in school, where Carrie just doesn't go anymore, I hope? Walt tells Mouse of his non-exclusivity woes. Mouse encourages Walt to date other people, too. Maggie swings by and they lie and say they're talking about Sebastian. No one has anything better to do, usually, so Maggie believes it. They realize that Sebastian has also been out of school. He is at home, being sad about his daddy issues and yearning for his older lady lover.
In the play, an actress doing terrible prop work makes Carrie laugh. It's a sad part of the play, so everyone is annoyed with her. Carrie can't stop laughing, loudly, as more and more props are thrown "overboard" onto the hard stage.
Tom is doing really well as a big-shot lawyer. His clients like him better than Harlan, who shouldn't be working in this city anymore. Tom offers all his phone numbers to this client, offering small-town style service in the big city.
Leaving the play, Adam Weaver leaves the building and is staring at Carrie. He walks toward them and acknowledges that Carrie was the person laughing during the funeral scene. Carrie says she also laughed inappropriately at her mother's funeral, then proceeds to tell the story. Weaver says he loves that Carrie laughed, because the scene is supposed to be funny. He is very cute, and Carrie totally gets him. Weaver invites Carrie out with his friends for a drink, hopefully to a bar where they don't card.
At said bar, Carrie drinks a beer with the adorable playwright. She asks him to talk about the play and he asks if she wants to play Quarters. She's aware that he keeps trying to change the subject whenever she wants to get a little personal information. He says everything he wants to say is in his plays, but offers to tell Carrie something personal if she tells him something about her. Look, Weaver is setting up some boundaries.
Tom meets with Barbara, Harlan's assistant, who is like, "what's a weekend?!" He says that his daughters are going to meet his girlfriend's son for the first time because we have to fit another story into this episode. Tom tells her what happened with that big client and she says he will likely regret giving them his home number. Firms like them don't think twice about eating your life up, Barbara says. Tom should have established boundaries.
Sebastian lies on a leather couch with his hot, frustrated housewife lover. She asks him about school, stroking his hairless chest. Sebastian tells her his Carrie woes and about how he let her go. Vicky says he seems like he's really in love with her, and Sebastian supposes he always will be. Vicky says love does not get easier, then they make out.
At the bar, Carrie finally gets Weaver to reveal a little more about the play. He admits, off the record, that at the real funeral he laughed the whole time and his dad punched him in the face. They haven't talked since. They bond over having experienced death and then they kiss off the record but who cares, he is so cute.
The day, Carrie calls Larissa to tell her she made a terrible mistake. Larissa, who has eyes and ears everywhere, heard they were getting cozy then left together so Carrie must have gotten some really good stuff. Carrie says it was cozy and juicy but he told her stuff off the record and Carrie has qualms about using it. She admits to kissing Weaver, and Larissa calls her sense of morals "adorable." Larissa encourages her to sleep with Weaver to get a story.
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Carrie hangs up the phone and gathers with Tom and Dorrit to meet Deb and her son, Dylan. Dorrit is sour, but warms to Deb's Godfather joke. Dylan looks like he's going to be trouble, or just a regular little asshole like kids his age can be?
Meanwhile, Maggie stops by Sebastian's house and invites herself in. She offers Sebastian some company, but then Vicky comes downstairs in no pants. Maggie leaves, and Vicky tells Sebastian she has a crush on him. It's all very weird, and none of it matters.
Walt shows up at Interview and runs into Bennett and feels awkward about it because he's there to meet Blake for a very expensive dinner date. Blake arrives and hugs Walt, which causes Bennett to drop his papers for some reason?
Pizza dinner with the two families continues and Dylan plays a video game the whole time. Maybe he has autism? He says he only wants tater tots and when Carrie says they don't have any, he yells "TATER TOTS." Deb pulls some out, saying he won't eat anything else, and he reminds her to give him ketchup. Maybe he has only been this way since he saw Tom naked last season.
Carrie says she'll go upstairs to get Deb some copies of Interview magazine, but looking for those copies she discovers a condom wrapper. She confronts Dorrit about it and she's like, "yeah, duh." Carrie says she's glad they're being safe but is upset they did it on her bed. Dorrit assures Carrie they put down a towel, but that makes nothing better. Dylan walks by and shouts, "you have a rubber, rubber, rubber, rubber!" and where he learned that gross word for condom I do not want to know.
Suddenly much less autistic, Dylan walks into the room and pulls out a pair of underwear from Carrie's top drawer. Carrie asks him not to do that, and he says they need to be nicer to him if they don't want him telling everyone about the rubber. Carrie asks him to stop saying rubber, and I agree. Then, Dylan says he wants to see "Jugs, J-U-G-G-S and I wanna see 'em now." What in the actual fuck.
Dorrit starts unbuttoning because she doesn't care if a pervy kid sees her boobs, but Carrie has a better idea. They threaten to kill him with a wedgie, and it seems to do the trick. But he runs to Deb to tell her, of course. They say they were just telling a story, and subtly threaten to tell Tom and Deb about Dylan's demand to see their boobs. The kids go to make sundaes in the kitchen and Deb says that Dylan never lies.
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Just then, Tom gets a call from his new clients. Dylan is on the other line, shouting, "rubber, rubber, rubber, boobies, boobies, boobies, juggs with two Gs!" into the phone. Maybe Dylan will die at the end of this episode.
Blake and Walt's date is starting and Bennett is found waiting for them at the restaurant. He says he does not want Walt to go on this date because they are dating and Blake is like, "huh?" He says he doesn't like being put in the middle of this office romance drama and leaves. Walt and Bennett hash it out, admitting their feelings. Bennett says he wants to be exclusive and Walt plays it cool. They kiss and now they're exclusive. Boundaries.
Back in rubber-ville, Tom and Deb admit they have to talk about their kids. Deb is like, "what are you going to do about Carrie and Dorrit? They were really mean to Dylan," and that is the perfect time to dump her, Tom. She says Tom's daughters are immature and won't hear of Dylan's phone fart noises. They need to have a bigger talk.
Carrie and Weaver go out again, with Carrie telling her whole story. Weaver opens up to Carrie about his relationship with his brother, which was rather competitive. Carrie could be getting her scoop, because Weaver forgot to say "off the record." Weaver admits that his brother's death made him and he doesn't even miss him. He says he's a monster, and Carrie comforts him, her narration saying she realized she couldn't write the story.
Carrie and Dorrit console Tom about things not working out with Deb and he says he could never be with someone so delusional about their own kid. He asks for the real story of what happened upstairs. They tell him (minus the rubber) and they all agree that Dylan was a complete jackass and probably deserved a wedgie. Tom gets a call from his big client, who is understanding because he also has a difficult son. Tom agrees to go to a baseball game with the client and their sons. I wonder if we are going to see this play out or if Tom just gets to leave the room with a comment about getting an unlisted number.
Carrie tells Larissa that she can't write the piece because she actually likes Weaver. Larissa says she just gave up a career opportunity for a boy, and the world is full of boys. Carrie says she has a lot of ideas but Larissa asks her to make her a cappuccino. Carrie doesn't care, though, she has a cute and successful boy to kiss.
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