The Carrie Diaries loves to get through all the holidays in a season, so since the last episode was right after New Year's Eve, this one is right around Valentine's Day. It rarely has an episode that lands right on a holiday, but it's a good way to show the passage of time. Carrie is happily strolling through the streets of New York, thinking about all the wonders of Valentine's Day (and none of the massacres). Carrie has so many coats, I want to know where they come from and how well that internship pays.
She walks in to Sebastian's new place (which is Larissa's old place) and it's covered in man cave types of things, before man caves were a thing. Oh, how I long for simpler times. Sebastian has littered the place with skateboards and skateboard types of things. Carrie did not know Sebastian was into skateboarding, but look at that hair — it's a given. Sebastian tells Carrie to remember the name "Tony Hawk," because he's going to be huge. Audible exasperated sigh from the audience.
Sebastian wants to start a skate culture brand for gear and apparel. Carrie doesn't know what to make of all this (it's a good idea, though, take it from the future!). Sebastian says "enough about skateboards. Let's talk about Valentine's Day." What planet are we on and how do I get out? He made a reservation for them for dinner and Carrie has high hopes because it needs to be perfect.
Back at high school, where fewer and fewer people go, Maggie has received an acceptance letter to Central Connecticut University. But she doesn't have financial aid. Bleh, Maggie, you're so boring even after your miscarriage. Donna rolls up in a slutty, military-inspired getup to announce that it's military recruitment week. So is this like the fleet week episode of Sex and the City? She directs their attention to the recruiters and it comes to Maggie's attention that Donna and Mouse are friends now. Yes. Everyone should be friends with Donna. She's the best.
At Interview, Larissa goes over some bad modeling shots, Samantha volunteers to model and is quickly denied. Walt comes in, because of this wide-open-door policy that this magazine has, to meet up with Bennett to see the new Woody Allen movie. Samantha doesn't know who Woody Allen is and isn't that quaint. She tells them that for Valentine's Day, they all need to see her at her new place of business: the Heartbreaker party at Boy, the most fabulous gay club in the city. Larissa says the Heartbreaker party is legendary so she is in. Bennett wants to go but it makes Walt nervous. Carrie doesn't want to go because of her gross plans with Sebastian. Lame.