Felicity waits outside her advisor's office as Sarah McLachlan sings "Angel" on the soundtrack. Once inside, she tells her advisor all the reasons why she wants to leave New York and go back to Stanford -- for instance, that it's expensive to stay, and that it would make her father happy. The advisor silently appraises her. She mentions that her parents are coming out on Sunday, which seems like good timing. She gets a little choked up as she says that she's going to go back to Palo Alto and become a doctor, and maybe save someone else's life. She gets up to leave and thanks the still-silent-and- rapidly-becoming-creepy advisor for his patience, and comments that he must think she's "a real basket case." He finally speaks to tell her that he looked at her portfolio, and that he's not saying that she wouldn't "make an excellent physician," but she's "already an artist." Felicity looks disturbed and thanks him. He just stares at her some more. She leaves.
Ben knocks on Felicity's open dorm room door; clearly, she learned nothing from the Knoll-nightie incident. He hands her a package that was outside her door, commenting that it must've been put in the wrong mailbox. Felicity opens it and pulls out a cassette tape. Ben asks who it's from. Felicity replies that it's from her French tutor, who was supposed to be married, but three months before her wedding, her fiancé was killed when a jeep hit the motorcycle he was driving. Felicity says Sally "couldn't deal," so she moved away. Felicity could never talk to anyone like she talked to Sally, so instead of writing, she talks to her, and Sally talks back. She says that Ben must have felt the same thing with Jonathan (his dead older brother). Ben says he needs to talk to her. Felicity apologizes for the other night. Ben suggests that maybe they could go up on the roof or something. He adds a "please" and Felicity grabs her coat. Aw, it's Ben and Felicity's first rooftop discussion. There are so many historic moments in this episode.
On the roof, Ben says he wants to tell her the truth, and the fact is that he never had a brother. He had to write something, so that's what he wrote. He doesn't know why he wanted to tell her, but it must be because she provokes him and makes him think about things that he never thinks about. She does all this without even saying anything, but just by the way she looks at him. He says that the "absolute truth" is that the reason he wanted to come to New York was that "it was a pretty good chance to get as far away from everything as possible. My parents, my family, all that crap. And yeah, on top of it, I lied to get in. So, basically, I'm a shallow loser." He's also sorry that he's not the guy she thought he was. She came so far to get to know him, because she thought he was so great, and he's not. He asks what she's thinking. She says she's never made "a substantial choice" in her life, and that's why she came. She thought it was him, but he's "just the excuse." She smiles and says that when she came up to him at graduation, it was "like a high, like a drug," because she had never done something like that before. She says she means that she wasn't sober, and so the first big decision she made turned out to be "just stupid and embarrassing" and something she'll look back on with regret. She shrugs and says, "And that's that." Ben says he wanted to make sure everything is okay with them, especially if she's leaving. Felicity says he didn't have to do that, and Ben says that he did. They both look out over the city. Ben comments that he can't wait to see what the city looks like when it snows.