- The book Jesse discusses with Dean in the coffee house and hospital is David Foster Wallace's "Infinite Jest". Wallace committed suicide in 2008. Dean's situation also resembles the college experiences of Wallace, who was hospitalized for depression while trying to complete his senior thesis, a novel, at Amherst College.
- Filmed mostly at Josh Radnor's alma mater Kenyon College, a small liberal arts school located in Gambier, Ohio. Allison Janney was a student there.
- The book that Jesse is reading on his way to the laundromat is "The God of Small Things" by Arundhati Roy.
- Although not mentioned by name, the "vampire book" that sparks an argument between the two main characters is based on "Twilight". Elizabeth Reaser, who plays Ana in this film, also plays Esme Cullen in the "Twilight" movies. In the film, the book's title is "Lunar Moon". Its cover is similar to that of "Twilight".
- There was a storyline with Michael Weston as Miles, a friend of Jesse who is trying to go to Spain but has several issues that keep him from going. All of his scenes were filmed but not in the movie; they are featured in the Bonus section as Deleted Scenes.
- The Soundtrack uses classical music through a discussion after a class Zibby takes. The music used includes: Beethoven's Sixth symphony, 1st movement - Herbert von Karajan with Berliner Philharmoniker Wagner - Overture to Tannhauser Mozart - Cosi fan Tutte aria Vivaldi - Guistino - Vedro con mio diletto (sung by Philippe Jaroussky) Monteverdi - 9th Book of Madrigals "Zefiro Torna" (sung by Philippe Jarrousky and Nuria Rial)
- In the film's opening Radnor's character is reading God of Small Things, whose plot also deals with the 'laws of love', and what happens to those who break these rules - paralleling the characters of the film.
- Elizabeth Oslen's first movie not to be rated R.
- The book discussed in the coffee shop is David Foster Wallace's "The Infinite Jest." Radnors co-star Jason Segal, portrayed Wallace in the film The End of the Tour.
- Zibby: So, what was your major?
Jesse Fisher: I was English, with a minor in history, just to make sure I was fully unemployable.
- Jesse Fisher: I believe in consequences.
Zibby: No, you believe in guilt.
Jesse Fisher: Maybe. But guilt before we act is called morality.
- Zibby: Try not to over-think things, okay?
Jesse Fisher: Ah, you're talking to the wrong guy.
Zibby: Well, look. We connect really well, don't you think?
Jesse Fisher: We do, yeah. I just can't figure out if it's because you're advanced, or because I'm stunted.
Zibby: It's because I'm advanced.
Jesse Fisher: Maybe. But I'm also a little stunted.
- Zibby: How can you hate something if you've never read it? I mean, isn't that like what repressive regimes do? You want to burn books you don't like?
- Zibby: I sometimes feel like I'm looking down on myself. Like there's this older, wiser me watching over this 19-year-old rough draft, who's full of all this potential, but has to live more to catch up with that other self somehow. And, uh, I know I'll get there. It's just sometimes I think I want to rush the process, you know? And I don't know, maybe, um - maybe I thought you were some sort of shortcut. Does that make any sense?
Jesse Fisher: If I wrote you, I would be like, "This is the best rough draft ever."
- Jesse Fisher: I feel different now than I felt when I was here, and I hate to break this to you, but so will you.
Zibby: So you're saying things suck? I should prepare myself for suckiness?
Jesse Fisher: No, a liberal arts education solves all your problems.
Zibby: Thank God!
- Zibby: It doesn't bother me.
Jesse Fisher: Well, it bothers me.
Zibby: Well, it shouldn't. Age is a stupid thing to obsess over. What if reincarnation is real, huh? Think about that, What if I am like thousands of years older than you?
Jesse Fisher: Okay, that's not really a sound argument.
Zibby: Why not?
Jesse Fisher: Because it's like saying what if reality is all an illusion, then there are no consequences to anything, we're completely off the hook... and I believe in consequences.
Zibby: No, you believe in guilt.
Jesse Fisher: Maybe, but guilt before we act is called morality.
- Nat: Do you drink coffee?
Nat: What? That's crazy! So does my friend here. You two, tomorrow. Schhp... coffee.
Zibby: Yeah, I could do that. Are you in too?
Jesse Fisher: Um, I...
[Nat gives him a boost]
Jesse Fisher: Uh, yeah, that'd be... that's great. Nine o'clock okay?
Zibby: [laughs, then realizes] Oh, you're serious? Is, uh, 11:30 okay...?
Jesse Fisher: Uh, yeah... yeah, that works...
The majority of scenes were filmed at Kenyon College in Gambier, Ohio. Kenyon is the real-life alma mater of both Radnor and co-star Allison Janney.
The film premiered at the 2012 Sundance Film Festival in January 2012.