Erin (DREW BARRYMORE) is a 31-year-old intern at the New York Sentinel where she hopes one day to work as a real and full-time reporter. Garrett (JUSTIN LONG) works at a New York based record label where he's stuck handling boy bands rather than bringing true talent to the forefront of the music scene. The two meet one night at a bar where he's out drinking with his roommate, Dan (CHARLIE DAY), and their friend, Box (JASON SUDEIKIS), who are consoling him over his recent break-up with his girlfriend.
Garrett and Erin immediately hit it off and, following sleeping together, agree to keep their relationship casual. That's not only because he just got out of one, but also because she's moving back to San Francisco in 6 weeks to live with her sister, Corinne (CHRISTINA APPLEGATE), and her husband, Phil (JIM GAFFIGAN), while finishing her last year of graduate school at Stanford.
Yet, as those weeks pass, the two end up falling in love and decide to continue dating, albeit in a long-distance relationship. But they quickly discover that phone calls, text messages and occasional visits in person are poor substitutes for the real and consistent thing. Throw in the fact that Garrett finds himself jealous of Damon (OLIVER JACKSON-COHEN), the handsome bartender at the restaurant where Erin works, and she becomes suspicious of Garrett's attractive coworker, Brianna (KELLI GARNER), and the couple realizes they're going to have a hard time dating from across the country.