She's Out of My League (2010)

Name: She's Out of My League
Released: 2010

When he starts dating drop-dead gorgeous Molly, insecure airport security agent Kirk can't believe it. As his friends and family share their doubts about the relationship lasting, Kirk does everything he can to avoid losing Molly forever.

Genres: Romance, Comedy

What to watch after She's Out of My League

Fanboys (2009) — Jay Baruchel appears in both
She's All That (1999) — Same subject: group of friends
Fever Pitch (2005) — Same subject: dating, group of friends
She's the Man (2006)
Just One of the Guys (1985)
What's Your Number? (2011) — Same feel: feel-good, fun