She's Out of My League (2010)

  I disagree with the tagline here because I didn't think The Hangover was particularly funny.  She's Out of My League, however, turned out to be much better than the pile of steaming shit I was sure it was going to be, approaching good even.

TSA flunky Kirk (Jay Baruchel) is stunned when a beautiful girl (Alice Eve) shows interest in him, as are all his friends and family.  Convinced he does not deserve her, Kirk grows more and more anxious as the relationship progresses, waiting for the other shoe to drop.  This has the effect of sabotaging every interaction he has with her, creating a self-fulfilling prophecy of doom.

As stupid and unnecessarily vulgar as this movie is, it's the first time I've ever seen this issue addressed.  I think all of us know of at least one friend who is so much more than they give themselves credit for being and if you don't, it's you.  I'm going to quote from another movie (faux pas, I know) and say that "we accept the love we think we deserve" and for most of us, that's a huge disservice.

If some hottie strikes up a conversation with you, don't immediately assume you are being punk'd, or that he/she has had a recent head injury.  Go with it!  If it happens more than once, maybe reevaluate your self-opinion.  And if your friends and family ever say something like so-and-so could do better than you, dump their toxic asses.  You don't need that in your life.