Tangled (2001)

David wakes up in the hospital after he is found injured and stumbling through the woods. The police question him regarding what happened, and whether there were other people involved.  As David tries to piece things together, the movie is told via flashback with recollections of the past several years.

David is in love with fellow student Jenny, who lives next door to  him.  The two spend lots of time together, but David doesn't dare to ask Jenny out or let her know how he feels.  

When his old friend Alan decides to attend the same college, Jenny becomes interested in Alan. Unlike David who's awkward around women, Alan is confident, charming, and has no problem getting women.

David is pissed, which is ridiculous since Alan asked him if he liked her before asking Jenny out. But wimpy old David doesn't even dare to tell his best friend that he likes Jenny.  So angry old David warns Jenny that Alan isn't good boyfriend material because he dumps girls once he's tired of them, and got kicked out of his last college due to his bad boy antics.  Jenny is not amused.

There is no way this can end well for any of our characters. There's a twist ending, and although Alan is an ass, is he really a bigger ass than the guy who doesn't dare ask out the girl of his dreams, and then gets mad when she ends up with someone else? Nah, they're both asses.  Get rid of both of them and find a confident, faithful guy with a spine, Jenny.