Oscar remembers his past and wonders why he is still a loser. That is until he meets the woman of his dreams.

That is closer but if he has to convince himself she is the woman of his dreams she probably isn't, I would word that different.

I really appreciate the assistance Gentlemen.

How about this one?

During the course of his routine loser life, Oscar, meets the woman of his dreams, and must convince himself and his friends that she's the one.

This is more of a "tagline", which is an advertising tool. A "logline" sums up the concept in 30 words or less, and should contain a protagonist, a specific antagonist, the goals, the obstacles, the "hook", the stakes, some irony, and an idea of the genre.

Geno Scala (sharkeatingman) judge...