A shy female college student falls for high school boy who cuts her grass. Goes on many dates before she breaks it off and moves on. Her uptight roommate does not support her relationship with said boy. The main girls roommate goes away for a period (possibly backpacking) and comes back a happier and more care free person

Love That Boy (http://www.imdb.com/title/tt0328078/) ?

That's it! My god, you're a saviour. Thank you thank you thank you.

Glad to help :)