The Man in the Moon (1991) directed by Robert Mulligan (not to be confused with Man on the Moon, starring Jim Carrey about the life of Andy Kaufman - also a great flick but this isn't the one I'm referencing here).
The Man in the Moon was Reese Witherspoon's first movie and at 14 years old she originally went to audition as an extra but ending up getting cast as the lead! I was just flipping through the channels when I stumbled upon it and had no idea what it was about. I only read the caption that the digital cable service provides which read something like, "small town girl dealing with her first love and heartache". I thought oh well, let's see what this is about and worst case, I'll fall asleep and catch up on some much needed zzz's. Well I was definitely surprsied by this film. It's simple and heart warming and, draws on a few other emotions that sort of sneak up on you.
I won't say much more for those of you who would want to see it other than after I watched it, I had to look it up on imdb and discovered that this film was based on a true story.
Here's a link on amazon for those of you who are interested but I recommend just seeing it without reading too much into it. And yes, it's primarily a chick flick but some sensitive men out there will enjoy it too.