Vague movie question?

I thought this movie had Paul Rudd in it, but it apparently doesn't after checkng imdb.com. I'm pretty sure the guy has black or brown hair and I was thinking the girl may have been mandy moore... pretty sure it's not though, got this movie stuck in my head though. it's a romantic comedy and all I can remember is something about the guy walking up to the girl and him crossing like a sidewalk or a street to get to her and there being a tree in the background and maybe but not sure that the premise is that a guy falls in love with a woman whose daughter likes the guy too. please help!