Honey (it got terrible reviews, WHY?)
I LOVE THAT MOVIE UGHHHH I don't even know why I love it so much but I DO.
Serendipity. Because John Cusack with a Jeremy Piven kicker? Yes please.
Did anybody mention The Princess Diaries? It's cheesy but I love it. NOTHING like the book(s) though WOW.
A Life Less Ordinary, young Ewan McGregor... a little unconventional but I really liked it.
Wimbledon. I adore Paul Bettany.
I also have to ditto the Sleepless in Seattle and You've Got Mail suggestions. I love the former as a classic, but sometimes I feel like I think the latter is a better movie. So much of both movies are my life though. Nora Ephron in general... my life.
Speaking of Meg Ryan,
I.Q.
About A Boy is my fave of the Nick Hornby-based movies, but there's a healthy dose of drama in it, so I hesitate to put it down as a chick flick... but I still recommend it. Maybe not if you're already feeling depressed because it's pretty heavy at times.