You've Got Mail
The quintessential online dating movie, this one dates back all the way to 1998 and is a remake of The Shop Around the Corner. Kathleen Kelly (Meg Ryan) and Joe Fox (Tom Hanks) meet in an AOL chat room, and the rest is history. If you're looking for an easy, breezy, and sweet romantic comedy, then check this one out immediately.
Lesson Learned: Don't judge a book by its cover — or reputation!