5. 50 First Dates. An infamous playboy falls for a lady with short-term memory loss. It is up to him each day to prove himself and try creating a lasting relationship.4. Notting Hill. A world famous actress and neighborhood nobody fall for one another after they literally run into one another in the street, and from here there two very different lives continue to collide. 3. How to Lose a Guy in 10 Days. An advertising executive places a bet he can make a woman fall in love with him in 10 days. Que a magazine editor looking to demonstrate how to make a man fall out of love in 10 days, neither knowing the others' motives upon starting to date. 2. Hitch. Will Smith works as a private dating consultant, eventually running into a potential match for himself that ends up being a gossip columnist in search of this 'private dating consultant.' 1. Love Actually. This holiday favorite follows the love lives of several different characters. Watch as they find ways to reveal their feelings to their secret crushes.