Not that I've ever gone on a date night to the movies (have to have a date to go on a date), but one of my favorite "romantic" type films (of which I don't like many) is "The Holiday". I LOVE this movie, and while it does happen around Christmas time, it's a movie worth watching year round. The four main characters are so adorable that you can't help but love the movie.
Kate Winslet's character being my favorite, I feel a connection to the character - I understand her. Even though our life experiences are no where near alike a lot of her personality I see in my own. Cameron Diaz is pleasant in the film as well, and I'm not a fan of hers (find her a tad overrated), her character is a sympathetic one from the onset when we meet her douchebag of an ex-boyfriend. Jude Law and Jack Black as the ladies' unexpected love interests make the movie sing.
And I'm not a fan girl of either of them, though if they played characters like the ones they have in this movie all the time I probably would. This movie proves there are good guys out there, you just have to be willing to see past the "good friend" stage.
Eli Wallach (RIP!) is also the charming neighbor that Kate's character befriends. He brings a charm and warmth that the movie thrives on. You can't not love him. It's a beautiful friendship. I need an "Arthur" in my life.