Just about everyone else has been debating the best and worst movies to watch on Valentine's Day. The answers are not as obvious as they seem. So if you're in that situation -- if you're planning, say, your first Valentine's Day with someone, and it's going to be a movie-watching affair -- here is my advice:
Avoid a "classic" romantic comedy and watch something you love instead.
My wife and I met in January of 2000, at the most romantic place on Earth: Syracuse's Erie Boulevard Bowling Center. We hit it off instantly, but I lived in Upstate New York and she lived in Rhode Island. A Valentine's Day together a few weeks later did not seem in the cards -- but then she surprised me with an unplanned February 14th visit. It was fantastic. At a loss for what to do we decided to watch "Annie Hall" -- then and now, one of my all-time favorite movies.
Conventional wisdom might tell you this is a bad choice for Valentine's Day; "Annie Hall" is, after all, kind of sad. Alvy Singer and Annie Hall have their romantic moments, but generally, as funny and sweet and knowing as the movie is, you don't walk away giddy with excitement over the possibilities of young love.
But here's the thing: I adored "Annie Hall." That movie meant something to me. Thankfully, my (future) wife got it and liked it too. We connected over the movie and it brought us closer together. And we're still together 13 years later (side note: holy shit, I'm old).
So that's what I recommend: find something you're passionate about and share it. If your significant other gets the movies you love, odds are they'll get you too. Obviously there are exceptions; if you're really passionate about "The Human Centipede" you might want to table that conversation until February 15th. But within reason, bring something personal and meaningful; that's always better than generic and predictable. If the person you show it to hates it, you might not have the happiest of Valentine's Days. But you'll learn something about your significant other and your relationship. If they love it, then you're made in the shade.
Have a happy Valentine's Day, whatever you do. My wife and I are just taking it easy this year; just some takeout and a movie. I'll let you guess what we're going to watch.