We’ve all made at least one regrettable decision when it comes to picking a date night movie. This post was inspired by the time I watched Blue Valentine with my then-boyfriend — on Valentines Day. There’s nothing like watching the crippling depression of two people who shouldn’t be together trudging on with their lives to make you really feel the love. For those of you looking for actual suggestions, I’ve included a list of legitimate movie recommendations for your Valentines Day weekend — but we all know the bad ones are more fun to think about, right?
Worst Movies to Watch On Valentines Day
Eternal Sunshine of the Spotless Mind: This surreal 2004 experience is a perfect choice — for someone who’s going through a break-up. Don’t make your significant other sit through this, unless you are very secure in where the two of you stand.
500 Days of Summer: Same goes for this one, which I partially credit/blame for a 2010 break-up of my own. It could serve as a good litmus test, though! Who does your significant other side with in the movie, and why?
Fatal Attraction: I’ve never actually seen this movie, but a friend suggested it. Based on the cooked rabbit scene alone, it does seem like a harrowing choice for date night. Tread lightly.
Closer: What a great cast! What a depressing, crushing movie. I like all four actors in this very much, but they all play pretty rotten people. Pick this one if you want someone to suspect that you’re cheating on them.
Knocked Up: This 2007 movie has not aged well, and it’s also probably pretty uncomfortable to watch with someone you are trying to take things further with. (See also, from the same year, Juno — although I hope it’s aged better. Not likely, home skillet.)
Best Movies to Watch On Valentines Day
Away We Go: I think there’s something for everybody in this sweet little movie. As someone who loves to wander, it holds a very special place in my heart. Maya Rudolph is amazing in it, and Dave Eggers wrote the screenplay with his wife.
The Wedding Singer: I have, and may always suffer from, a bizarre soft spot for Adam Sandler. I especially like him with Drew Barrymore, so therefore see also 50 First Dates. I’ve seen both of these more times than I care to admit.
Charade: This Audrey Hepburn/Cary Grant thriller from 1963 is 113 minutes of pure fun. It’s got action; it’s got romance; it’s got Audrey rocking a gorgeous updo even when out-running a cadre of thieves. You can’t go wrong here.
Casablanca: It’s cliche, right? But it’s classic for a reason. Those one-liners, even the ones you already know, are timeless. This movie is where it’s at for Valentines Day. Here’s looking at you, kid.
Waiting for Guffman: This, and other Christopher Guest movies, can serve as a different kind of test, if you’re into making Valentines Day a celebration of undue pressure and playing mind games. But it’ll also let you know pretty quickly what kind of sense of humor your partner’s carting around.
On my first valentine’s day alone, you and I saw 27 Dresses. The next Feb. 14 I went alone to see Away From Her, which is about a wife who gets Alzheimer’s and her husband has to put her in an institution. It was not a good idea.
Going to see 27 Dresses with you is still a fun memory for me even though that was a very sad Valentines Day for our family!
Gary, “Away From Her” is so, so devastating. I’m with you on that one.