Ten Worst Date Movies Of All Time


Sugar and spice and everything we both want each other dead. Image via New York Daily News

Taking somebody out on a date to the movies is a tradition as old as love itself. Or, I guess whenever the first Nickelodeon opened up.

Gone Girl is still on my mind, and it will be for some time. This twisted tale of toxic love would probably make an awkward date movie [Full disclosure: I did not see this on the date]. People have even written about this in depth.

This inspired me to go back and think about movies that could ruin a budding romance. These movies might make you feel uncomfortable, or, you know, doubting that any relationship could ever work. Here is a list of the the ten worst movies to ever watch on a date.

Note: These are not bad movies (okay, one of them is), they just aren’t ideal to watch on a date. Also, some minor spoilers ahead.

(500) Days of Summer

Oh, so you’re taking a girl out you met on OK Cupid because you found out that you both like Arrested Development? Well, just get ready to hear Chloe Moretz say, “just because somebody likes the same bizarro crap you do…that doesn’t mean they’re your soulmate.”

Before Midnight

Okay, so the first two chapters of this trilogy are about two attractive people walking the streets of Europe and falling in love. Get ready for the final installment, in which the two of them spend 45 minutes screaming at each other. Hey everyone, marriage is hard! Love isn’t a fairytale! Shrek lied to us all!

Blue Valentine

Hey, Ryan Gosling and Michelle Williams are two beautiful people. Let’s see them finally get together. Great! Now, let’s watch their marriage completely fall apart in the most depressing way possible. Love is a lie!

Boogie Nights

Mark Wahlberg’s fake dong sets unrealistic expectations for men.

Eyes Wide Shut

Creepy masked orgy? Check. Awkward sexual chemistry? Check. Suggested child molestation? Check. Stanley Kubrick never made films that were meant to make anybody feel comfortable, but Eyes Wide Shut takes it to another level. “Well that was…a thing” is probably the highest compliment you could pay it.


This is a movie you shouldn’t watch under any circumstance, but listening to Jennifer Lopez say “gobble gobble” is more than enough to kill the mood.

The Graduate

If you have just stormed into a wedding and “rescued” the girl of your dreams from her possible marriage to some blonde jock, you two should not watch this together. The ending is sad, bozos.


A man falls in love with his computer. First, this seems to send the message that any relationship, no matter how unusual, can work. Then, you start to realize that this couple is doomed because they are in two very different places in their lives. Moral of the story: take a moment to appreciate Siri; typos and all. Just don’t fall in love with her.

Match Point

Recent allegations against Woody Allen are probably a big enough buzzkill on their own. But one of his darkest dramas sees a man cheating on his wife, and then plotting to kill his goombah (am I allowed to use this word?).


Lars von Trier is another filmmaker who strives to make his audience feel as uncomfortable as possible. Nymphomaniac would probably be a good litmus test for how much your significant other really wants to be around you. If the penis montage doesn’t do it for you, then just wait until you see what weird fetishes are displayed in the second half of this two part sexual odyssey.