The search for the worst date movie of all time.

It's always awkward if Valentine's Day rolls around when you're in the delicate early stages of a romance. A fancy dinner seems too official, so you look to the multiplex or your Netflix queue and plan a low-key movie night to mark the occasion. You try to choose something that will create the proper ambience. Often this means a movie with the familiar love narrative of boy meets girl, boy loses girl, boy gets girl. Most of the films included on best date movie lists— Say Anything, Pretty Woman, Jerry Maguire—follow this comforting, if clichéd, plotline.

Sometimes, however, a seemingly innocuous love story can give you more than you bargained for. Take the new Nicholas Sparks love-fest Dear John. It seems like the perfect second-date choice: Watching wide-eyed Amanda Seyfried and chiseled Channing Tatum cavort would make any heart flutter. But then someone dies, and the vibe goes from sultry to sad-sack. A grizzled couple, months or years into a relationship, can survive this sort of thing. A fragile new love might have more trouble weathering an unexpectedly weepy evening.

How can you know when a movie might stunt the growth of a young romance? At first blush, the hallmarks of a terrible date movie might seem rather obvious. Such a movie might feature multiple instances of projectile vomiting, like the Sam Raimi horror flick Drag Me to Hell. It might graphically depict genital mutilation (and cause the audience to projectile vomit), like Lars Von Trier's Antichrist. Or it might involve aliens emerging from human rectums, as in Dreamcatcher, a movie a Slate colleague was taken to on a first date. (The relationship, miraculously, survived.) But these movies wear their unsuitability on their sleeves. You know exactly what sort of bizarro dystopian nightmare you're getting into when you purchase a ticket to a Lars Von Trier movie—if your date walks out of the film, and your life, you've got no one but yourself to blame.

There might even be a case to be made that a movie like Antichrist is a good bet for a date. It's probably not going to get you any nooky, but a shocking, divisive movie like Von Trier's can often act as a useful litmus test. Maybe you don't want to date someone who can't stomach the occasional on-screen log to the groin in the name of avant-garde cinema. One Slatewriter brought a prospective beau to see the morbidly erotic In the Realm of the Senses, which also involves genital mutilation and which happens to be one of her favorite movies. She never heard from him again. "Just as well, since anyone who can't roll with Realm O' isn't my type anyway," she said.

Even if it isn't a litmus test, per se, a controversial movie can still be a fruitful choice in the first few outings. I saw the documentary Capturing the Friedmanson a third date. Through a combination of interviews and home-video footage, it tells the story of a Long Island father and son who are convicted of multiple counts of child molestation. Did my date and I want to snuggle after seeing it? God, no. Did we have an engaging discussion about family and memory afterwards? We sure did.