1. Closer (2004)
Why you’ll feel lucky to be single: Apparently, people love cheating. They cheat when they’re in love, and they cheat when they’re falling out of love, and they just cheat, cheat, cheat. People are terrible, basically.
2. Eternal Sunshine of the Spotless Mind (2004)
Why you’ll feel lucky to be single: Are we all just doomed to keep repeating the same relationship mistakes? Are relationships so painful that we need to actually erase their memories away? I don’t know, but sweet sassy molassey, I’m weeping.
3. Waiting to Exhale (1995)
Why you’ll feel lucky to be single: Someone fetch me my fainting couch. This movie is so triumphant in its message of women being the most powerful thing in the universe that it’s dizzying. Basically, men are just there, and women need to stand together. Watch this with a bunch of your friends, and bring plenty of snacks. It’s a doozy.
4. Cruel Intentions (1999)
Why you’ll feel lucky to be single: At least when you’re single, you won’t have a sadistic stepbrother and sister betting on who can destroy your life first.
5. Love Actually (2003)
Why you’ll feel lucky to be single: Even though this is technically a romantic movie, it’s actually super depressing. What love actually is turns out to be a kid in a long-distance relationship, a couple who cannot speak the same language, a married couple on the brink of divorce, and a pair of newlyweds whose BFF is trying to ruin everything. Love is horrifying, actually.
6. Revolutionary Road (2008)
Why you’ll feel lucky to be single: I don’t know why Kate Winslet is in so many movies where love is terrible, but she just is. Just because you’re married, doesn’t mean you’ll be happy, in general.
7. Fatal Attraction (1987)
Why you’ll feel lucky to be single: If you’re in a relationship, chances are that woman you’re messing with on the side will kill your pet rabbit, stalk your family, and try to murder you all. Watch this with some red wine and hide all the knives.
8. Waitress (2007)
Why you’ll feel lucky to be single: Men don’t solve your problems. Only you, and your delicious pies, can solve your own problems. The basic gist of this movie is that while men are often a nice distraction, eventually, you’ll have to do you, and that is great.
9. Chasing Amy (1997)
Why you’ll feel lucky to be single: Aside from the obvious issue of this movie assuming that you can change someone’s sexual orientation, the moral of the story is of course you cannot change someone’s sexual orientation. And trying to do so will basically leave you a shell of a person.
10. (500) Days of Summer (2009)
Why you’ll feel lucky to be single: To quote Tom’s little sister, Rachel (Chloë Grace Moretz): “Just because she likes the same bizarro crap you do doesn’t mean she’s your soulmate.”
11. An Education (2009)
Why you’ll feel lucky to be single: “People lead secret lives and will probably try to ruin yours” is basically the message of this film.
12. Obsessed (2009)
Why you’ll feel lucky to be single: This is basically the Beyoncé and Idris Elba version of Fatal Attraction, and it is filled with delicious amounts of crazy. All of which will make you happy to not be married, or in a relationship with your married co-worker.
13. Unfaithful (2002)
Why you’ll feel lucky to be single: Well, I suppose the argument could be made that if you’re married, you can have an affair with a hot Parisian dude. But to that, I’d say, “Maybe that hot Parisian dude will end up dead.”
14. Once (2006)
Why you’ll feel lucky to be single: Oh, unrequited love. You think you’ll get lucky with a one-night stand, and then, next thing you know, you’ve bought a girl a piano and you’re flying off to London to try and get back together with your ex. Love’s a bitch.
15. American Beauty (1999)
Why you’ll feel lucky to be single: Oh, boy. Well, here’s the problem with white picket fences: The paint will eventually crack. In this case, we have a cheating wife, a lusting husband, a daughter who falls in love with a boy who loves plastic bags, and a 16-year-old cheerleader who’s a closeted virgin. Yep, you’ll be happy to be single after this one.
16. Blue Valentine (2010)
Why you’ll feel lucky to be single: Nothing will make you happier to not be in a dysfunctional relationship than watching the marriage between Cindy (Michelle Williams) and Dean (Ryan Gosling) disintegrate. Watch this movie with tissues and watch it alone.
17. Not Without My Daughter (1991)
Why you’ll feel lucky to be single: You think you know your husband. You really do. But the truth is that you really don’t know a person until they take you and your daughter to Iran and then try to kidnap you both.
18. Fear (1996)
Why you’ll feel lucky to be single: What happens when you meet a cute dude at a rave, then let him fingerbang you on a roller coaster? Well, basically, he goes psycho and carves your name into his chest. Nicole 4 Eva.
19. The Twilight Saga (2008–2012)
Why you’ll feel lucky to be single: Hear me out before you light the torches and sharpen the pitchforks… This series is basically saying that you have to abandon who you are to be in a relationship. And that will make you happy to be you, and not be with a vampire, regardless of how hot and shiny he may be.
20. Thelma & Louise (1991)
Why you’ll feel lucky to be single: Basically, when you get married, you’ll eventually develop an itch to go on a road trip with your BFF. Once you’re on that trip, some truly terrible things will happen that lead you to return to what is essentially a single life again. Everything comes full circle, and you cannot escape the lure of the single-ladies-on-the-run life.
21. Brokeback Mountain (2005)
Why you’ll feel lucky to be single: Jack (Jake Gyllenhaal) and Ennis (Heath Ledger) boned, and life was a cowboy yippee-ki-yi-yay time. Then, they got married to two nice ladies, and everything went to hell. See where I’m going with this?