Aliana Thompson | Contributing Illustrator

Watching a movie on your first date? Bold choice. I have faith in you, though. You can make it work. All you have to do is pick a good movie — one that’s engaging, sets a good mood, and sparks good conversation so you can get to know the person you’re sitting next to.

Your date says they know a good movie. The Rotten Tomatoes score agrees with them. It seems like a good pick, so sure, why not put that one on? What’s the worst that could happen? Well, you could ruin the date, for one. There are tons of acclaimed movies out there, but not all of them translate well to a first date. This list is a compilation of 10 such movies, each excellent and well worth your time, but awful to watch with someone you just met. Without further ado, here’s to your awful first date, and here’s hoping your date never puts one of these on.

1. “2001: A Space Odyssey” (1968)

There’s a lot to love about “2001.” The soundtrack is iconic, the sci-fi visuals are stunning even after nearly 60 years, and the supercomputer AI antagonist HAL 9000 is delightfully sinister and increasingly relevant in a ChatGPT-riddled world. Unfortunately for you, the movie sports a hefty two-and-a-half-hour runtime, and you can feel it. Get hyped for minutes-long sequences of characters silently drifting through space, advancing the inscrutable plot at a snail’s pace! Thank God for your film-bro date, though, who’s pausing the movie every five minutes to tell you how they filmed that scene. 

2. “Doubt” (2008) 

I have genuinely no idea how your date convinced you to watch this one. Philip Seymour Hoffman plays a priest at a Catholic grade school, who may or may not be a pedophile (hence “Doubt”), opposite Meryl Streep, who plays the strict head nun who’s trying to take him down. This movie is chock-full of stunning acting performances and thought-provoking themes, but the prevailing emotion incited by the film is anxiety, which might not be how you want to feel on a first date. Just a thought.  

3. “La La Land” (2016) 

At first glance, “La La Land” feels like a great pick. It’s funny, energetic, and the first act features a sweeping romance between characters played by Ryan Gosling and Emma Stone. Who doesn’t love them? But as the movie carries on and their relationship starts to crumble, you might start to feel worse about your pick. The two characters are fundamentally incompatible, but they never get over each other. Definitely the sort of stuff you want to be thinking about while starting a relationship.

4. “Misery” (1990) 

Horror movies are risky on a first date, but they can work. “Eek,” you can say, before clinging to your date in the dark. Romantic! But “Misery” is an odd pick. This movie follows the story of an author (James Caan) who’s rescued from a blizzard-induced car wreck by his number-one fan (Kathy Bates), who begins nursing him and his broken legs back to health. When she finds out he’s killed off her favorite character in a new book, however, she forces him to rewrite the ending. Bates’ performance is both outstanding and nightmarish, and Caan’s character’s lack of mobility makes the film a painfully tense watch. The movie is just specific enough to begin raising some questions about your date. And if they picked this, then I’m terribly sorry to inform you, but they are, in fact, a serial killer. 

Aliana Thompson | Contributing Illustrator

5. “Moneyball” (2011) 

Really? You picked “Moneyball”? Kiss notions like “important female characters” goodbye in this baseball movie. Most of the action in this film takes place in the dingy conference rooms and offices of the Oakland A’s aging stadium as characters Billy Beane (Brad Pitt) and Peter Brand (Jonah Hill) fight to take the soul out of baseball scouting and replace it with raw statistics. As you might imagine, the Oakland A’s are a total boy’s club. Billy Beane is supremely divorced, and the only female characters are his ex-wife and child, who are on screen for five minutes tops. Not the most relatable choice for women on a first date. Unfortunately, the guy who put this on was right. It’s great. It’s a refreshing take on the tired genre of sports movies, and the dialogue is smart and snappily written. Have fun picking desiccated Zyns out of your couch cushions when this guy leaves, though. 

6. “Past Lives” (2023) 

Want to get into uncomfortably deep conversations on your first date? Watch “Past Lives.” This movie centers on the question of “what could have been?” as it follows Nora (Greta Lee) as she reconnects with a childhood love, Hae Sung (Teo Yoo), from before she moved from Korea to New York. The only holdup is that Nora is already married to a guy in the U.S. “Past Lives” is subtle, moving, and well worth a watch. In terms of your first date, however, the main conversation this movie invites is talking about past relationships, which sure doesn’t seem like the best way to start this one. 

Aliana Thompson | Contributing Illustrator

7. “Call Me by Your Name” (2017) 

This is a baffling pick. Don’t get me wrong, this movie is gorgeous — perhaps even aesthetically perfect. The Italian countryside glimmers, and the color grading lends the film a hazy, nostalgic glow. The Sufjan Stevens-heavy soundtrack is another standout (seriously, if a failed first date has you torn up, go cry to those songs sometime). Where this movie enters bad first date territory is in its main romance between gangly 17-year-old Elio (Timothée Chalamet) and full-grown man Oliver (Armie Hammer), a 24-year-old graduate student studying Greco-Roman history. Chalamet is alarmingly young-looking, and Hammer looks like he could be 30. The emotion one feels when looking at them is, quite frankly, panic. The movie does not expend much energy dissecting this power imbalance, and even if it did, I’m not sure you’d want to watch it on a first date. 

8. “Marriage Story” (2019) 

What did you expect? It’s about a messy divorce. The movie is an absolute acting tour de force from both Scarlett Johansson and Adam Driver. The screenplay handles the topic deftly, and the characters feel painfully believable. That being said, how on earth did your date convince you to watch this? What was the pitch? Maybe the date was doomed from the start. 

9. “Labyrinth” (1986) 

It’s Jim Henson! The “Muppets” guy! This movie is an incredible feat of creativity. The puppets are fantastic. The visuals are surreal and breathtaking. David Bowie is smoking hot as Jareth (the goblin king), and his campy performance and oppressively ’80s hairstyle are second to none. On the other hand, this movie does not get nearly enough credit for how unnerving it is. The puppets range from eerie to downright terrifying (looking at you, hand tunnel). Worst for your little tryst, though, the puppets are deeply unsexy. Whatever mood you had, it’s surely not going to survive Hoggle, the uncomfortably detailed troll, or the horrifying Fireys, the bird-like creatures with detachable limbs.  

Aliana Thompson | Contributing Illustrator

10. “Juno” (2007)

“Juno” is 99% of the way to a perfect first date movie. It’s romantic, it’s comedic, it’s, well, a rom-com — and a nearly perfect one. The story is heartfelt and witty, the pacing is excellent, and the exploration of teenage pregnancy functions perfectly in the film. Oops! Yeah, this is a teen pregnancy movie. Lots to chew on for a first date! At least it’ll get you thinking about safe sex, if that’s miraculously still where the date is headed.