Entertainment
The Worst First Dates In Movie History
Universal Pictures
I go to the movies to escape from real life, but also to see my own reflected back at me. And I don't think I ever feel more connected to a movie character than when he or she is enduring one nightmare of a first date. Everyone has them. You don't know if you click with someone until you try, and that adventurousness can result in some seriously awkward evenings. Of course, in some of the movies on this list, the circumstances are what I'd call extenuating: family schemes, body-switching, time travel, and sociopathic murderers, just to name a few bumps in the road. But bumbling Hollywood romances makes me feel better about myself and I hope they do the same for you. So keep clicking through to see the 33 worst first dates in movie history.
I should point out that many of the relationships in this gallery actually work out in the end. An uncomfortable start doesn't necessarily indicate a complete mismatch. Sometimes it's a confidence thing or a warning sign for friends being way too involved. And sometimes a really disastrous date is a sign to run away as fast as you can and never look back. Here's to all those characters who put themselves out there, even when their attempts turn out like this.
1. '13 Going On 30'
This is only a first date because 13-year-old Jenna Rink has recently woken up in her adult body. And though she looks like Jennifer Garner, this innocent teen is by no means prepared for her pro hockey player boyfriend's ice-themed striptease.
2. 'You've Got Mail'
It's retail book heir Joe Fox who first discovers that the woman with whom he's been chatting online is his local bookshop rival, Kathleen Kelly. Thrown, he uses their blind date to mock Kathleen getting stood up. Not his best moment.
3. 'There's Something About Mary'
It becomes painfully obvious in this flashback why Ted wants another shot with the beautiful Mary. There was an incident with a fly zipper back in high school that sent that poor guy to the emergency room.
4. 'When Harry Met Sally'
Harry and Sally attempt to set each other up with their best friends. But destiny tells the foursome that they've got it all wrong. Marie and Jess pair up instead, leaving the titular couple to figure out what's really going on between them.
5. 'Back To The Future'
Ah, the Oedipal nightmare of going to the Enchantment Under The Sea dance with one's own mother.
6. 'Clueless'
Disillusioned by high school boys in saggy pants, Cher is enchanted by the James Dean daydream new kid, Christian. It takes her a while to realize that their first date wasn't a first date to him, but he's still welcomed into the crew as her new art appreciation tutor and shopping buddy.
7. 'Gone Girl'
Desi Collings thinks he's reuniting with his ex-girlfriend Amy Dunn, but the opportunistic, shrewd, and remorseless Amy is just using his infatuation with her to further her plan of framing her own husband for her murder. When she's finished with him, she finishes him.
8. 'The 40-Year-Old Virgin'
Trish might be the one for late bloomer Andy, but they can't consummate their relationship if her daughter keeps walking in on them.
9. 'Rushmore'
Max Fischer — egotistical and obsessed with a teacher at his boarding school — spends an evening out ridiculing her aw-shucks new boyfriend.
10. 'American Pie'
It has a satisfying ending for everyone involved, but Jim's prom date with band geek Michelle starts off with some graphic insight into the sexual appetite of the school's musicians.
11. 'Sleepless In Seattle'
Sam wants to get back out there after grieving his wife's death, but his son has a very specific pen pal in mind to be his new mom. Hence, he does everything he can to sabotage his dad's dates with an overbearing decorator.
12. 'Pulp Fiction'
"Entertaining" your boss's wife is a precarious situation. Vincent and Mia come through during the twist contest, but the night takes a turn when Mia overdoses on heroin and takes an adrenaline needle to the chest.
13. 'Bridget Jones's Diary'
It's all domestic sweetness when Mark Darcy shows up unexpectedly to Bridget's birthday dinner. But the night spirals into chaos when he and nemesis Daniel Cleaver have a rather uncoordinated fight in the street and the dining room of a nearby Greek restaurant.
14. 'Return To Me'
Being rude to the waitstaff is a dealbreaker. When widower Bob is set up with one of his best friend's clients, he's more interested in the lovely waitress than the nasty woman berating her.
15. 'Something New'
Kenya doesn't think that Brian is her type. But after stranding her blind date at a coffeeshop, she hires him to landscape her backyard and learns a little something about keeping her heart open.
16. 'Look Who's Talking'
In love with his boss Mollie, her nanny James gives her dates ruthlessly bad advice about how to woo her.
17. 'Grease'
When the date starts with "shimmying down the drain pipe," you know you're in for a classy evening. At least Rizzo's pregnancy scare was just that.
18. 'It Follows'
This might be it: the worst first date of them all. After Jaime and her boyfriend do the deed in his car, she wakes up to find that she's now cursed with a relentless demonic presence that will follow her wherever she goes.
19. 'American Psycho'
Patrick Bateman has nice abs and a great apartment, but most of his first dates turn into blood baths.
20. 'Scott Pilgrim V. The World'
In this allegory for getting the hell over your date's sexual history, Scott Pilgrim has to battle all of his love's "evil exes" in order to win her heart.
21. 'The Wedding Singer'
Robbie Hart knows very well that he's in love with the engaged Julia, so he should have never accepted a date with her Madonna-obsessed cousin, Holly. Though, it doesn't take Holly long to suss out why Robbie is so withdrawn.
22. 'Blind Date'
It's a terrible date that runs the course of a whole movie. Bruce Willis and Kim Basinger star in a comedy about a woman who gets a little crazy after a few drinks and the guy who's pulled along for the ride.
23. 'Taxi Driver'
Disturbed insomniac Travis Bickle takes a respectable date to see a pornographic Swedish film and can't comprehend why she's so grossed out.
24. 'Forgetting Sarah Marshall'
Peter and Rachel's relationship starts out as a ruse to make Peter's famous ex-girlfriend jealous, but starts to turn the corner right around the time Peter sings a ballad from his vampire puppet musical for her.
25. 'Pride & Prejudice'
Her mother is hoping their new neighbors will be lucrative marriage prospects for her older daughters, but Miss Elizabeth's first experience with the serious Mr. Darcy is overhearing him disparage her beauty at a local dance. It's not you, girl. It's him.
26. 'Deliver Us From Eva'
Her family hires Ray to keep Eva busy and away from their business, but Ray eventually falls for the "difficult" woman. Because difficult women are awesome.
27. 'Hitch'
Those who teach can't always do. Relationship expert Hitch has a truly tragic first date with the beautiful Sara, going so far as to accidentally kick his companion in the face.
28. 'Crazy Stupid Love'
Jacob the player coaches long-married Cal to get back on the dating horse. But his first "conquest" is too much woman for him...and also happens to be his son's teacher, a fact that will come back to bite him later in the movie.
29. 'Never Been Kissed'
Josie is the victim of a cruel high school prank. The class heartthrob asks her to the prom, only to egg her as he and his friends drive by her house laughing. Fortunately, her job as an investigative reporter gives Josie another chance at that social scene.
30. 'Knocked Up'
Ben thinks that Alison asked him out to continue whatever it was they started when they drunkenly hooked up a few weeks previous. But Alison has some news for him, and it changes both of their lives forever. ("With a baby?")
31. 'As Good As It Gets'
Brutal honesty can be a desirable quality in a mate. (You always know where you stand.) But it takes some getting used to, as you can see from Carol's first date with the curmudgeonly Melvin in the Oscar-winning comedy As Good As It Gets.
32. 'I Love You, Phillip Morris'
Based on a true story, I Love You, Phillip Morris tells the story of an unexpected rollercoaster of a love affair. But I'm sure there are better locations for a first date than federal prison.
33. 'Silver Linings Playbook'
Neither of them probably consider this late-night diner trip a date. In fact, Pat orders Raisin Bran to make that specific distinction. But Pat and Tiffany learn a lot about each other when Tiffany unleashes her frustration over being pegged as a promiscuous, unstable girl. And that honesty leads to their eventual coupling.
