Roses, wine, romance…love is in the airas Valentine’s Day draws near. It’s the perfect excuse for a special date night with that special someone. Speaking of dates, the idea of going on one with somebody new can be exciting but also a bit scary. Even the most confident individuals may be nervous as they get ready to meet a potential partner. Will there be enough to talk about? Is there food in the teeth? Who will pay?
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So many films feature first dates that are seamless and superb, but in some instances (in real life and on-screen), the event can be downright disastrous. Whether there are zipper issues or uninvited guests joining in on the fun, these movies help viewers realize that even in Hollywood, first dates aren’t always picture-perfect.
1’Clueless' (1995)
Cher Horowitzdating a high school boy? As if! Her mind changes, however, once the new guy arrives. Christian is attentive, well-dressed, and good at dancing. When their first night out ends with Cher (Alicia Silverstone) needing to find another ride home, Christian (Justin Walker) quickly sets up a movie night for the duo.
Cher goes out of her way to prepare for what could be “the big night” for her and her new beau. The red face and burnt cookies don’t stop her, but Christian’s admiration for Tony Curtis might. After a failed attempt at footsie and a roll off the bed instead of a roll in the hay, the two decide they’re better off as friends.
2’Taxi Driver' (1976)
InTaxi Driver, Betsy (Cybill Shepherd) is working hard, volunteering to help Senator Charles Palantine become the next president. A young, disgruntled taxi driver notices her drive, beauty, and intelligence. Travis Bickle (Robert De Niro) works up the courage to ask Betsy out on a date, and both seem pleased with their upcoming get-together.
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After a successful outing to get coffee, Travis brings Betsy to a theater that features pornography. Feeling repulsed, she leaves her suitor in the dust. Deep down, Travis must have realized that it was a bold choice for a second date.
3’There’s Something About Mary' (1988)
There’s something about…prom. The excitement of finding a date, wearing fancy clothes, and dancing the night away is a highlight for many high schoolers. InThere’s Something About Mary, Ted (Ben Stiller) is pumped to be taking his dream date to the big event.
While picking up his gal, Ted gets distractedand forgets to double-check that there’s nothing in his zipper’s path during a quick bathroom break. He ends up going to the hospital instead of the dance and loses touch with Mary (Cameron Diaz) until years later.
4’Along Came Polly' (2004)
When Reuben (Ben Stiller) returns from his honeymoon single, he runs into an old classmate. He’s a bit set in his ways and struggles to find the courage to take risks. Polly (Jennifer Aniston) is carefree and doesn’t mind stepping out of her comfort zone.
When Reuben and Polly begin dating, they have dinner at a Moroccan restaurant. After testing his taste buds, the poor guy reacts to the spice. Luckily, his irritable bowel syndrome isn’t enough to send the relationship down the toilet.
5’The Graduate' (1967)
Usually, when someone is talked into going on a date with a beautiful young lady, it’s not a bad thing. In this case, it makes a complicated situation even more stressful. InThe Graduate, Benjamin (Dustin Hoffman)spends his post-graduation nightsenjoying the company of Mrs. Robinson (Anne Bancroft).
Benjamin takes Mrs. Robinson’s daughter on a date but tries to sabotage the outing with Elaine (Katharine Ross). His attempts to ignore the younger Robinson aren’t enough. He decides driving recklessly might do the trick. Maybe taking her to the strip club will turn her off? This is just the beginning of Ben’s adventures (or misadventures?) with the Robinson family.
6’Back to the Future' (1985)
Dating mom to help her fall in love with dad? Sounds complicated, but in Marty McFly’s (Michael J. Fox) world, it all makes sense. When Marty travels back to 1955, he saves his dad and is nursed back to health by his mom.
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Not knowing Marty is her future offspring, Lorraine (Lea Thompson) asks her son to the school dance. As he struggles to avoid his mother’s advances, Marty helps his parents couple up. He even provides the musical backdrop to their first kiss.
7’Get Out' (2017)
Nerves are always present when meeting the significant other’s relatives for the first time. InGet Out, Chris Washington (Daniel Kaluuya) has a smooth start with Rose’s (Allison Williams) family. Her mother even offers to do a hypnotherapy session to help with his smoking addiction. The weekend seems to be going well for couple.
That is until the family locks Chris in the house and attempts to perform surgery to give his body to a blind man. It may go without saying thatthe relationship between Chris and Roseis done, with the protagonist narrowly escaping death.
8’While You Were Sleeping' (1995)
Does it count if the guy doesn’t know he’s dating someone? Lucy (Sandra Bullock) falls in love with a commuter while on the job as a fare collector for the Chicago Transit System.
When Lucy has the chance to save Peter’s (Peter Gallagher) life, she also gets the opportunity to claim she’s his girlfriend…since he’s in a coma. There is a mutual love between the main character and her faux beau’s family, but who will she end up going on a date with in the end?
9’Carrie' (1976)
Young Carrie (Sissy Spacek)has had a tough life. As if being bullied by peers and her mother isn’t enough, she gets her period at school and is ridiculed by the girls in the locker room. Her luck appears to change when she is asked to the prom by a popular and handsome hunk.
Although the date isn’t meant to be a prank, it could be classified as one of the worst on the list. Pig blood, electrocution, a fatal fire, and hundreds of deaths are part of the big night.
10’Rushmore' (1998)
Four people are on a date. “Oh, are they?” If three’s a crowd, then the dinner table is past capacity inRushmore’s epic date scene. Everyone seems uncomfortable as Max (Jason Schwartzman) attends a dinner with his adult crush and his friend, who also has eyes on the widowed teacher.
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To top it all off, Rosemary (Olivia Williams) brings her own date. Dr. Peter Flynn (Luke Wilson) is decked out in his O.R. scrubs as he tries to brush off the insults from a distraught Max. Luckily,Bill Murrayis there to keep his little buddy out of big trouble.
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