Top 10 Awkward Movie Dates

Edward D. Wood Jr. had his fair share of baggage, but few would deny that the director was a passionate, determined, and all-around cheerful guy. When he’s stranded on a broken-down carnival ride with his future wife, Kathy, Wood decides to divulge his greatest secret: his guilty pleasure of cross-dressing. While most women would be running for the hills, Kathy decides to accept this delightfully quirky fella for who he is. It goes to show that sometimes it’s best to get everything out in the open on the first date.

It’s hard to imagine anybody could possibly be more awkward than Brick Tamland. The weatherman meets his match in the sequel to “Anchorman,” however, upon encountering incompetent office worker Chani Lastnamé. Like a five-year-old on the playground, the shy Brick asks Chani to go to a date with him. As strange as it sounds, a Laundromat is the perfect romantic setting for these empty-headed lovebirds. After downing several sodas, the two engage in their first kiss and throw themselves a pants party. Talk about an upgrade from shoulder touching.

Parry is a delusional homeless man who lost his wife and sanity in a shooting. Lydia is a mousy recluse he’s been following without ever directly approaching. This scene from “The Fisher King” strikes the perfect balance between uncomfortable and romantic as Parry confesses his hard-on for Lydia. Dishing out his feelings, Parry could easily come off as a creepy stalker who needs psychological help. Lydia can see in Parry’s wide eyes, though, that he’s 100% sincere about his affection for her. It’s totally bizarre, but sometimes so is love.

Handsome, sharp, and wealthy, Patrick Bateman might seem like a catch. Little does anyone realize, however, that he’s also a chainsaw-wielding psychopath. While on a date with his secretary Jean, Bateman plays with lethal instruments in his apartment. As the two casually converse, the audience is convinced the unsuspecting Jean will become Bateman’s next victim. But before he can fire a nail gun at his employee’s head, she’s saved by an answering machine. Bateman decides to let Jean live, leaving her blissfully unaware of how close she came to certain death.

If you sleep with someone on the first date, be prepared to receive some life-altering news on your second date. In this scene from “Knocked Up,” Alison prepares to inform her flabby-chested one-night stand, Ben, that there’s a bun in her oven. Before dropping the bombshell, she hopes to learn a little more about the father of her baby. She only grows more concerned as Ben prattles on. When Alison finally breaks the news, Ben naturally reacts like an immature child. That’s why you always wear a condom, kids.

What if people always told each other exactly what they were thinking on dates? Chances are they’d never speak again. The romantic leads aren’t always upfront with one another in “Annie Hall.” But the audience gets a glimpse at what’s on Alvy’s and Annie’s minds as they have drinks on a balcony. Through subtitles, the two express their internal insecurities, curiosities, and sexual urges. They mask all of these repressed thoughts by uneasily discussing photography. It’s a funny and clever commentary on how all conservations carry subtext – even small talk.

The Coen Brothers are masters of uncomfortable comedy, as represented in this scene from “Fargo.” The very pregnant Marge Gunderson thinks that she’s going out to a friendly dinner with her high school chum, Mike Yanagita. But the lonely Mike has other intentions. Margie is too kind to flat-out shoot Mike down. As he invades her comfort zone, though, she tries to gracefully slip out. Things only get more awkward as Mike breaks down in tears over his pathetic life, which he’s been lying about to Margie this whole time.

When Ted scores Mary as a prom date, it seems too good to be true. Yet, everything that can possibly go wrong for the braces-faced teenager does go horribly wrong as he’s beaten by Mary’s mentally challenged brother, mistaken for a peeper, and suffers an accident with his zipper. If you assume matters can’t get any more humiliating from there, think again. Ted gets a second shot with his dream girl thirteen years later, but that date takes an equally awkward turn after an incident with some *cough* “hair gel.”

Taking your own mother to the school dance is one thing. Having your mother come onto you at the school dance is quite another. Trapped in 1955, Marty McFly finds himself at the Enchantment Under the Sea dance with the teenage version of his mom. As part of a ruse to bring his parents together, the nervous Marty needs to make a move on her. But, before he can work up the courage, his frisky date lands one right on her future son’s lips. Immediately, she finds something isn’t right. Thank god they didn’t go any further.

Before we kiss our top pick goodnight, here are a few honorable mentions:
- Hi, Mr. Gladstone
“The Graduate” (1967)
- Penis-Nosed Woman
“Deuce Bigalow: European Gigolo” (2005)
- I Think It’s the Right Thing to Do
Legally Blonde (2001)
- Chin Balls
“Movie 43” (2013)
- Too Much For a First Date?
“Baby Mama” (2008)

All Travis Bickle wants is to make a connection with another human being and to serve a purpose. However, he just doesn’t know how to function in this world. The audience begins to see just how socially inept Travis is when he takes his love interest Betsy to a movie. Not your typical date movie, but a Swedish sex education film. As you might expect, Betsy is not impressed. The further she pushes Travis away, the further he descends into madness as this unstable taxi driver attempts to find his place.

Do you agree with our list? What movie dates made you cringe? For more entertaining Top 10s published every day, be sure to subscribe to WatchMojo.com.