13 Worst First Dates In Movies of All Time

Cameron Diaz in Something About Mary

Romances, comedies, dramas and even horror films all house some of the most romantic moments in Hollywood history. But what of those that don’t? The first date is one of much anxiety, something that isn’t lost on the film industry. The first date story has been told and retold, manipulated in whatever way necessary to drive the plot of a film.

First dates are almost always uncomfortable, nerve-wracking and undoubtedly awkward. Still, these cinematic first dates take the cake. Even your worst dating story doesn’t measure up to the truly mortifying, awful and even terrifying first dates that made this list.

Here are the 13 Worst First Dates In Movies of All Time.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Ben Stiller in Along Came Polly
Start Now

13 Along Came Polly (2004)

Ben Stiller in Along Came Polly

This 2004 romantic comedy starring Ben Stiller and Jennifer Aniston is home to one of the funniest, worst first dates in film. Reuben Feffer (Stiller) is a type-A, overly organized and cautious man whose life falls into disarray when an old classmate, his complete opposite, reenters his life and turns things upside down.

On their first date, Reuben and Polly (Aniston) go to a Moroccan restaurant for dinner, something that Reuben knows won’t sit well, but forces himself to do anyway to impress his date. Unfortunately, things don’t end well for him. Instead of spending the night getting to know Polly, like he planned, he spends the night in the bathroom, with plenty of trouble to go around.

12 American Pie (1999)

Jason Biggs and Shannon Elizabeth in American Pie

This film consists of more awkwardness in one scene than most films contain in their entirety, but that’s what makes the comedy so great. The story follows four teenage boys who make a pact to lose their virginity before prom night, a task that they find far more difficult than initially expected.

The worst first date includes a hot, foreign exchange student, a nerdy guy and the most dated webcam scene you’ve ever seen. Jim Levenstein (Jason Biggs) turns on his camera in hopes of catching his study date, Nadia (Shannon Elizabeth), while she’s changing, but things go terribly wrong when he reenters the room and forgets to turn it off, allowing the world to see him fumble his way through a failed sexual encounter. Let’s just say, things don’t end the way he would’ve liked them too, and the worst part – the entire school watched.

11 Blind Date (1987)

Bruce Willis and Kim Basinger in Blind Date

A film entirely circled around a blind date is sure to be one of the worst, even if it does star Bruce Willis. Walter Davis (Willis) is a hard working guy, who puts the emphasis on his job above all else, including his appearance and his love life. It isn’t until he needs a date for a business dinner that he reaches out to ask his brother to set him up on a blind date. Unfortunately for him, the date he’s using to impress his boss is actually going to cause his career’s demise.

Walter’s brother warns him before the date with Nadia (Kim Basinger) that if she drinks, she loses control, something that expectedly happens, especially when her ex-boyfriend enters the picture. This is the worst case scenario when it comes to a blind date, and the comedy tells the story all too well.

10 Clueless (1995)

Alicia Silverstone in Clueless

This film, an innovative reworking of Jane Austen’s Emma, follows high school it-girl Cher (Alicia Silverstone) as she attempts to increase a new student’s popularity and play matchmaker in the meantime. However, as her matchmaking schemes begin to backfire, causing some discord in her own life, Cher is forced to reconsider her meddling and its repercussions.

The worst first date in the film takes place a bit later, when a new student named Christian enters the picture. Cher immediately falls for the new guy, and attempts to claim him as her boyfriend. However, this doesn’t work out well for her in the end as Christian doesn’t seem interested in her, and eventually it needs to be spelled out for her that the new guy is actually gay. Not exactly the outcome she wanted.

9 The Graduate (1967)

In this 1967 comedy/drama/romance film, a recent college graduate (Dustin Hoffman) finds himself in the middle of an affair with an older woman (Anne Bancroft). But things become much more complex when Ben (Hoffman) falls for Mrs. Robinson’s (Bancroft) daughter, Elaine (Katharine Ross).

The intricate family situation leaves Ben confused and in trouble with all of the Robinson women, though by the end of the film his only goal is to marry Elaine. The awkwardness of his first date with Mrs. Robinson, the affair that didn’t last, and the awkwardness the audience feels on his date with Elaine, knowing that he's been with her mother, lands this film on the list of worst first dates in cinema history.

8 It Follows (2014)

it follows maika monroe horror films nightmares

An oddball horror movie with a student film feel, It Follows is a creepy telling of the horrors of a first date, and reveals just how little you can know a person. Annie (Bailey Spry) is an attractive young girl that always seems to be dating someone new. But while her sister and friends believe this is just another boy, they’re in for a surprise when Annie is dropped off, half-naked, in the front of their house, completely changed.

Annie’s date concludes with a sexual encounter gone wrong when Hugh (Jake Weary) uses chloroform to knock her out and tie her to a wheelchair, telling her she will now be haunted by a supernatural entity that doesn’t quit. She doesn’t know what to believe until strange beings that only she can see continually follow her. Definitely not the best first date.

7 My Best Friend’s Girl (2008)

Kate Hudson in My Best Friend's Girl

This comedy starring Kate Hudson and Dane Cook is raunchy, quirky and absolutely hilarious, but is also home to several of the worst first dates ever. Tank (Cook) is the ultimate wingman – he gets paid to take men’s ex-girlfriends on the worst dates they’ve ever been on in hopes of driving the women back into their ex’s arms.

Of course, this is brings us to the worst first dates ever, and there are tons of them. But the worst one definitely involves Tank’s best friend’s (Jason Biggs) love interest, Alexis (Hudson). When Tank agrees to take her on a date, he accidentally falls for her, though he still attempts to make it the worst date of her life.

6 Observe & Report (2009)

Seth Rogen and Anna Faris in Observe & Report

This plot follows Ronnie (Seth Rogan) as a bi-polar, mall security guard that’s called into action when a flasher attempts to use the public location for his own agenda. And with stars like Seth Rogen, Anna Faris, Michael Peña and Ray Liotta, you can bet it’s going to be a comedy, but no one was quite ready for the dark comedy that it was.

Following their first date, Ronnie and Brandi (Farris) engage in what can only be described as a “date rape” scene, in which Ronnie is on top of Brandi, who appears to be passed out on the bed with vomit on the pillow, obviously non-responsive to her surroundings. However, the scene is made “funny” when she lets out a one-liner that makes it appear as if she’s been conscious the entire time. It’s a controversial scene for sure, but also earns a spot as one of the worst first dates.

5 Rushmore (1998)

Jason Schwartzmann in Rushmore

Starring Jason Schwartzman, Bill Murray and Olivia Williams, Rushmore is the story of a Max, 15-year-old attending a private school who is not doing so well in his classes, and finds out he is put on academic probation. Of course, this is also where he stumbles into love with Miss Cross, a teacher. This gets complicated when another man, a father of some of the boys that attend the school, falls in love with her as well.

This love triangle is home to another extremely awkward, though hilarious, first date scene, where Max (Schwartzman) has invited Miss Cross (Olivia Williams) to dinner following his school play, though she’s invited some guests of her own, making for a joke-filled, awkward date that’s certainly not what he had in mind.

4 Shame (2011)

Michael Fassbender in Shame

Brandon (Michael Fassbender) has a private life that he’d like to keep that way, but when his sister comes into town indefinitely, things don’t go quite as planned. Brandon’s sexual addiction prohibits him from getting, and maintaining, meaningful relationships, something visibly seen in the scene with him and his date, Marianne (Nicole Beharie).

This date includes extremely awkward conversation, silences and end of the night hesitation, definitely not leaving the greatest of first impressions, but also not one of the worst dates on this list. Still, the audience’s knowledge of Brandon’s attachment issues make for an even more awkward scene.

3 Something About Mary (1998)

Cameron Diaz in Something About Mary

High school was a rough time for Ted (Ben Stiller), even after his dream girl, Mary (Cameron Diaz), asked him to the senior prom. Now, years later, Ted is given another opportunity to take her on a date, and do it right. This romantic comedy is hilarious, awkward and plays big time on the insecurities of men when it comes to women they believe are “out of their league.”

Another awkward date for Stiller, Something About Mary is home to one of the most mortifying date scenes ever. Or, maybe two. Back in high school, Ted had his dream date for the prom until an embarrassing accident that left him hospitalized. Now that he has another chance, there’s another embarrassing mishap that he’s hoping doesn’t cost him his second chance with his dream girl.

2 Taxi Driver (1976)

Robert De Niro in Taxi Driver

This Martin Scorsese film starring Robert De Niro and Jodie Foster follows a mentally unstable Vietnam war veteran that works as a nighttime cabbie in New York City. He’s driven to violence by the NYC, sleazy nightlife and also attempts to save a young prostitute in the process.

The first date in this film involves an adult film and a very unhappy date. Travis (De Niro) takes his date to the porno, convincing her that a lot of couples do it and that it’ll be fun. She hesitantly goes along with it, but just a few minutes into the movie and she’s had enough, and leaves in a cab.

1 When Harry Met Sally (1989)

Meg Ryan in When Harry Met Sally

One of the most well-known romantic comedies out there, When Harry Met Sally, starring Billy Crystal and Meg Ryan, is the most traditional telling of a friendship between a male and a female and the repercussions that are in store if that friendship becomes anything more, even for a second.

For this awkward date, Harry (Crystal) and Sally (Ryan) attempt a double date, which results in extremely awkward and strained conversation, and at the end of the night, the opposite dates end up with one finding an excuse to leave with one another, which in turn leaves Harry and Sally alone, again. Just more proof that double dates don’t actually work.


Did we miss a first date that you think was worse? Let us know in the comments!

More in Lists