We’ve all had them in real life – dates that have gone horribly wrong. And some similar scenarios may have been depicted in some of the movies we have probably seen. Some of the worst have actually come from movies of the past that many current moviegoers may not ever have seen.

So, let’s go back in time a bit and look at five movie plots that have depicted horrible dates – funny, serious or just downright hideous.

There’s Something About Mary

Most movie junkies have seen this one. It is funny, poignant, and leaves viewers with a mix of feelings. It’s just a “feel-good” film. But there is a hilarious episode of a date gone wrong.
Ted has a date with Mary for prom. He arrives in a limo for the big night but must use the bathroom. He proceeds to catch all of his male junk in the teeth of his zipper, and Mary’s stepdad is unable to help. Ted’s big date ends with an ambulance trip to the hospital.

The Graduate

Who has not viewed this flick a dozen times? It’s just a classic. Remember the date between Ben and Elaine? Ben had been pressured into this date by their business-partner fathers but promised his lover, Elaine’s mother, that he would make it horrible.
And he did. He ignored her at times, insulted her at others, and then capped off the evening by taking her to a strip club.

American Pie

Sometimes a date includes the first time for sex. And this is exactly what weaves the plot of this coming-of-age movie. Five boys have made a pact to have sex before they graduate from high school. Jim decides that this event will occur with foreign exchange student Nadia. And he’s successful to a point.
But Jim has forgotten about the webcam he and his friends installed in his bedroom. And the entire thing is live-streamed for all to see, including fellow students, his parents, and even her sponsors who yank her and send her back home.


Cher is the typical California privileged high school girl – beautiful, rich, and popular. She is the recipient of lots of compliments on her clothing style by Christian, a new guy at her high school. She is determined for them to become an item.

Her first step? Put on her sexiest dress and invite him over to watch movies. She is convinced the date will turn into more than that.

But it did not. She discovered, as her friends kept telling her, that Christian was gay. Perhaps if an awesome dating app had been around in those days, Cher and Christian might have chatted online, and Cher wouldn’t be so “clueless.”

The Invention of Lying

There are people who are honest to a fault, never even telling a little white lie that might avoid hurting someone’s feelings. This is the case with Anna who has accepted a date with Mark, a writer.

Mark waits a long time for Anna to come to the door that night. When she finally does, she tells him it took her so long because she was masturbating. It gets worse. She also tells him that there will be no more dates because he is unattractive and doesn’t have enough money. Welp.

Just a Taste…

So, you may not have had a date as bad as any of these. Or you may have had much worse. It happens. These five are just a smattering of a long and never-ending parade of bad dates in cinema. And they do depict some realistic possibilities in our own lives. And in many cases, they can provide some comic relief in an otherwise serious or boring film.