5.8k voters

The Most Epic Sexting Fails of All Time

Updated March 19, 2020 17.9k votes 5.8k voters 5.9m views34 items

Technology is fickle, and when mixed with alcohol, communication with the opposite gender is ripe with opportunity to go wrong. Everyone has been there; you've had a little too much to drink and are now looking to fill that empty void in your life with some good old-fashioned, no-strings-attached copulation. But alas, your vision is blurry, your memory is foggy, and you're kicking yourself for not writing down the number of that catch at the bar clearly enough.

This is when you shoot a desperate message into cyberspace, hoping it'll land where you want. Most of the time, if you have the wrong number, the stranger will forgive your trespass and spare you the embarrassment via texts, allowing you to move along by not responding. Sometimes, however, fate leads you to a jokester who wants you to know just how funny they are, and a screen capture of your sexy message fail is born.

Sometimes these situations cannot be chalked up to a mere miss of digits. Sometimes you reach exactly the person you intended to contact, only to find that your naughty text advances are not welcome at all. Perhaps it was an ex or just someone whose friendliness you misinterpreted as flirtation. Maybe autocorrect swooped in to steal a steamy moment between you and your beloved for a real text message fail. Either way, check out this list of hilarious sexting fails, and don't forget to upvote the funniest blunders!

  • 1

    I Think He Blew It...

    Photo: Metaweb / CC-BY
  • 2

    It's Dark, And She's Honest

    Photo: flickr / CC0
  • 3

    This Guy Is Cheeky, But Not In The Right Way

  • 4

    Your Bad Indeed, But Look What You Gained!

    Photo: Pinterest