Funny Dating Disaster Stories

Funny Dating Disaster Stories

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The world of dating can be fraught with awkward encounters. First dates can be particularly hit-or-miss. Sometimes, the conversation flows and sparks fly. At other times, you might find yourself wanting to climb through a bathroom window just to get out of a bad date!


Though it can be hard to laugh about a painful encounter while you’re suffering through it, many bad dates can be funny in retrospect. Here are a few dating disaster stories that are guaranteed to make you cringe and laugh!


Let Me Entertain You


Most dates involve some discussion of one’s family and friends. This awful date, however, involved nothing but family-centered entertainment. Instead of taking his date out for lunch as they had planned, Rob invited Jessica to join him at his work desk for lunch. While splitting the lunch he had packed and brought to work, Rob decided to pull up a few videos on his computer. The first was a video of his father, an amateur musician, singing love songs at a local pub. Afterwards, in perhaps an awkward attempt to show off for his date, Rob queued up an episode of a home renovation show featuring his parents’ family home. Though Rob was interested in a second date, Jessica politely declined. A work-break lunch and family videos weren’t exactly her idea of romance! 

A Murderous Mishap


Robert noticed Carla while the pair were perusing a sporting goods store. As Carla was also looking at golf clubs, Robert began discussing the sport. The two hit it off and decided to go on a golfing date at a local country club.


Everything seemed to be going well until the fifth hole. Getting ready to swing, Robert noticed a group of cranes further down the fairway. Expecting his shot to soar above them, Robert swung, only to be surprised by his unexpectedly low drive. Robert’s jaw dropped, as did Carla’s, as his golf ball slammed into one of the birds, taking it down for good.

Robert profusely apologized for the accident, but for Carla, it was too much to handle. An animal lover at heart, she couldn’t bear to look at the dead bird. The crane’s life partner remained by its side, crying and morning its loss. The two finished their nine-hole game in silence. The tragic accident didn’t just kill a bird; the prospects of a future date were killed that afternoon as well.


Dating While Distracted


In this day and age, it’s not uncommon to feel as though potential partners are more enamored with their smartphones than they are with us. For this reason, Birgit was annoyed but unsurprised when her date repeatedly left their table to answer phone calls and respond to text messages during their restaurant meal. After stepping out numerous times, however, she was beginning to get genuinely upset. Towards the end of their dinner, Birgit’s waiter stopped by to provide her with a shocking revelation. Birgit’s date wasn’t actually having a love affair with his phone; in reality, he was enjoying a meal with another blonde beauty in a different section of the very same restaurant! Needless to say, this first date didn’t lead to a second one!


If The Shoe Fits


While waiting for their dinner reservation at a local bistro downtown, Anne convinced Hugo to spend a few minutes perusing a local shoe store. Anne seemed to be enjoying herself, trying on pair after pair of boots and stilettos. It wasn’t long, however, before the pair missed their reservation. Anne, however, continued with her shoe shopping, despite Hugo’s growing impatience. An hour after their scheduled reservation time, Hugo finally ushered Anne out the door. On their way to the restaurant, however, Anne began giggling. She opened her purse to reveal four pairs of shoes that she had shoplifted from the store! Despite her insistence that it “wasn’t a big deal,” Anne’s kleptomania was a turn-off for Hugo. For him, Anne’s illegal pleasure-seeking was an obvious deal-breaker!


Unrehearsed and Uncomfortable


Sophie was enjoying her date with Walter; he seemed charming, funny, and intelligent. The two had watched a film and enjoyed a nice meal before heading back to Walter’s apartment for a drink. Though Sophie knew her date participated in improvisational comedy, she didn’t expect to take part in a comedy performance of her own. Walter, however, insisted that they play an improv game for the next hour. All seemed fine until Walter demanded that Sophie perform as his mother. Uncomfortable with the strangely incestuous roleplay, Sophie called it a night and grabbed a taxi home. Perhaps Walter found another woman who could handle his comical “mama drama!”


In Conclusion:


Whether you’re getting to know someone new online or in-person, there’s always the chance that the person you’re talking to will behave in an unexpected way. Tragicomedy can affect us personally, too, leaving potential partners running for the hills. Though you might have to suffer through a few bad dates before finding a steady beau, you might just gain a funny story to tell in the future!



Photo: © ianrward /

Editor, 01/03/2019