Diary of Dating Disasters

Could a first date get any worse?


Chase Berger, News Section Editor

Amid the happy couples celebrating their love, there are some who reflect on their potential and past prospects and shudder. They decide they would happily spend Valentine’s Day alone than ever give their past dating disasters another attempt. Some dating stories are so catastrophic that they sound as if they are fictive tales pulled from the imagination. Unfortunately for everyone, the following stories are true.


The first red flag Jules discovered on their first date with a boy to Build-a-Bear was him expecting them to pay for his Build-a-Bear. While this would not normally be a problem, Jules was put off by finding that their date expected it. The second much more alarming red flag occurred when the boy ate the pretzels he dropped off the filthy mall floor. There was not a second date.

  • Jules Gonzales ‘24


Alejandra is a woman who does not regret much but would consider her ex-boyfriend to be one thing she does. While she was not looking for a relationship during quarantine, she reluctantly agreed to be exclusive with a man who wanted to be exclusive with her. Soon after they began to date, he revealed his true colors. He started to become controlling and even said multiple different slurs in passing conversations. After calling him out and trying to hold him accountable, she began to distance herself from him before finally cutting him off completely.

  • Alejandra Correa ‘24


For Emily, working long hours at her job had never proven to be a problem. Sure, she got home late and stayed up even later to finish her university homework, but the money was nice. Unfortunately, a problem arose when a boy decided he wanted to pursue her at the worst time possible and maybe also the creepiest time possible. After they finished closing together, he walked to her car, practically cornering her into a conversation for twenty minutes before he let her go home. Rest assured, Emily did not agree to go on a date with him.

  • Emily Olsen ‘23


What Alayna hoped would be a fun day turned out to be a horrible decision. While on a casual date with a boy, a bad omen appeared before her in the shape of a fortune cookie. The slip of paper inside claimed that the love of her life was right in front of her; it was wrong, so very wrong. During the date, several red flags appeared (he only spoke about himself, never caring to ask her anything, and mentioned his last relationship several times), and she immediately threw away the fortune after the date. However, every couple of months, he resurfaces and continues to make her life awkward.

  • Alayna Brown ‘25


First dates can make or break a future relationship, so most people do their best to prevent any awkward encounters or hiccups. First dates are supposed to only involve the potential couple, right? Well, apparently Nick’s date didn’t get the memo. After spending $75 on an Uber to the fair, imagine his surprise to find his date and her entire family: father, mother, little brother, and little sister. Talk about an awkward first date.

  • Nicholas Suarez ‘24