With 21 years worth of dating history under my belt, I had to think long and hard about which of my many bad dates would hit #1 on my personal Casey Kasem’s Top 40 Emotionally Scarring Dates of All Time. Would it be the guy the guy who showed off his NRA card during dinner? The guy who had one of those nose rings that connected with a chain to an earring? Or maybe the guy who made a bunch of anti-Semitic comments while he was walking me home? So much to choose from [sigh].
But there was one gentleman who kept bobbing back to the surface at every painful review. Swashbuckling Steve, this one’s for you.
As an adult, if you go on a really bad date, you can always black it out or pretend that it never happened. At the very least, you can wait until you’re super drunk before you disclose the shameful details to your friends, family, and random passers-by on the street. And by that time, the whole experience has likely turned the corner from tragic to tragically funny anyway.
But in high school, that’s where the real damage is done. Forced to trot out potential paramours in front of your parents and siblings for them to judge and snicker about while you’re innocently off at the Wendy’s sharing a Frosty and some $.99 fries. It’s the worst.
Picture it: 1995. I had just gotten my braces off and was about to graduate high school. At a multi-school fundraiser (where I sang “Eat for Two” by Natalie Merchant [NOTE: I do not know why I felt that was an appropriate song choice for a HS fundraiser.]), I met an adorable and seemingly charming boy from the next town over . He presented me with fistful of cow tails and asked for my telephone number. Also, he had a ponytail. Obviously, I was quite smitten.
Over the next few weeks we talked on the phone constantly (although I probably should have been alerted by the fact that he exclusively wanted to brag about his role in a community theater production of “The Importance of Being Ernest” and repeatedly put me on hold to talk to someone else on call waiting), but our lack of cars made it impossible for us to see each other. But then, magically, he was able to secure a ride to my high school graduation. He would dress up! He would sit with my parents! He would come out to Friendly’s with us after the ceremony! It was all too perfect for words. UNTIL… [insert ominous music]
HE SHOWED UP TO MY HIGH SCHOOL GRADUATION IN A PIRATE COSTUME.
The worst part was that he didn’t even realize it. He called it his “fancy outfit” and was apparently completely oblivious to the fact that the combination of puffy shirt, vest, single gold hoop earring, tall boots tucked into pants, and tasseled purple silk waist sash ALWAYS EQUALS PIRATE . And then he proceeded to mingle politely with my family as if nothing was weird.
I was humiliated. Needless to say, he did not get the Friendly’s invite. But, my parents do still like to mention it at holidays.
So, there it is. Not as gross as the guy who farted a lot in bed, not as annoying as the guy who only spoke in puns… but Swashbuckling Steve established a level of adolescent embarrassment that will last me a lifetime*.
Think you can do worse? We’d love to hear your chart topping bad date stories (and frankly, it would make me feel better about my poor life decisions)!
*FINAL NOTE: It would later come to light after a series of unbelievable coincidences that Swashbuckling Steve was putting me on hold repeatedly because he was dating another girl at the same time. That girl would become a good friend of mine, and reveal over too much wine one night that SS had taken her to the PROM in his pirate outfit. Also, that he couldn’t find both boots, so he wore one boot and one shoe (I think she might win this one).