Teachers Share Most Cringe-Worthy Dating Expriences

Jaden Keith, Staff Writer

With Valentine’s Day quickly approaching, shops and social media are flooded with flowers, chocolates, and dates. Some dates are better than others, while some transcend the term ‘bad date’ and become an infamously cringe inducing story for years to come. Even the teachers here at school have stories about some of their most awkward and most cringe-worthy first dates.


The Phantom of the Club Night

Mrs. Bird, Biology Teacher

“When I was in college, some kid asked me out to ‘Club Night.’ Club Night was something my university puts on to showcase all the different clubs at the start of the semester, and I decided to check it out with him. So we get there, and we aren’t together for long when suddenly, he vanishes. The night goes on and I later find him with another girl. I approach him and say, ‘Hey, I’ve been looking for you’ and after that he stayed with me the rest of the night. He wasn’t very courteous to me and there was never a second date.”

Country vs. Classical

Mr. Massey, Chemistry Teacher

“One time, I took a girl out to a classical music concert. I was ready to enjoy the music with her but I soon found out she was more of a country music fan; she totally did not like classical music and she let me know it. It was all rather awkward and we never went on a second date.”


Mr. King, Chemistry and Engineering Teacher

“I had been on a few dates with this girl before, and this night I decided to take her to dinner and the movies. When I pick her up, she gets in the car and tells me that her friend was coming along as well. I was a bit hesitant but told her I didn’t mind if her friend came along. She introduces me to her friend and it’s a guy; we go to dinner, and I ended up not only paying for her and myself but him as well. I thought that was weird but I kind of just went with it. We get to the movie theater and she has to take a call, as she answers the phone I catch her saying, ‘Oh, I’m just hanging out with my boyfriend and my ex’. That’s when I pulled her aside and asked her to hang up. I asked her why she brought her ex-boyfriend on our date. She ended up going home with him that night. Needless to say, we never went on another date.”

Perm-anently Scarred

Mrs. Zachry, Spanish, English and Journalism teacher

“I was 17 and was working at Putt Putt and one of the shift-managers there asked me if I wanted to get something to eat. It didn’t sound quite like a date, so I decided to go. He came to my house to pick me up wearing slacks and nice clothes with his hair permed, but only in the back. I was so embarrassed that I had to go have dinner with him. I forget where we ate but I do remember the whole time we were eating he was trying to convince me to marry him so he could use me as his tax write off. He asked me on another date and I said, ‘no’. It was the most cringe-worthy date I ever went on.”

Stuck in Love

Coach Mackey, History Teacher and Coach

“I was in seventh grade and had a crush on this girl, and I took her on what was my first date ever. The date was fine, just a normal date, but when things came to an end, I decided to kiss her, and it was my first kiss. I had a retainer and she had braces and we got stuck. To top it all off, her dad was the one who had to help us get unstuck.”