Share Your Awkward Date Stories
Do you have an awkward date story? We all do. Share your funniest, most awkward moments with us
We've all had them: bad dates, which--in the cold light of hindsight--are hilariously bad. Sometimes it's something you did, sometimes it's on them. There is, I believe, a lot of value in being able to laugh at yourself and your mistakes. To that end, here are a few stories from your local Patch editors.
Read on, if you dare...
"Fore!" – Grahame Turner, Brookline Patch Local Editor
Back in High School, I went on a double-date with some friends to Kimball's Farm. The plan was ice cream and a bucket of balls on the driving range, and we were most of the way through the latter. As it turns out, I am terrible at golf, and was struggling to get the ball past the 50- to 75-yard line.
I figured that what I needed was more power behind the swing to slice the ball further, and applied this hypothesis to the next few strokes. My date attempted to pass behind me, between the other couple, at just the wrong moment. Just as I was admiring my own follow-through, I felt a clunk through the golf club--I had hit my poor date in the back of the head with the club.
She was fine, and accepted my profuse apologies gracefully. It was fortunately not a very serious date, but we did remain "just friends" after the incident.
"Wild Horses Couldn't Stop Me" – Brooklyn Lowery, Wayland Patch Local Editor
Around Christmas 2006, my roommate, Emory, begged me to go line dancing with her when her mom came to town for the weekend. We needed to show her mom a true Nashville experience, so an evening at the The Wildhorse Saloon was in order. The Electric Slide was a stretch for me, but she was my roommate, so I agreed.
At the Wildhorse, we met a group of "regulars" with whom we shared mutual friends. I whispered to my roommate that one of those regulars was really cute. Jonathan, who happened to be a wonderful line dancer, and I were introduced.
I spent the rest of the night flailing like an octopus who sprouted extra legs as Jonathan patiently attempted to teach me to dance. I stomped on his toes, missed the beats, butchered the steps and otherwise embarrassed myself. Awkward as it was for me, he still asked for my number at the end of the night – we line danced at our wedding two years later.
"Baffled on the Swings" – Charlie Breitrose, Watertown Patch Local Editor
In graduate school I went out with a fellow journalism student, but I was never quite clear if it was actually a date. She called to see if I was free, and as luck had it (more like "as usual") I was. I picked her up and we drove around.
She said we should go to this park in town. I remember sitting on a swing when she told me her ex-boyfriend used to take her there. Then we went to a drive-in diner, where she also had frequented with her ex. We also swung by her place, but I was so baffled by that point that I didn't want to make a move. I still wonder if it was a date, or whether it was all about her ex-boyfriend. I suspect the latter, but she did want to hang out after that, too!(?)
"Everyone wants to date a musician" – Melanie Graham, Newton Patch Local Editor
In my early years as a music student I used to DJ at my college radio station. I got my fair share of awkward on-air phone calls, but most of them were easy to hang up on.
There was one guy who I would bump into at my workplace who listened to my show regularly and would always compliment me on it. I just brushed it off and figured I had finally encountered someone who shared my impeccable music taste (kidding).
Well, one day I was in town grabbing some lunch and he drove by and spotted me. He wanted to grab lunch too and I thought it was harmless and agreed. Then he insisted on paying for the lunch. And sharing dessert. And going to a movie.
Not only was I not even remotely interested, I had a boyfriend. It was one of those "oh God, what do I do now?" moments...why did he suddenly think we were on a date? Was I supposed to know this was a date? This is awkward.
I eventually got out of it, but it was followed with months of awkward run-ins, gifts (like records and mix tapes) and yes, more phone calls to the radio show. Eventually I ignored him enough for the "I have a boyfriend and I'm not interested" line to finally make sense in his brain...I think.
"Good Cop, Bad Cop" – Ryan Grannan-Doll, Waltham Patch Local Editor
In 2007, while working at Starbucks, I took a fellow employee out on a date. She was chatty during work hours, but that all changed once we arrived at the restaurant.
I'm a pretty talkative person with anybody, but I could not manage to generate a stimulating conversation with my date. I kept asking her questions about herself and expected her to do the same of me, but my efforts failed. She would give one-word answers, leaving me frustrated. It felt like an interrogation.
Editor's Note: This story appears in Acton, Brookline, Newton, Jamaica Plain, Sudbury, Waltham, Watertown, Wayland, Weston, and Woburn.
Unless you ask permission from the other people in your story, we ask that you keep the other person anonymous--if names must be used, make up new names for other people in the story.
Brent Blogs
7:12 pm on Sunday, May 5, 2013
Hey there! I was just wondering if it's too late for me to share some of my own awkward dating stories. I actually did a vlog that contains four awkward date stories of my own:
https://www.youtube.com/watch?v=5P683Ka414M