Just like dating, first impressions don’t always tell you everything you need to know. Our recent survey ended up producing some of the amusing, weird, and yes, even cringeworthy first date tales from people all over America. From embarrassing meetings to sad events, these stories showcase the hilarious route of love.
Of note were several retiree non-travelers who told their stories, illustrating their romantic evenings gone hilariously awry and making them some of the most memorable tales. If some dates led to contentment with how the story ended, other dates led to surprise encounters or learnings that proved to be the best surprise.
Traffic Troubles and Awkward Turns
John, a 72-year-old retiree from Atwater, California, was almost caught in the unfortunate twist of fate on his first date in Wichita. Unfamiliar with the city’s traffic laws, John tried a very dangerous U-turn on a one-way street.
I drove down the wrong direction on a one way ramp,” said John. It had been super uncomfortable to begin with, but that was the thing that really cut the camel’s back. Even with the wardrobe misstep, John was able to steer clear of any other date disasters for the remainder of the evening.
Rick, 68 Illinois, showed up with a bottle of wine on his first date. When he arrived, he found out that his date and her circle of friends were all recovering alcoholics.
When I got there, I found out that the gentleman and all his buddies were all recovering alcoholics. Within a few days we had tucked the bottle away. Rick stated. He observed that his date had drunk two cocktails to his one in only half an hour. The next day he wanted to call her and tell her it wasn’t gonna happen.
Uncomfortable Moments
Cristine, a 68-year-old artist from Arizona, went on the worst first date ever. Because her colleagues bullied her into it. “I agreed because he was my superior and because I was hungry,” she said. Cristine, who wasn’t looking to date anyone at the time, didn’t really want to do this, but felt she had to humor her co-worker.
Allison is a PhD researcher at 44, from Georgia. She had a bit of a mishap over her biking to the prom date. “After about 1km, my crutch slipped, I tumbled – my leg was in a full brace, so it couldn’t bend, and I landed hard on my other side,” she explained. Her date’s response was equally awkward as he remarked, “I thought your profile claimed you were athletic!”
Louisa, a 25-year-old from California, encountered an odd situation when her date asked if she was having a good time mid-meal. That’s when their conversation got really weird, as Louisa Xizhen Jiang ’25 started recounting a compliment from a third party on her date’s outfit. “This guy walks in – T-shirt and white boxers, the kind with the flap!” she recounted.
I explained that although I was enjoying myself, I was not truly feeling romantic chemistry,” Louisa expanded. She continued by noting that, once she shared her feelings, the conversation went from tense to uncomfortable silence before her date spoke.
The Unexpected Escapes
Geoff from Georgia shared a fateful blind date that ended up blossoming in an unexpected way after a shaky start. “We had a fantastic evening and hit it off extremely well,” he shared. And often, in spite of the initial jitters or missteps, those first dates can blossom into something beautiful and lasting.
Aliyaa, 68, of Michigan, vividly recalled an in-person coffee date she arranged via a matrimonial portal. This unforgettable meeting happened fifteen years ago. The story of how it played out is less clear. It was clear that it was not the way that encounter should have gone.
For Jennifer, a 53-year-old magazine editor from Maine, that posed a different kind of inviting obstacle. Like on her 2013 first date at a coffee shop in Frederick, Maryland. On top of that, the air conditioning was broken, creating an unpleasant working environment that neither side could overlook.
Cristine, too, came up with an on-the-date exit strategy that night, which included calling her best friend to get her out of there. I was disinclined to date,” she said again as she recounted her story.