Finding yourself back in the dating scene can shatter your confidence, no matter your age — especially when you find yourself on an awkward first date.
In these two authors’ experience, one of the best parts about, ahem, getting a little older is feeling comfortable in your skin (even if it’s not as taut as it once was). Having a larger collection of trips around the sun allows us to move through life with fewer awkward moments and with more grace and confidence.
That is, until we find ourselves back in the dating scene.
You’d think experience would count for more here. Surely, by now, we can make conversation with one person over a drink or dinner. We can ask questions, show interest and recognize when someone would rather talk about themselves for the entire evening. We’ve also learned that finding someone hot doesn’t obligate us to find them fascinating.
Still, there’s something sort of awful about sitting across from a person who is actively deciding whether they’d like to see you again. Suddenly, you’re hearing yourself talk. Have you mentioned your ex too much? Your children? Your dog? When did this become a detailed explanation of your job?
Was this just us? We didn’t think so.
So we asked friends how some of their first dates had gone, hoping to glean some advice for all of us should you find yourself heading back into the dating scene again. If experience hadn’t spared them the awkwardness, perhaps it had at least left them with a good story. They delivered.
To preserve egos, we’re using first names only. Read them and learn from these hard-earned first date fails — or just enjoy the laughs.
True Stories of First Date Fails (Mostly)
Your Place or Your Place?
Jake uses dating apps on and off. During an “on” week, he met a woman for a Friday-night drink. His house was on her route home from work, so a couple of days later, he invited her to dinner. She arrived and asked to take a shower. He’d anticipated cocktail service, but the towel service caught him off guard. After dinner and a drink, she asked to spend the night while he made a second round. They’d known each other only a few days, so he offered the couch if she was uncomfortable driving. She downed the second drink and left. Apparently, the couch wasn’t the room she’d been reading.
Lesson: Read the room … before assuming it’s the bedroom.
Heads or Heart?
Robert took a woman gallery-hopping downtown on First Friday. Somewhere between the art and the sushi, they stopped in a parking lot to collect a bag of heads — hairstyling practice heads, to be clear. A friend was selling them, and Robert wanted them for art props. It had started raining when the friend arrived, and the heads were shoved into a trash bag so thin that the faces looked like they were trying to escape. We wish we had her version of this story. Robert never saw her again. He does still have the heads.
Lesson: We all have baggage — but it shouldn’t be making eye contact.
Obviously Bowie
Allison was introduced to a musician because of their shared religious beliefs. He played accordion, and she thought that was cool, but things went downhill from there. She asked what music he was into, and he announced he’d anticipated the question. A musician being asked about music — who could have seen that coming? “Well, obviously, I’m into Bowie.” Obviously? He hadn’t donned a Labyrinth costume, no crystal balls, no Ziggy Stardust makeup, nothing obvious about it. The evening ended with her leaving the date in the dark on her bike. No second date, but “obviously Bowie” still gives her a good laugh.
Lesson: In this case, not even Jesus saves.
Somebody’s Settling
Ari dated a 38-year-old whose red flags could fill a Six Flags! She asked him about his plans for the next few years, and he said he “wanted to get settled into his house.” (He’d already lived there five years.) His kitchen trash can was a cardboard box beside the sink that he emptied weekly into the outdoor bin with no bag. The trash guys probably hated him, and the raccoons probably loved him.
Lesson: Let him settle in. You don’t have to settle.
Are You Feeling the Magic — or the Deviled Eggs?
When we asked Kate for stories on her entry back into the dating world, we couldn’t settle on just one story.
Once, she met a date downtown for apps and drinks. She wore a backless shirt (she said she’d done some pushups, and it was a good way to show off the results). He must have liked what he saw because when she got chilly and put on her jacket, he took that as an invitation to reach into the jacket to touch her back. The misreading of cues didn’t end there. “There were deviled eggs on the menu. I like deviled eggs. I did not want to eat deviled eggs in a bar on a first date. That’s, I think, verbatim what I relayed to him. He took that as a cue to order a plate of deviled eggs for the table.”
On another date downtown, things were going well. Then the magic happened. No, not chemistry. Another bar patron approached Kate and her date and offered some close-up magic. He then delivered about 10 minutes of tricks “absolutely rife with sexual innuendos, almost exclusively directed at me.” Kate found the magician funny, but by the time she left, she was tired. Her date walked her to the car, apparently hoping for a kiss. That would have required a different kind of magic.
Lesson: If at first you don’t succeed, try, try again. Not every first date ends well, but don’t let that stop you from going out again. (Also, shoot your shot if you’re an up-close magician, apparently.)
Solo Surprise
Or take Jamie’s approach. After an evening of Skee-Ball and lemonade with a man who definitely wasn’t the one, she realized she could take herself out and have just as much fun. Someone telling you you’re pretty is a nice bonus. But so is knowing you don’t need them to make it a good night.
Lesson: You can be good company for yourself.
And it wouldn’t be fair if we didn’t share a story of our own, right?
Bombs or Fireworks?
Carrie: I was 40 and freshly divorced when I ended up at a movie with Sergei. He’d been trying to get my number, and I’d refused, but a friend finally started a group text — on purpose I’m sure. He was 23 and in the Army. I wasn’t shopping in either department.
He and a female friend picked me up from Bristol Brewing to see Fury — a loud, bomby World War II Brad Pitt movie. Between the beer and the bombs, I spent much of it cringing into him — a convenient opportunity for him to put an arm around me. His friend didn’t know she was attending our first date. Neither did I. Thirteen years later, we’re still dating.
Lesson: Awkward doesn’t always mean it’s going to go badly.
Hat Trick
Laura: I was invited to a retirement party for a coworker from my former employer. There I ran into Todd, someone I had worked with 25 years ago. We were both married last time we saw each other. Not now, so I shared my number. He texted the next morning, and we made plans for the following weekend.
That Saturday, I was invited to a birthday party for two friends and had tickets to a CC hockey game. I had also wanted to see the wind-powered kinetic sculpture installation, The Windmill Project, below Pulpit Rock at UCCS. He was game for it all. This marathon date started around 3:30 p.m. and went late into the night.
I figured someone who could endure my friends, a full hockey game, and a nighttime hike on a first date was probably a keeper. Fast forward five years, and we went to the first CC hockey game this year — our first as a married couple.
Lesson: You never know when a first date might be your last first date.
Want to ease the pressure?
Keep in mind you’re not auditioning someone for the rest of your life. You’re deciding whether you want to spend another two hours — on another day — with them. Have some fun. Try our first date suggestions here. See how they handle a little nonsense. Just remember: “owns a trash can” is a reasonable standard.
