Over the year and a half I was active with online dating before meeting Cosmo, I met some doozies, and one particular worst first date.
Early in my second dating go-round, after “Sam” died, I had a doomed, painful first-and-only date with a man I met on a dating site. I don’t at all blame the dating site. I should have known better.
I’m not likely to ever forget it, because no other date made me feel so small and so bad about myself.
The Worst First Date I Ever Had
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If I had trusted my gut, I could have avoided my worst first date.
Everything went crazy wrong from the second we met.
The date played out badly from beginning to end.
Other people tell their worst first date stories.
Have you ever witnessed someone else’s bad first date?
How I turned another bad date into an okay date.
If I had trusted my gut, I could have avoided my worst first date.
In hindsight, I saw the signs that he wasn’t for me in the few emails and phone calls we exchanged before meeting. But I think I was still getting my dating sea legs. I too easily gave people the benefit of the doubt, even when I shouldn’t.
I didn’t trust my gut and I hadn’t built up a strong front yet to take rejection, and ward off the awful way it can make you feel.
As always, I suggested meeting for coffee, because it puts less pressure on both people, and it’s easier to cut it short if things go wrong.
But he insisted we have dinner at a local restaurant he hadn’t been to in years. It was on a beautiful lake very near my home and the setting was very romantic.
He had said a few times in emails and calls that I looked so sexy in my profile photo. He wanted to have a romantic dinner with me.
Against my better judgement, I agreed, even though he was building this up way too much.
We met outside the restaurant on the boardwalk alongside the lake. It was a lovely Spring evening.
Everything went crazy wrong from the second we met.
As I approached him, I could see his expression change from curiosity to disappointment. Clearly and instantly he was unhappy with the way I looked, before I even said a word.
I’m no beauty queen, but I’ve been told many times that I’m attractive. I’m fit and I have a good figure that I know how to accentuate with form-fitting clothes. Besides, my profile photo represented me very well. He would have had no surprises about the way I looked.
I didn’t understand until after the date ended and I thought long and hard about it . . . he wanted to run.
He couldn’t wait to get out of there, but he had committed to dinner so he sat it out. Reluctantly and disinterestedly.
He had made a reservation and when we walked into the restaurant we were asked if we wanted to sit inside or outside at a table on the boardwalk.
I looked at him and asked what he preferred, then noticed he was kind of glaring at me like he was mad. Foolishly, I dismissed it. I figured I didn’t know him well enough to read him.
He shrugged heavily and said “I don’t care” like a petulant child. That didn’t feel right, but I plowed on.
In hindsight, I wish I had said right then, “Why don’t we cut this short. I don’t think things are working out.” But I didn’t.
The date played out badly from beginning to end.
We took a table inside the restaurant and the agony began. I tried to engage him in conversation, asking questions about his work, family, hobbies, etc., based on what had been on his profile.
He gave me mostly monosyllabic answers and didn’t reciprocate with questions for me. Not even a hint of a smile crossed his face. He rarely looked me in the eyes. He was actually kind of rude.
I asked him some question related to his work and he snapped, “I don’t want to talk about that”.
Looking back, I don’t know why I didn’t see that he was disinterested and biding time until he could flee.
I was so oblivious I ordered dessert, which I can recall now made him cringe. He probably felt he was too much of a gentleman to just end the date.
When the check came, I offered to split it, but he firmly said “No”.
He raced out before me, barely holding the door behind him. I had a hard time keeping up with him as he sprinted towards his car.
The restaurant was in a notoriously difficult area to find parking. He was parked right nearby, but he didn’t ask me where I parked.
I was quite a distance away and it was after dark. The walk to my car was not well lit and no one was around. I guess he didn’t care what happened to me.
He unconvincingly said he’d call me.
Afterwards, I spent some time feeling bad about myself, but I got over it. I could never have a healthy relationship with someone who could treat anyone that way.
I realized how wrong he was for me in so many ways . . . besides his nasty temperament and unkindness.
Lessons I learned from this bad date
- When someone treats me this way, don’t take it to heart. It’s a reflection on his character, not mine.
- It was just a date. So what if he wasn’t attracted to me. He wasn’t an ideal partner anyway.
- It has to work for both of us to work at all. If one of us isn’t into the other, it’s a losing proposition.
- If I’m on a bad date like this, it’s okay for me to politely end it whenever I want to.
- Chalk it up to needing more experience dating. In fact, once I did so, I ruled out people like him before going on any dates with them.
Other people tell their worst first date stories.
Anyone who has been dating for even only a few months probably has a worst first date story of their own.
For fun (and maybe enlightenment), let’s look at some of them.
These are some of the responses The Tonight Show’s Jimmy Fallon got when he asked viewers for feedback in a tweet with the hashtag #WorstFirstDate:
I went on a lovely date with someone I met online. Had a great time. After we finished dinner, she discovers over 15 missed calls from her family. Apparently, her mom did a Google search on me. Surprise! She found out that we were actually cousins.”
“My friends fixed me up on a blind date. Turned out to be my landlord and I was a month behind on rent.”
“The only thing my date could talk about was war and how proud he was that his country was one of the invaders. His country invaded mine.”
“He used a lint roller on my shirt and pants before he would let me in his car.”
“On a lunch date, the handsome guy told me he spoke 4 languages…one of them was “Math”…then proceeded to ask me about my German heritage explaining how he wanted to make sure he would have blonde-haired, blue-eyed Aryan children.”
I went on a first date with a guy who spent the whole time complaining about how his ex “screwed him over” then proceeded to cry and told me I reminded him of her.
“Guy pressured me for months into going on a date with him and when I finally said okay, be brought his mom.
Have you ever witnessed someone else’s bad first date?
Have you ever been out, say, having coffee or a meal and watched a couple who were clearly on a bad first date try to make the best of it . . . or get away from it?
It can be nearly as agonizing for you as it probably is for the two people on the date.
Here are a few stories shared by waiters who experienced their customers on bad first dates:
“I was working at a Mexican restaurant waiting on a couple and I could tell it was a first date by the questions I heard them asking each other.
Towards the end of their meal there was [a Spanish-speaking] girl sweeping next to their table and the woman looks at her, holds out the remains on her plate and says, ‘would you like to take this home to feed your kids?’ I stood there in complete shock.
This woman spoke no English, but she could tell this random woman was completely degrading her. The sad thing is she seemed like she really thought she was doing a good deed. Her date looked so embarrassed.”
“Once witnessed a date where the dude talked about how special he was and how his mind wasn’t like other people’s for the entire date. The girl was politely nodding along and every time she tried to get a word in, he’d cut her off. Absolutely brutal.”
“I once had a guy come sit at my bar who was waiting for his blind date. He orders a couple of drinks to calm his nerves. Well, he probably should have slowed it down to keep his mouth from working faster than his brain.
She shows up and is waaaaaay out of his league. She is absolutely beautiful. She orders a drink and they start talking. I come back to check on them and I hear him talking about how much he hates children. He was saying things like how he hopes he never has any, and that he will never be stuck taking care of them, and how he wishes that kids couldn’t be taken into public places so that he wouldn’t have to be around them.
She looked him dead in the eye and said, ‘Well I have a daughter, and I love her very much.’ She grabbed her purse and walked out on him. The look on his face was absolutely priceless.”
“I work in an Italian restaurant. A few years ago I waited on a guy and girl who met for the first time at the restaurant. There were awkward pleasantries exchanged at the door and then they were seated.
When I was taking their order the guy asked if we had soup because he had mouth surgery a few days prior and chewing food was still a little rough. We don’t have soup, so I explained that the ‘softest’ food on the menu was gnocchi.
He ordered the house gnocchi and proceeded to cut each tiny dumpling into four or more pieces and slowly chew each piece. He ate that entire dish over a 3 hour period and the girl stuck it out for the whole thing. She looked miserable and I’m pretty sure they never saw each other again.”
How I turned another bad date into an okay date.
The first time I used dating sites, leading up to meeting “Sam”, I made a date with a man whose profile picture didn’t show much of his face.
He had on a baseball cap and big sunglasses. That should have been a tip off. But I was very green then.
We met for lunch, which I learned not to do after that.
He was waiting when I arrived. The baseball cap and sunglasses were off.
He was startlingly unattractive. He must have known this, so he didn’t show his face in his profile photos.
I felt like I’d been tricked, but really it was my own fault for making the date even though his profile photos didn’t show his true self.
Although I never felt my ideal partner needed to be great-looking, I knew I needed to enjoy looking at his face, and he had to be relatively fit and look like he took care of himself. This guy was none of those things.
This was the first date before or since that I felt like running. But I would never hurt someone by abruptly leaving, unless he was a creep or I felt unsafe.
I smiled often and made conversation, but I was probably sending signals that I wasn’t interested. We were both very uncomfortable.
I took a breath and decided I wanted to turn things around.
Then, when there was a painfully long lull in the conversation, I blurted out kindly “This isn’t going very well, is it?”
He chuckled a little and said “No, it sure isn’t.”
We both instantly relaxed and began to have a nice rest of the date. He was a very pleasant man, easy to talk with once we both loosened up and just took this as a date that didn’t work out.
We shared dating horrors and gave each other advice. It all ended very well. We hugged goodbye as friends. I sort of remember him fondly.
Don’t fault me for being superficial and judging him by his looks. That was only part of it. There were too many other things about him that didn’t work for me. And vice versa, I’m sure.
Among other things, he was an avid hunter and gun collector, politically ultra conservative, and we had almost no common interests. He was all around not a good match for me. But I have no doubt he would have made someone else happy.
Lesson learned, or reaffirmed, here. Always be kind, no matter how disappointed you are on a first date. You’ll both leave feeling good about yourselves.
Who knows, you may even connect each other to your ideal partner!
As always, my advice for finding your soulmate is to make a dating game plan and stick to it.
Read more about first dates in Our Best Advice for Better First Dates Over 60.
And learn the ins and outs of online dating in Top 10 Best Online Dating Sites for Over 60: How To Choose and Use Them.
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