Let’s Share Some Of Our Weird Dating Stories

You just can’t make this stuff up about first dates. And I have had front-row seats every day – for the past 27 years.

Today I focus on stories men have told me recently. Why? 40% of my clients are male in their 50s to 80s and they get frustrated too with online dating. Actually, everyone gets disappointed with online dating, that is, until they meet “the one” and suddenly that dating site or app is the best in the world, as they tell all their friends. Over 65% of my clients find long-term relationships but it most certainly is not magical as quirky things can occur along the way.

Keys to Online Dating

One of the keys to online dating is to make sure you are on the right site and that can be no easy feat with over 1400 dating sites out in cyberspace.

Other advice I included in a recent AARP article is “registering on a site that works best for you – not just going with one that your friend used… Don’t pick a site because your best friend in New York chose it and met her boyfriend. You may live in Chicago or Dallas, and the same site can be very different in various parts of the country and not have the same quality of subscribers.”

If you’re intimidated by filling out a profile, ask for help – either run it by a friend whose writing skills you admire or hire a professional writer to assist you – and yes, there are professionals who specialize in writing people’s dating profiles.

To quote myself from same AARP article, “Think of it this way: Before you played golf, you probably had a few lessons. Same with pickleball. Get a pro to write your dating profile, vet your photos, assist with site selection and help you write unique messages. It will save you 80 percent of your time, and you won’t feel like you have a full-time job.”

Back to the Weird Stories

I have plenty of weird dating stories my clients have shared with me. Here is what men have told me about first dates:

Jon, 67, Boulder, CO – Morbid Date

“We had a walk and talk date – I was thrilled because one more sitting-around coffee date was going to put me to sleep. We grabbed coffee and she led me to a cemetery, with headstones going back to the 1800s. Then, she sat down and started sobbing at a random gravestone. I helped her up – only to have her walk ten feet and repeat. Three more times. Too bad she was super cute but on the morbid side.”

Thomas, 55, Las Vega – Unquenchable Appetite

“On our second date, we went to Caesar’s Palace for their amazing upscale buffet. I watched in amazement as she went back three times and loaded up her plate and ate every single bite. Hey, I’m all for eating and this is not a ‘ woman should watch her calories’ kind of thing – I mean, we are at a fancy buffet. But piled high. I mean like double what a plate holds. Then she looked at me and said “What? I just went off Ozempic after losing 75 pounds and my appetite is back. Ready for the dessert table?”.

Atticus, 69, Dallas – Not Putting Time to Be Presentable

“We met for our first date at a high-end wine bar at Preston Center. I knew one of her interests was rodeo and horses. Her first words to me were, “I hope I don’t smell. I just came from the barn.” It was 90 degrees out and she smelled like horse manure. A couple next to us even moved two chairs down the bar.”

Kevin, 70, NYC – Unexpected Encounter

“We met after work for drinks near Times Square. She did warn me, “I’ll be in my work clothes.” I thought it was an odd comment but… whatever. As I was sitting at a high top, a lion (yes, a lion in full makeup) walked over to me and said, ‘Kevin? You look just like your pictures’, and so I had two drinks with an actor in full costume. (Yes, it was Lion King.) I did grab a bit of attention. At the end of the date, she asked me if I wanted a ticket to that evening’s show.”

Michael, 61, Laguna Beach – Lying about Hobbies

“We met for a first date – to go windsurfing. I’m all about the water and her online profile talked about her advanced skills in paddleboarding, wakeboarding, sailing, windsurfing, etc. We rented our windsurfers, headed out, and it quickly became obvious she’d never done this in her life. Her sail was going crazy and suddenly she was swept far away from me – she couldn’t hear my shouted directions any longer. Thankfully, the Coast Guard rescue saw her and towed her back in. I stuck to more conventional first dates for a while after that one.”

So, you see, we women often make fools of ourselves when we go out dating. Be honest in your profile, don’t advertise yourself falsely, and do take some time to prepare for your date. It will be worth it.

Let’s Have a Conversation:

What sort of a first impression do you make on a first date? Have you embellished your online dating profile? Have you ever claimed to love a hobby only to get more interest from men? Do you have any silly dating stories to share of your experience meeting men?

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