I had my first date off of the Facebook Dating App...it went well

Photo by Cezar Sampaio on Unsplash

Written 8/16/2025

If you’ve read my posts, I decided to try the FB dating app to get practice with both texting/flirting and dating. I’ve matched with more than a dozen women and chatted with over half of them (even if you match, meaning they liked you too, some never respond). Some fizzled immediately, three were interesting enough that I asked them to be taken offline.

The first person actually asked me to chat over the phone. That was over a week ago and we’ve texted but haven’t talked. I asked to talk to her tomorrow. She’s the one I have the strongest connection to. That said, there are some things she hasn’t worked out in her life that may be a problem. Still, I’ve had a lot of fun texting with her.

The other two I asked to meet. Both said yes and the first was this morning. She lives around 30 minutes away and I gave her a couple of choices from coffee, coffee-walk, or hike. She chose hike (she’s also a big runner, runs 4 miles 5 or 6 times a week). She wanted me to arrange it, which I was happy to do (it’s a common test women give men. If a guy can’t even handle arranging a date, then it’s not worth pursuing him. I agree).

ChatGPT came to the rescue. I asked about hiking around her area, and it gave me two options, neither of which I liked. I looked at the map and found what looked like a much better place. I asked ChatGPT about it and it gave me a run down. Then I looked at the website. It was a nice place with a nature center and couple miles of hiking trails around a lake.

I then asked my date what her coffee order was. Small coffee, light cream, sugar. No dietary restrictions. She was really happy that I had arranged something quickly, that I let her know, I and was going to get her coffee (we met at 9 am).

She said she wanted to get sweets and bring water. I opted for a scone.

We met and sat and ate. Walked through the nature center and went for a hike. She was amazingly easy to talk to and 2 1/2 hours flew by. I don’t think there was a “OMG this is it spark” but I’d be very happy spending the day or even travelling with her (she’s been around the world). I’d definitely chalk this first date as a success in compatibility. She is 3 years older than me, but age doesn’t bother me too much either way. She was nice and kind and we talked about a variety of subjects.

It was nice meeting a person for the first time and it turning out well.

I’m going to try to meet the other two next weekend as my daughter will be back in school and my brother is scheduled to visit my parents that weekend.

Note, I still need to be better about flirty texts and saying flirty things. This was ripped out of me by my former wife. Every time I said something flirty/sexy, she got offended and thought I was treating her like a piece of meat. So, I stopped saying anything flirty/sexy. I’m in the process of retraining myself. To date, it’s been harder than I thought it would be. I have a lot of shit in my brain that needs to be thrown out. I’m working to do just that.

If you have any tips, I’d love to hear them.

Blessings to you all.

Robert