Written 10/19/2025.
I promised myself that I would not write about my love life at this point in time other than to say it’s been going amazingly well. I’ve been journaling about it and may turn it into a book with the current working title, “Dating Over 50 - a Man’s Journey.”
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Here are some things I can mention that you may think amusing and for those men who are dating, may want to use yourself.
Google Keep Notes
I keep a google keep file on the person I date. This includes all the important stuff like their kids’ names, ages, likes, dislikes, sizes (if you can), birthdays, favorite drinks, foods, etc. Basically, anything that she talks about that may be relevant in the future. This has been really helpful as my memory isn’t as accessible as it was 20 years ago (I could pretty much remember everything, even if I read it only once in a book). Now, that info is still in my brain, but it takes a little while to percolate out.
Dating Folder on my computer
I keep a folder on my computer which includes things I’ve generated for a date. I have a curated list of music venues around Oak Brook, a “dating index cards with questions 2 pager” It lists some questions like “if you could hop on a plane tomorrow, where would you go?” It talks about dropping soft compliments such as “You’re really easy to talk to - I like this.” The card also mentions paying attention to how she mirrors my energy. Since this is an index card, I can keep it in my pocket and glance at it to make sure I’m on track.
This may sound funny, but when you don’t know what the f*ck you’re doing, it really helps.
I have another index card filled with topic specific compliments. Topics include appearance, personality focused, and playful teasing.
Honestly, if I can’t give an honest compliment, I don’t. The good news is that with time and more dates, I’ve gotten better at dropping nice and flirty truthful compliments.
ChatGPT
I use a paid version of ChatGPT to plan dates, especially in areas I don’t know. For example, “places playing music Friday night in Barrington.” I take the results, actually research them as more than 50% are wrong, and create my curated list and choose one for the date.
I have also used ChatGPT for first date, second date, and third date suggestions. Usually, I try to put in the personality of the person and ask for recommendations from what to do, how to interact, e.g. should I go in for a kiss goodnight, etc.
Once, I took a whole text thread from a woman, downloaded it, stripped out any identifying information due to privacy concerns, and asked ChatGPT to tell me about the person, what’s important to her, and how I should interact with her. I already had my ideas, but it’s nice to both get confirmation and see whether there was anything I missed.
Wing Women
I have three different women I bounce ideas off of who have been life savers, preventing me from screwing up. They also interpret the signs I totally miss from my dates when I tell them about what happened and the interactions.
For example, I’ve seen the memes where a couple go into a thrift store and buy each other clothes that they have to wear for a date night. Next, I was part of a scavenger hunt where the losers had to wear funny T-Shirts from the store 5-Below. Combining the two together, I got it on the brain that wouldn’t it be fun to buy 4 funny T-shirts from 5-Below and allow my date to pick one, open it up and then decide whether she was going to wear it, or give it to me to wear. If she gave it to me, then the next shirt she picked she’d have to wear for our date.
I thought this was a really cool and fun date night idea. Then I passed it by WW (Wing Woman) Susan, who replied, “oooh, no. Don’t do that.” She proceeded to tell me that women take time and effort to pick out the clothes they wear for dates, and this would basically be a slap in the face.
I didn’t do it, but I did float the idea past one of my dates (because I still thought it a cool idea). Let’s just say that WW Susan was absolutely correct.
Summary
So that’s what I’ve used to try to learn about this weird, wonderful, roller-coaster world of dating. If you have any suggestions THAT YOU HAVE USED that have been successful, please send them my way. I’ll may try them and put them in my book.
As always, I love each and every one of you.
Robert
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