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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“Do not confine your children to your own learning, for they were born in another time.”

This is a Hebrew proverb.

How many times have you said, this is the way it is, because that’s the way I was raised.

And did your parents do that to you and their parents to them?

And are circumstances this life different?

My guess is yes.

And so, all learning must be tempered with the realities of today.

Should we be strict?

Or should we be a little bit more flexible?

What are your thoughts?

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“Poor is the man whose pleasures depend on the permission of others.”

- Madonna (singer)

We need to follow our own passions and if people say, “that’s wrong,” well, maybe it’s not.

What are your thoughts?

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“At the feast of ego, everyone leaves hungry.”

This was seen at Bentley’s House of Coffee and Tea in Tucson, Arizona back in 1998.

I saved the quote because it’s a good quote.

What are your thoughts?

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“If you try to be a better dog, sometimes you get an extra cookie.”

Attributed to Snoopy, even though I’ve never heard Snoopy talk.

But I like the sentiment.

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Written 10/14/2025.

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I got the call at 10:30 am Friday morning. I had dropped Hyundai Elantra off the night before and they gave me a loaner car for the day. $2,100 to fix all the brake problems and master cylinder. The car is worth $1,800 at best. If I got it fixed, something else would have broken.

I told them to put it back together. I wasn’t fixing it. Time to get another car. I needed a car for Saturday.

I knew that I wanted one of three brands, Honda, Toyota, or Subaru. All rated highly. Next, I didn’t want to spend much money right now, so I set the results at cars costing $10,000 or less.

Subarus turned up, but very few other cars.

I set the bar higher, $15,000 and got some good results. I also sorted based upon the best deals (vehicle offered below market rate) and found a Subaru that was interesting. I called on it. It was available, but someone was test driving it. I told the salesperson to let me know if it sold.

Next, I put that make/model of Subaru into ChatGPT. It returned stats on typical issues with that particular make/model and repair score. The repair score was average, and I was looking for better (equaling lower repairs).

I put in about 4 other cars, including a BMW SUV (bad repair score - repairs + cost to fix) and finally settled on a Honda Pilot. Mileage was over 100K, but Hondas will go for at least 200K miles. Everything else looked really good, including what chatgpt returned on repair scores and possible issues.

I called the place where the car was being offered and talked to Jim. I asked whether he could go lower on the price it had been on the lot for 99 days. We had a brisk discussion. I also asked about financing, which he replied he had several options.

I went to his website and put my information in to get financing options from the dealership.

I then went online to look at other financing options. PNC bank supposedly had something. I called and had to go into a branch and scheduled an appointment for 2:30 pm at the local branch. I told the person on the phone before we booked the appointed specifically about the car, year, mileage, where it was being sold.

I got to the branch and the person I was supposed to meet with wasn’t there. Another person helped me, which was good. The biggest issue was that they wouldn’t finance a car with more than 85,000 miles on it. So, because the PNC lady who set up the appointment didn’t know it meant that I had wasted over 2 hours of time.

Jim called and told me I was approved to finance all of it (no money down) for 48 months and that since I did that, he’d hold the car for me to see it and start the paperwork.

Off I went in the loaner car. I toyed with taking an Uber over but decided against it in case the car was a dud. It took about an hour to get to Crestwood on a Friday afternoon.

I looked at the car. Seats and interior were pristine for being 8 years old. The exterior had some scratches, and the back cargo area had scratches, but that was to be expected.

The car drove really well; everything worked and seems tight. I inspected the engine, underbody, tires, etc. All looked good.

I went into Jim and he had already done the paperwork for me. He kicked the current family out of his office (they were still trying to decide) and I signed 8 pages and grabbed a key. He kept the other key because he had to move the car to a part of the lot I could access after they had closed.

I also asked him to fill up the tank before I returned, which he agreed to do.

Back to Naperville.

My Hyundai was ready to be picked up. I paid via the phone and brought my extra set of keys because it was after 6 pm by the time I arrived. I had also made an appointment over at Hyundai to sell my car to them.

I brought 2 big boxes to clear all the s**t I had accumulated and dropped off the loaner car and picked mine up. The brakes were very iffy (I had to push close to the floorboard before I’d stop), but I made it over to the dealership.

The guy offered me $500, I countered with $1000. He said he had to talk with his manager, so went off to do so. I waited 2 minutes and walked into the manager’s office and exclaimed, “are you gonna give it to me (the $1000)?” The manager replied he could do $800, no more. I pushed but he wouldn’t budge, and I did NOT want to bring the car come, so I counted with $800 and a Lyft ride to Crestwood. He asked how much that’d be and I said $45. He said okay. So off I went to Crestwood to pick up my car with my 2 big boxes of crap.

The good news is that while cleaning my car out, I found one set of keys that had been missing for about 8 years and another set of USPS keys that didn’t go to anything.

I got my Honda in Crestwood and arrived home about 8:30 pm. I lost a day, but it was just one day, and I really love the car. It’s the first one for me with a backup camera. That is something I’m still getting used to. Oh, and it has a remote starter! How cool is that.

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“The universe only has one effective weapon, and that is laughter” - Mark Twain.

Laughter diffuses some of the fiercest conflicts.

Have you ever had it where you’re just head-to-head and suddenly somebody says something and everybody breaks up laughing?

Let me know.

What was it?

How did that happen?

And how can we do more of it?

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“For man plans, but God arranges.” - Thomas a’ Kempis

How many times have you made extensive plans, and they go a little bit differently?

Do you allow the universe to unfold?

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Do you allow it to unfold the way it should?

Or do you force things?

And what have been the results?

Let me know.

Written 10/9/2025.

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I’ve been meaning to write this post every time I hop on my motorcycle to go for a ride. The brake lever wobbles, there are sounds under the carriage of the motorcycle when I go over a bump. My head gets buffeted when I ride fast causing me to not see as clearly as a person behind a windshield on a car.

Oh, and shifting is different too. It isn’t always smooth, and you can only find neutral easily when you are shifting between 1st and 2nd gear while accelerating in traffic causing an engine rev until you shift again (shifting on a motorcycle is 1st, neutral, 2nd, 3rd, 4th, 5th, 6th).

Let’s talk about comfort. A motorcycle is not your couch or car seat. You have to hold yourself up and your feet hit the pegs wherever that is. If you have long legs, your knees will be higher. You are the adjustment; nothing adjusts on a motorcycle. You may be a little uncomfortable riding.

Next, you are literally sitting on top of an engine and exhaust that gets really hot. If you don’t pay attention, you’ll burn your pants along with your skin if you accidentally put your leg on either. That also goes for your boots.

Depending on the style of motorcycle depends on where your hands are. Imagine holding your arms straight in front of you for hours at a time (cruiser) or handlebars below you as you crouch over them (sport bike - aka crotch rocket).

Then there is braking. Front brake is with the right hand; rear brake is with the right foot. Seventy percent of the stopping power is with the front brake. Motorcycles also stop slower than regular cars.

So pretty much if you are looking for a perfect, smooth, ride, don’t go with a motorcycle. You have relax into the rawness that is riding. If you are willing to do this, then you will experience something very few do. An exhilaration that wipes away the worries of the day. For military veterans with PTSD, a momentary respite from the crap that they constantly experience. Motorcycles have saved lives, many of them due to helping with mental health.

Are they more dangerous than cars? Of course. Everything in life is risky though. There is a 100% chance of death from being born. Fifty percent of marriages end in divorce. It’s part of life. Wouldn’t you rather take a risk doing something you love than never feel the exhilaration? I would and have.

Life isn’t perfect and motorcycles are a reflection of this. If you relax into this imperfection, you will experience a joy few perfectionists ever feel. Enjoy the roller coaster of life. Squeeze every ounce of living from this wonderful world. You’ll be glad you did.

Always remember, I love you.

Robert

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“Yes, there is nirvana. It is leading your sheep to a green pasture and in putting your child to sleep and in writing the last line of your poem.”

Khalil Gibran

The kingdom is beside you is a Biblical quote similar to the quote above.

Do you think so?

And if not, how do you uncover what truly gives you peace and love and joy and spiritual fulfillment?

Let me know what you’ve done.

Thanks.

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