I recently joined a Club in Chicago to up my game. This Club is a Restaurant and Lounge and is members only. I feel it will be a great way to meet new people and this has already proven to be true.
Recently, they had a “meet and greet” night for members. I went there an hour before my friend purposely so I could meet new people on my own. I like to do things that are a bit uncomfortable. As if y’all didn’t already know that.
I post up at the bar and meet this guy sitting next to me. We will call him Tom. Tom tells me he lives around the corner and joined the Club to also meet new people. He said he has been retired since he was in his mid-50’s and is currently the same age as The Golden Bachelor. Speaking my language.
Naturally, I now know he is 72 years old. I am of course watching The Golden Bachelor.
He also said he was a CFO of a Chicago company when he was working and now he spends his time traveling and he also sits on the Board of a company to keep busy.
He was somewhat leading with his money. He said he has a place in Michigan and takes a boat back and forth between Chicago and Michigan. He also told me he is divorced twice and back on the dating scene.
He asked if I was on any dating apps (um, have we met?). Of course, I told him. He said he joined match.com and has had 28 first dates and none of them were converted to a second date.
An interesting fact to share. And not that flattering to say to someone he doesn't know very well. Now, I am not interested in ‘ol Tom but from my experience, he was driving to the hoop with me. He was seeing if there was anything I would “bite” on. I did not.
After talking for about an hour, he said he had to run to go to a dinner reservation. I said no problem and will see him at the Club again.
Now, I also have a dinner reservation that night with two of my friends at Hugo’s Frog Bar. I join my friends and we are having a great Friday night.
About midway through dinner, I look around the restaurant and who do I spot? You guessed it, Tom sitting with three ladies at dinner. Three of them! Since he said he didn’t have a second date with the 28 ladies, I am assuming these are numbers 29, 30 and 31. LOL!
When he gets up to leave, I say, hey Tom! He said, Sue, I can’t believe it. What a small world. He comes over to chat and one of the ladies joins along with him. I could tell she was very interested in what was happening and clearly marking her territory. Just in case there was any funny business.
She asks me if I had received the latest notice on some Club rules? I said I did, are you a member as well? She said no, we are members, Tom and me. She “we’d” me a couple more times during the conversation. Just to be sure I understood.
‘Ol Tom is lucky I didn’t call him out on anything. Can you imagine? This guy making it seem like he is foot loose and fancy free when all along he has a plus one. Ridiculous!
Lesson Learned? Players gonna play. He is still running games at 72 years old. I guess old habits die hard. I can’t wait until I see him again as I have questions.
And, a different lesson he told me, have a game plan when you retire. He said if you don’t have a plan, you will feel lost and miserable! Or, better yet, wait to retire. He said the 50’s was far too young, and he regrets it.
Comments