Small World

Cougar Dating

Everyone has that moment, usually once every couple months, where they meet a new person through work, by chance, or random social settings and they find out that have mutual friends or acquaintances. The following story is about a date I went on a few weeks ago with a woman who had the wrong mutual acquaintance.

It all started on Bumble where I met this older woman (44) who had a thriving financial business and a young kid who was looking for a little excitement as a single mother (enter yours’ truly). She said all the right things and she open-minded enough to look past the obvious hurdles with age, professional goals, etc., etc. She’d send happy (G-rated pictures) every few dates and insist on hanging out.

The big issue was (aside from the fact that she had a kid) she lived in Baltimore and driving an hour for a chick I was certain wouldn’t put out on the first date really didn’t seem like the best idea at the time. So we continued to text and flirt and pretend that I was going to make the effort to visit her.

Finally, Debbie (not her name) hits me up and says she’s going to be on business at a gala for work in Georgetown. Hooray! I get to go to the most expensive part of the city to try to woo a chick with her own money back to my house. Sounds exciting, right? Wrong.

We meet at a bar I’d previously met a girl at (because I don’t know DC and it seemed safe) for drinks after we were both off work or whatever. The talk starts out nice and not awkward and we discuss our love for the sport of tennis until I get bored and flip the script asking about her recent dating experiences.

This is always fun for me because I have so many unfortunate tales added to my still fairly recent breakup that garners all sorts of sympathy that make any bland conversation worthwhile. She tells me how she’s been the cougar a few times and gone out with younger men for the thrill of it. She talks about how she met one guy in Baltimore with so many mutual contacts that it just got awkward no matter how much she wanted to bone him.

Then things got interesting. I told Debbie where I was from and my immediate family and all the fun dynamics that make us your typical modern family. Then she asked if I knew some people from my home (and I know everyone) because she did some work with a particular woman in her field including a speaking engagement while trying to hire this woman away from her job at that time. Then she says the name.

Debbie knew my Dad’s fiancee and knew of my father. She didn’t have any specific knowledge of their relationship but knew his name and seemed to be very familiar with her. I was blown away. Do I laugh? Do I drop the mic and walk off? No. I get a few more drinks. She pays the bill. We make out till her car arrives. And I never contact her again.

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One thought on “Small World

  1. jillsadventuresindating says:

    😂😂😂 Happened to me with a guy after a date. Did a Facebook search after the date (this was an amateur move on my part having not done it before). I immediately knew all the guys from a Wedding picture that was his cover photo… Plus one mutual friend… My ex husband!

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