50 M4F We peaked as a society in the 90s #chicago #illinois
You really can’t deny it, can you?
If you …
* Spent your Friday evenings at Blockbuster Video looking for movies to rent
* Shopped at Sam Goody’s, Walden Books, Merry Go Round at the mall
* Lined up to buy a CD
* Had a favorite Trapper Keeper
* Covered your textbooks in paper bags
* Played four square on the playground
* Got your news from MTV with Kurt Loder and Tabitha Soren
… then you may have had the greatest childhood!
Today, I am a 50 year old married white collar male with kids. I live outside of Chicago and work in the Loop. I enjoy traveling, both to new and old locations. I’m looking for someone that works in or near the Loop, and is open to spontaneous (and planned) lunch or coffee dates and the occasional happy hours after work.
I enjoy chatting either over a coffee, beer, or cocktail. In my career, I’ve learned, personal relationships matter. I’m flirty and seek banter through my day and evening. I want to hear about your day.
My OPSEC is tight and would expect yours to be as well. I have the financial cover to run a relationship like this and would expect you to as well.
If you made it this far, what was your favorite Trapper Keeper in the fourth grade and why was it a Lisa Frank?
Posted Apr 2, 2026, 10:46 PM UTC