A Cougar’s Guide to Chicago

Episode II: Cougar vs. Sugar Daddy

Autumn leaves have officially arrived with the blessing of the college football season and a new crop of tadpoles rooting for their alma mater universities. With some sentimental feelings, the change of season leads me to muse over this past summer’s events and, oddly enough, my encounters with Sugar Daddies. Being an “official” Cougar on the prowl, it seems out of the ordinary that I would have any interaction with Sugar Daddies. But I did this summer.

Cougars and Sugar Daddies have an odd relationship. As a young Puma (Cougars in the making in their 20s and early 30s), I often had encounters with Sugar Daddies who would try to ply me with drinks and take me to the trendiest restaurants in Chicago. Sometimes, I would take them up on their offers, sometimes not. As all good Cougars know, a drink offer from a Sugar Daddy means you get my attention for a moment in time, but not much more.

Once I got to a certain age and entered into my Cougar years, my encounters with Sugar Daddies got less and less frequent. I know to avoid their official safari, Chicago’s “Viagra Triangle” (Rush and Division) for gold-diggers. For the most part, I have steered clear of Viagra Triangle to protect my street cred and because what would be the point? It’s general knowledge that Cougars and Sugar Daddies do not date.

So it’s surprising to think I would agree to go out on a date with previously mentioned man of a certain age. It was a blind date of sorts where a friendly acquaintance knew of a great guy who just moved here from San Francisco and would I be interested in meeting him out for a drink. Never one to pass up a good opportunity and playing the odds, game on. The Blind Date (BD) was a marketing executive for a local media company. We exchanged text messages and he offered take me to a concert, two hours before it started, where he had backstage passes. When that didn’t work out we agreed to meet up for a drink. I had suggested Bin 36 and he countered with Hub 51, which had just opened up this summer in the River North area of the City.

I put on my Club Monoco spaghetti-strapped, black dress with a flounced hemline, heels and cabbed it to Hub 51. BD’s physical description was early 40s, 6’1″ (I’m a sucker for tall guys) with floppy, sandy blond hair and an “athletic” build. For a Tuesday night, Hub 51 was mostly packed in the bar area and halfway full in the restaurant. It was a young scene. Maybe it was the rich, dark colors of the décor or the special lighting, but my interest was piqued because the attractiveness level of the crowd was high. Definitely a scene and be scene place. Plus, I spotted a few groups of tadpoles!

Slightly peeved because I didn’t recognize anyone who resembled BD in the crowd, based on his physical description, I texted him. BD responded he was there! Scanning the crowd in the bar area, I didn’t see anyone who resembled his description until I stopped in my tracks and saw a portly gentleman who was definitely not athletic, with a crew cut and dressed in tailored suit. He waved over to me. My first reaction was to ignore him and walk out, but my mother raised a very polite girl!

It was BD in all of his glorious Sugar Daddiness. He was actually quite personable and we chit-chatted about his thoughts on Chicago and did a comparison of Chicago versus San Francisco. A very friendly waitress came around and took our order of crab nachos, a split of White Star bubbly for me and a beer for him. The drink selection at Hub 51 is quite good with something for everyone, but I’m still not quite sure what to make of it with its posh décor and drinks with bar food aspiring to be gourmet and Sports Center on TV. After observing that I was sipping my last drops of the White Star, BD asked me if I wanted to go back to his place to sample some wine from his cellar. Ahem, he was very nice, but I politely declined. We hugged and parted on friendly terms. Very adult and mature as the people we are.

Episode I: an Introduction and Kirkwood Bar & Grill

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