100 Days of Summer: Jay Michael’s Blog

The new favorite line in every reality TV series these days is “I don’t do shady,” which Hamidah says to Pascale when they meet to “sort out” their issues. As I say in the first episode, I bet these two girls will end up besties … it’s just the way things sometimes happen when two strikingly hot, hard-headed, outspoken women meet, right?

Drawing lines in the sand seems to be our theme this week. Last week’s party at the DouchePen (my eloquent redefinition of the playpen) was all about coy Midwestern politeness, while this week’s White Party was where things started getting authentic. This was not only my first visit to Cuvee, but also the first White Party I can remember attending since college — or perhaps as far back as high school. My read on Pascale when she walked into the party in a striking blue dress was that she had better plans after this shindig. “It’s 1998 and I’m hanging with P. Diddy,” is how she refers to the party — she was 10 years old in 1998.  Meanwhile, the rest of the country sees Chicagoans as people who foolishly dance around a bottle-less table in toga-looking white getups while a few underdressed ladies dance around magnums of champagne … the “San Tropez White Party.” Not very Chicago, not very San Tropez, either.

A few days later, we make our way to the PAWS event at Castaways, which is very Chicago. It should have been focused around Tara’s philanthropic work with animals, but instead, the day ended up being more about Phillips, as I learned why our resident Mensa member won’t allow her adorable dog Nigel Barker out of his carry bag. Our little Nigel spends his days assisting Phillips from a precious fur-lined, mirrored box. If this wasn’t made for TV, what is?

Then begins my terribly awkward date scene. My mother will be proud to know the subject is a handsome, Jewish, former model-turned-doctor. This was date number two, and much to the chagrin of Patti Stanger, we both far surpassed her two-drink rule and my questioning became a sort of an interrogation. Truth be told, Jeff (my date) had come from a boozy event prior and was only downing Manhattans to soothe his gentile Jewish nerves. I mean, he’s not only in front of a camera crew, but being questioned, military-style, by a slightly aggressive, persistent, baby-craving gay … on the second date.  Thankfully, you were all spared from watching the two of us barely get one another into our respective cabs. There wasn’t a third date, but I’ve since set Jeff up with two other doctor friends of mine. Maybe being a Yenta (Yiddish for matchmaker) is my real calling!

By Jay Michael