This past Wednesday, I went to Jazz at Bar Basque with Rachel Hall only to find the band ended it’s set early to celebrate jazz trumpet player Mike Cottone’s birthday. Luckily we were more than thrilled to join the jazzers and their celebration for the evening.

Shortly after we arrived, Rachel’s coworker from Equinox Fitness, Adrienne showed up with several friends of her own. It didn’t take long for me to learn that Adrienne lived across from my favorite piano bar on the East Side, and that her friend Genie and I both befriended the same cross dresser, Karen.

“You do not know Karen!” yelled Genie.

“Karen is great! I love Karen!” I replied when referencing the demure cross dresser who, is actually a straight man who has a full career in finance, but just loves dressing in women’s clothing.

When we realized that Rachel would do much better without us for the evening (she was getting rather close with one of the jazzers), we decided to pay the piano bar a visit and search for Karen. As I crossed the terrace to say my goodbyes, I recognized one of the party guests as a Juilliard composer who I had gone on a date with over a year ago- we’ll call him Jason. Again, let me remind you I’ve lost a bit of weight lately and replaced a lot of fat with a bit of muscle.

“Hi I didn’t get a chance to meet you” said Jason as he shot up to introduce himself as I was about to leave “I’m Jason.”

I extended my hand and said “Hi, my name’s Jacob- I’ve met you before.” He looked dumbstruck as he gently shook his head.

“Um, I’m sure I would remember meeting you” he said with the upmost sincerity. I pulled him close to me and reminded him of our Central Park coffee date the year prior. He then pulled back with an expression that read both “Eureka” and “oh shit”.

“That’s alright” I said with a smirk before walking off to meet Adrienne outside “Have a wonderful evening.”

As we neared the piano bar, Genie decided that she was too tired to join us and went home. Immediately upon stepping inside, I saw Karen sitting quietly by the bar and took Adrienne over to introduce her. Karen instantly took a liking to Adrienne and kept her company while I made a quick phone call.

“Oh my God” said Adrienne when I returned “guess who’s here?”

“Did Genie decide to come out after all?”

“No… better! Alex and Simon from Real Housewives

“You’ve got to be kidding” My eyes must have rolled to the back of my head. Of all people to have a second run-in with, it had to be Alex McCord. The reality television star’s antics both on and off-air had struck a sour chord with me before. Why can’t I run into Bethenny Frankel or someone I actually like? After telling my photo-assistant friend about my Lincoln Center run-in with the “Real Housewife”, I found out that she had the choice to have her infamous photo-shoot hair redone before going to support Ramona Singer at a gala event. She famously made the excuse that she had just come from a photo shoot and didn’t have the ability to fix her hair, but unbeknownst to us, she did have the time and a team of wonderful stylists to fix her up if she wanted.

Being the social butterfly I am, I went over to Alex and Simon and asked “Now aren’t you two going to sing a little duet for us?”

“Oh I can’t sing tonight, I’ve drank and my voice is (insert gagging cough-like sound here) but you can see me tomorrow night at Splash!” said Simon Van Kempen.

“And you Alex?”

“Oh no, umm he’s singing tomorrow night at Splash” replied the Real Housewife to which I replied with a compliment on her hairstyle. She actually did look great in person, and didn’t have the crazy over-volumized hairstyle she was so ridiculed for.

“This is straight out of the shower” replied Alex “I did nothing to it.”

“Well you’re very lucky- I don’t know anyone who can step out of the shower looking like that.” I wasn’t lying, she did look fantastic. After a couple more words, I excused myself and joined Adrienne at the piano before we called it an evening and parted ways.

I will say, the couple was incredibly nice and I did appreciate their ability to socialize with anyone and everyone in the room… including Karen.