The Case of Priscilla Worthington

I would like to share with you a recent NYC-based dating episode involving a good friend of Penelope’s (not a disguise for Penelope, I swear). This case study is based on the last five months in the dating life of Priscilla Worthington, a good friend of Penelope’s.

I met Priscilla’s new “man” (just wait, you'll see why I question his manhood) a couple of months into their relationship. Let’s call him Mr. Private Equity. He hails from a posh ‘hood in Newport, Rhode Island and collected a degree from HBS along the way (the mention of which, ten years ago, would have impressed me, but now comes across like an admission of HIV+ status).

So, I met Mr. Private Equity randomly when he showed up to collect Priscilla from an impromptu soiree we were enjoying with the Naked Man and another friend at Smith & Wollensky’s, the capitol of steak and testosterone in NYC. Private Equity seemed ill at ease in the environment and hid a bit behind Priscilla’s skirt. I didn’t want to tell her my initial impressions but I suspected Private Equity would have to break up with himself first before he could date anyone seriously, much less Priscilla, a tall Eastern European head turner with a wicked long drive on the golf course.

I held my tongue, recognizing that Penelope is not exactly a role model for healthy or long-term relationships (unless two months counts as “long term,” which sadly it may in NYC, the city of transient emotions and commitments).

I watched and I listened. The courtship progressed. Although he did not golf, he was an avid runner so he was at least health-oriented. Plus, they shared a love of the theater and they had already booked a New Year’s vacation to the Dominican Republic (before any incidence of cholera had been reported).

But then there was the evening we met for a shopping session at Bergdorf’s so she could shop for a “break up dress.” Some of you may be unfamiliar with the term, but a break up dress is the classy yet sexy dress one wears when one suspects one may be on the precipice of a break up. The theory is that he will see what he thinks he is about to discard, begin to drool, lose all sense of reason, be overwhelmed with torrid images of removing the dress and invite her away for a romantic weekend instead of breaking up with her. The ability of a female to cloud a man’s judgment has long been one of the most significant factors in the perpetuation of the human species, trust me.

Then there were more troubling signs: the weekend he disappeared to Alaska for a funeral, followed a few days later by another trip out West for a memorial service during which he remained incommunicado throughout; and his inability to hold his liquor (actually, any liquor). What was emerging was a stark pattern of incompatibility.

Yet it was still a surprise when at the tail end of a girls’ weekend in Palm Beach Mr. Private Equity and Priscilla broke up.

First there was the abrupt email. He sent her a scathingly critical email as we sat at a bar waiting to board our flight back to NYC. I was so stunned when she relayed the contents that I forgot to pay the bill. Fortunately, ten minutes after boarding, JetBlue re-opened the closed gate, delayed our departure and encouraged me to deplane so I could pay the bill (I really hope that $12 in revenue keeps that bar afloat).

One of the many complaints Private Equity leveled was that Priscilla had not given sufficient prior notice of our intended plans to grab a burger at our favorite burger joint upon returning from FL that evening. Not only was he horrified and appalled by the blatant spontaneity of the burger scheme, but he was truly disgusted by her suggestion that she would then meet up with him post-burger and post-wine. “Priscilla,” he responded “that sounds like a booty call.”

Wait, isn’t every American guy’s dream to have some chick call him up for a booty call? Am I missing something?

Despite his behavior, Ms. Worthington remained open-minded and agreed to meet up with Private Equity for dinner the following evening to sort out their misunderstandings. She planned her outfit carefully. Having worn the break up dress one too many times, she deliberately wore pants for this meeting—the denial of calves and flesh, the ultimate insult. I didn’t want to tell her, but she had been wearing the pants all the time, and had been the only one wearing pants.

It’s awful to be dumped, but to be dumped by a guy who is likely gay and constantly has relatives dying in Alaska is particularly harsh.

In retrospect the compromises Ms. Worthington made were too great, but when do we know where to draw the line between acceptable and unacceptable compromises? How do we navigate the grey area? None of us want to grow old alone so compromise seems like an obvious path forward, no? Maybe the fact he did not play golf was not grounds for immediate romantic dismissal, but short of non-negotiable behavior, like physical violence, how does one decide what is grounds for dismissal?

Penelope