A Look into the Filthy Rich Guide |

I used to be really rich. I made a lot of money on Wall Street, got addicted to coke, lost most of it… Oddly, that’s the best thing that ever happened to me, and it also means I have a unique window into how wealth makes people act really weird. It’s primarily the reason I was asked to be one of the commentators on The Filthy Rich Guide airing on CNBC. I digress…

Everyone is on their best behavior during a first date—well, at least they should be. Even through the second date charade we only show our best selves, but it’s also a time to offer a tiny glimpse of who we really are. Back in 2004, I’d just had a fantastic first with a girl named Jenn. She looked exactly like, say, a backup singer for Enrique Iglesias would—maybe because she was.

We’d gone to a margarita-infused dinner in Nolita on a blind date and the night ended with a kiss on the cheek. So I called Jenn to see if she might want to come over to my place for a followup. She said yes.

It was a bitterly cold Saturday night in February. The fireplace was crackling in my 2,700 square-foot triplex apartment in TriBeCa. Okay, so maybe I had a leg up. But the setting doesn’t impact this story, promise. The plan was simple: Jenn would come over; we’d hang out and drink some wine, order Italian food (her favorite, which also proved I was listening on the first date), and then cozy up on the couch and watch a movie. And it was all working. The Duraflame went against my Maine upbringing but perfectly set the mood, the food and wine were exquisite, and the conversation was effortless. I was thinking, “I’m the man!”