Dating a rich guy is very similar, in many ways, to dating a dumb guy. Basically, it’s that same old story –- you probably went out with him because either you thought he was hot, or it was a blind date. Or, possibly, you did the math and figured he could support you while you pretended to have career goals and bought shoes. Sadly, you’ll have no idea the sort of dating horror show you’re starring in until you’ve wasted a few evenings, hoping against hope, that somehow he didn’t really mean to say “This Vietmamese food is delicious” 44 times while eating at the Hong Kong Palace (dumb guy), or that he was joking when he repeatedly claimed that “only communists don’t pronounce the “t” in valet” (dumb guy) …or that his family’s money has not turned him into a raging conservative asshole (rich guy or rich-dumb guy).

Rich-dumb guy

Trust me. I know the story all too well. My rich guy was named David Withersmith III (rhymes with turd), but we’ll call him Barry. He was tall and spindly like a really skinny chair lamp. Only less interesting.

 

 

 

 

 

 

 

 

 

 

 

 

David. I mean Barry. He really did look like this.

We were set up by a mutual friend, a “friend”, by the way, who I have not spoken to since. Apparently Barry had seen me and asked my friend, Jenna (we’ll call her Fat Martha), if he could get my number.
I had just graduated from college and was working at a job that I hated (so very, very much). And with the end of college, my dating life seemed to end as well. It had been 6 full months since my boyfriend and I had broken up and I had yet to go out to dinner with anyone besides my mom and Fat Martha. On top of it all, my college loans were going into repayment. In short, life was pretty terrible. So the idea of going out with some mystery guy sounded like more fun than I’d had the night I watched When Harry Met Sally and ate an entire wheel of parmesan cheese… And then (drunk on salty cheese and bourbon) called my ex and told him he had bad posture and horrible taste in future girlfriends.

Not the easiest cheese to eat in mass quantities. And not really worth it.
According to Fat Martha, Barry was a nice guy. She said he was tall with dark hair and green eyes. She also may have mentioned that his family owned about a dozen or so businesses in the area. This was interesting only because I was so used to dating philosophy majors and musicians, that my dates were generally restricted to Jack in the Box or sitting on someone’s beer-stained sofa with his roommates, playing video games. I was curious what it would be like to go out with someone who had dental insurance, so I gave Martha the okay to pass along my number.

And then he called. To be continued…