Pros and Cons of Dating: Old Money

by Allison Davis

Pro: Saying, “Oh, he’s an heir,” really doesn’t get old when people ask what your boyfriend does for a living.

Con: This does not make you an heiress.

Pro: Rich people smell really good. I have no idea why. Lots of free time to shower? Ability to afford expensive scented products from Paris? Evolution? I don’t make the rules.

Con: You know how rich people stay rich? They invest. That means YOU are an investment, and they’re looking for a return on that investment. This means you have to keep your shit tight: manicures, pedicures, waxing, hair done, bikini body, etc. There’s no day off. You start slacking and Ugg it up, and he’s reflecting on that beluga lunch, thinking, I am NOT getting my money’s worth.

Con: They’re constantly questioning if you’re only with them for their money, and will be regularly testing you and/or get super weird every once in a while and not talk to you until you pay them back for that Sprite that one time.

Pro: You’ll need to go shopping for all of the new affairs and soirees you’re expected to attend! Garden Parties, Charity Balls, Fundraisers, Yacht Club Things, Cotillions, etc. This potentially means gowns, elbow length gloves, cigarette holders, jodhpurs, and maybe even a tiara! Right?

Con: Are you up on your rich people manners? As Leon Phelps says, do you know which fork you use to the eat soup? Or how to elegantly fart at a cocktail party? There are rules.

Pro: After a lifetime of attending the best schools, summering at the most exclusive beaches, and a solid trust fund, wealthy people generally have a fairly sunny outlook on life.

Con: Unless they have some weird family secret or dynamic that keeps everybody miserable forever. If they do, it probably involves excessive amounts of cocaine, Cape Cod, and an uncle who no one talks about. You don’t get rich without dropping a scandal here and there.

Pro: They mysteriously always have the appropriate drug (Xanex for long flights, Vicodin when you sprain your ankle) no matter the occasion.

Con: Living in a world without consequences means that they may well have a very, very bad drug habit that you won’t learn about until you’ve been dating for a year and he asks to borrow your car one day, and then crashes it into Safeway.

Con: There is never a right time to break up. Between Valentine’s Day, your birthday, and the holidays, there’s always a reason to hold on for another three months or so to see if things get better. And to see if he gets you that tennis bracelet you’ve had your eye on.

Pro: If you live in California, and you marry him, and then you divorce him, you get HALF. HAAAALLLLLFFFFF. It’s almost worth suggesting that you hear Paso Robles is nice this time of year.

Con: Four words: Pre. Nup. Aw. Kward.

Previously: The Pros and Cons of Dating Your Foreign Language Instructor.

Allison Davis is a writer and TV producer living in San Francisco.

Photo via Belisi