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Is She Hot? Are You Rich?
  • May 30, 2013 : 07:05
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I live in Los Angeles, which means most of my single guy friends think they should be dating a model or an actress, or someone who looks like a model or an actress. Who can blame them? The most gorgeous girls from all over the world arrive every day, hoping to make it in Hollywood. They might end up as waitresses, but they’re still here.

When these guys ask me to set them up, I tell them I know women who are smart and successful but civilian attractive rather than professionally hot. This rarely interests the bachelors even though I’ve successfully set up three marriages, with a fourth on deck. Sure, these guys married pretty girls, but the women had a lot more to offer than good looks.

You can ask for smart and funny and get hot as a bonus. But if you ask for just hot, that’s usually all you get. Plus, I don’t really know women who are just hot. Why would I want them around?

A few years ago I tried to set up one of my eligible Hollywood friends with a fun, smart, skinny blonde. He insisted on seeing a picture of her before he’d agree to a date. I had only a mediocre iPhone photo to e-mail. (I have other things to do besides play matchmaker. Honest.)

He thought she wasn’t hot enough, probably because he’s used to getting professional head shots when he makes this request. A mutual friend clued the blonde in on what happened. When my Hollywood friend finally met her and realized she was definitely pretty, it was too late. She wasn’t interested. He’s still single.

If you go for a girl just because she’s hot, you’ll learn what it feels like when a girl goes for a guy just because he’s rich. Yes, it’s time for the classic role reversal. You’re a good guy, a hard worker, your mom thinks you’re handsome. But your wallet? It’s just average size. And now that nice girl you’ve just met looks through you as if you’re invisible. How does it feel?

When I was in my 20s I made that mistake. I dated a Wall Street titan’s son who was very sweet, until I had a terrible reaction to corrective eye surgery. (I thought I was going blind.) He’d never had to take care of anyone before and it freaked him out. This freaked me out enough to cancel our upcoming trip to Aspen. Unfortunately, that was the first and last time I was offered a ride on a private jet, but there’s no bigger turnoff than a man who runs away when you need him most.

Another winner from that decade was a real estate heir who lived on a very high floor of a Trump tower. He loved treating my broke friends to fancy dinners, which I thought they appreciated until they made me choose him or them. Oh, and if I took a cab to his place, he would make me change all my clothes before I could sit on the furniture.

Don’t even get me started on the guy I ditched in St. Barts even though he bought me a Pucci bikini. (He brought his own lounge-chair covers.)

These guys had tons of money, so they didn’t have to develop other qualities that women find appealing in men, like compassion and maturity. It’s the same with hot girls. They can get away with murder. They’re usually late. It takes them forever to get ready and they always wear the wrong shoes for walking any farther than the valet. Those beige stains on your white hand towels? That’s their makeup. You may not have heard of the college they attended. They order expensively, barely eat and don’t even pretend to reach for the bill. They’re always cold, and they get headaches at all the wrong times. You will always have to check baggage when you fly with them.

Remember the hottest girl in high school? What’s she doing now? Probably not much. Maybe she’s married with kids and lives in your hometown, or at least near it. She definitely doesn’t look as good on Facebook as you remember her.

Meanwhile, the nerdy funny girl you didn’t think was pretty enough to take to prom may have a cool career and enough cash to buy a better-looking middle age. Tina Fey was no looker until her 30s, when she lost a ton of weight, got on TV and became wildly successful. Now she looks awesome, thanks to her stylist, trainer and hair and makeup people. Success makes women look better with age.

I’m not saying you need to make an ugly woman your wife. If you’re shooting for a nine or a 10, knock it down to a seven or an eight. You’ll get more value added in other departments.

The girl you think isn’t hot enough to date could turn out to be your best friend and a fantastic mother of your children. Go on a few dates with her even if she’s a size 10. Is your body so perfect? Hang out with her friends. Let her teach you a few things or at least turn you on to some cool new movies and music.

Having sex with the hottest girl in the world is a fun fantasy, but if you actually get her, it will eventually get old. She will snore, fart and complain about what you want to watch on television. And she’ll probably dump you for a richer guy anyway.

read more: Sex and Dating, relationships, dating advice, issue june 2013

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