Why I Won’t Date Successful Men Anymore

Christina Holland
4 min readApr 13, 2017

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Inspired by Why I Won’t Date Hot Women Anymore

When it came to dating in San Francisco as a 30-something hot woman, Stella Kombucha had no problem snagging the city’s most financially successful men.

“I could have anyone I wanted,” said Kombucha, a woman with hair, as well as the correct number of fingers and toes. “I met some nice guys, but mostly I went for guys who had a very high — bordering on delusional — opinion of their career success and appeal to the opposite sex.”

She dated private equity guys, tech bros, and venture capitalists, all of whom made very impressive arm candy at social events, but eventually she got tired of them constantly talking about how they were mentioned in a blog or how Bitcoin was going to be the next great thing.

“I couldn’t get through a dinner date with them without them challenging another diner, or the waiter, to a fight and asking them if they even lifted, bro,” she says. “It was embarrassing. Most of the time, they didn’t even lift themselves.”

According to new research, Kombucha’s right about men who are proud of being more successful and appealing than they actually are. A new study from Stanford shows that the more expensive a suit a man wears to work, the more likely he is to put a phone conversation on hold to jerk off. At the high end of suit prices, test subjects would actually tell the caller this is why they were putting them on hold.

The study also looked at men in high-paying executive roles who regularly wore cargo shorts to work, and found similar results, except they would more often put people on hold to “practice their daily kata” with a “genuine samurai sword”.

There were even more interesting findings for men who wore both suits and cargo shorts simultaneously.

After hearing 20 recitals of the lineage of her date’s samurai sword and how hedge fund traders like him were, in a way, the modern day extension of the samurai tradition, Kombucha decided to bail out.

Her current husband Ed, a manager of a Whole Foods franchise, may not be the kind of world-shaking business titan she used to date, but she was totally okay with lowering her standards for him.

“He tries very hard,” she said generously. “I actually really like the way he never talks for three hours about that one time 5 years ago he made a killing on exchange rates. I mean, of course it’s because he doesn’t know what exchange rates are, but that’s okay. Not everyone can be good at everything. I’m okay to being married to someone who I don’t really consider the best, but somewhere in the 70th percentile, because he has other qualities, probably.”

Ed, who had been present at the interview up to that point, suddenly got up and said he had to go do something in the next room, and that he had something in his eye.

Kombucha went on. “I mean, look at me. I have all my organs, 20/20 vision, no outstanding debt, and have completed college. I’m entitled to any man I want — Vin Diesel, Mark Zuckerberg, Tom Brady, Alan Rickman— oh, is he dead? Well, he would probably come back to life if he knew about my perfect attributes. But I chose Ed, and you know why? Because he won’t talk my ear off about how winning the stock market is just a matter of “basic game theory” and “knowing how psychology really works” and how he’s got a system.”

Even some successful men admit there may be drawbacks to dating them. “Sometimes being near so much raw power can be dangerous,” said Travis Kalejuice, a hedge fund trader turned venture capitalist, lifting his shirt to reveal his abs. “You see this? I could accidentally rip a woman in half during lovemaking. I know I look like I was born a perfect Adonis, but believe it or not, this comes from me putting in 6 days a week at the gym. The seventh day? Rock climbing. That’s the kind of mentality you have to have in this business. You don’t quit. You don’t take a day off. It’s like the ancient samurai. They had a code. They didn’t worry about work-life balance. They didn’t worry about “self-care”. Their secret was total focus. That’s why I keep a samurai sword, to remind me of the code, which I myself adhere to religiously. This sword is actually 500 years old and was gifted to me by a descendant of the original swordsmith. I train with it every day after the gym, and I bring it rock climbing. It’s important to adopt wisdom and ideas from other cultures. That’s why I’ve learned 10 languages and I encourage my staff to learn them too. To motivate them, I write all my executive memos in kanji. And of course there’s more to culture than language. I’m also learning to play the erhu, which is the Chinese violin. A lot of men can play Western instruments and that’s impressive I guess, but how many executives do you know that play the erhu? I bet you didn’t even know what an erhu was. That’s an erhu right there, by the bonsai garden. You mind if I play you a few bars?”

He started to play Stairway to Heaven on the erhu and then stopped. “I’m so sorry, I always get carried away talking about interesting subjects like my interest and expertise in other cultures. You were asking about women. Most women can’t really handle me. It’s true, I can be tough to date. That’s the downside of being so intelligent and complex I guess.”

Stella Kombucha agrees. “I’m really glad I don’t date men like that anymore. Mediocre men are so much easier to get along with.” As the faint sound of sobbing came from the next room, she added, “I’m really glad I settled.”

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Christina Holland

I’m not sure what kind of stuff I’m supposed to put on this website