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Dear E. Jean: I’m a 34-year-old Internet entrepreneur and angel investor. Can you help me find a woman? What I’m looking for is a life partner— not the “mother of my children.” Anyone who aspires to be a housewife is automatically eliminated. The women I fall for typically intimidate men. I suppose the easiest way to summarize is to say that I’m seeking a smarter, hotter, younger, female version of myself (smile). I’m cognizant of the fact that ultimately I’ll fall in love with the woman and not the checklist. So without further ado, here’s the perfect girl for me:

  • Out-of-this-world intelligent and passionate
  • Ambitious and extremely independent with eclectic and diverse interests
  • Not needy, high-maintenance, jealous, or requiring constant attention (I suppose it goes with “extremely independent,” but it’s worth mentioning)
  • Very adventurous—loves to backpack around China, for example
  • Supersexual and sexually adventurous, multiorgasmic through vaginal sex
  • On the Pill
  • 5'7"–6'1"
  • Very thin (but not because she’s starving herself or has food issues—I want someone who will be thin her entire life)
  • Small breasts (usually come with “very thin”)
  • Gorgeous (symmetrical face and features)
  • Loves big dogs (but not small dogs or cats)
  • Atheist, agnostic, or not religious
  • Happy!
  • Healthy!
  • Nice!
  • Does not want kids in the next five years
  • Is in her twenties
  • Plays tennis very well, helicopter skis, and is dying to learn how to kiteboard
  • Speaks French perfectly
  • Plays video games (maybe I am asking for a bit much here :) )

Historically, the women who’ve been the best girlfriends for me have been entrepreneurs, lawyers, consultants, doctors, bankers, writers, university professors. That’s not to say there aren’t extremely smart, passionate, ambitious girls who are models, work in marketing or PR, or teach K–12, but it’s just less likely. From a looks perspective, I’m pretty agnostic when it comes to hair color, eye color, etc., but I do have very specific tastes: They run to Kate Beckinsale, Diane Kruger, Izabel Goulart, Eva Green, Joanna Krupa, and Odette Annable. I’m also including the pics of my most serious exes so you get a sense of what the girls I really liked look like. Where can I find her? —The Great Gatsby

E. Jean’s note to readers: When I mentioned the “multiorgasmic vaginal sex” requirement to a friend, she said, “Ha, ha, what an asshole.”

“But he’s one of the richest men in New York!” I said. “He has too high an opinion of himself,” she said. “Naw,” I replied. “The man’s simply saying what most men are thinking but are too politically correct to admit.”

Anyway, I’ve met this fellow. After a wild midnight dinner at Cipriani with a half-dozen tech-start-up guys, I vaguely recall asking him what he was “looking for” and promising to “set him up.” Three weeks later he pinged me his list. And now…my answer:

Answer at link.


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