WOMEN
08/28/2015 09:21 am ET

Searching For Sugar Daddy

Do you ever see a super-old, super-rich guy out on the town with a super-young girl who's super out of his league and wonder, how the hell did that happen? This is how it happened. Taffy Brodesser-Akner investigates the bold new transactional-love economy

1. THURSTON VON MONEYBAGS

Thurston Von Moneybags (not his real name) was scammed once by a girl in Houston. He had arranged to meet her so that he might size her up and determine whether he wanted to give her a monthly stipend in exchange for regular sex and sometimes maybe dinner. In other words: Was there chemistry? Was she blonde and blue-eyed, the way he liked them? Was she thin “but not anorexic, a shapely body, you know?” Could he talk to her? That was very important. It was a little important. It wasn't that important. Anyway, she asked for money up front, and he sent her $800. She didn't show to the meet, and that's the last time Thurston Von Moneybags ever got hustled again. Now he meets the girls for lunch before he offers them an ahem arrangement, and he is very clear. He doesn't give them money until their second date, when they're in the bedroom, which sometimes feels bad, which sometimes chips away at his this-isn't-prostitution line—Thurston was raised Catholic, after all—but what's the alternative? Getting scammed again? I don't think so. A thing you should know is that there are very few people to root for in this story.

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