He Was Rich, Rude, and Weirdly Unforgettable

Welcome to Friends and Benefits. Follow our new sex and relationships columnist into the lives and psyches of men and women, young and old, gorgeous and tragic, divine and insane. All names and identifying details have been changed to protect the privacy of the bachelors in question.

“Actually, a lot of the assholes I know are gentlemen. Or vice versa. Dickheads with a family crest and a prep-school code of honor.” —Jay McInerney, Story of My Life

I was 27. I had quit my corporate job and moved in with my aunt in New York. She wasn’t in town much anyway. I started writing all day. I made no money. I didn’t have a boyfriend.

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