My boyfriend during my freshman year of Brown was a 6'5'' black guy from Philly who played power forward on the basketball team. One of the main reasons I was drawn to him was that I knew my parents wouldn’t approve. They are what you might call liberal conservatives: They’re NPR-listening, cultured, Democratic-voting Jews, but my mom doesn’t like women with visible bra straps, and my dad doesn’t feel comfortable around black men.
It didn’t work out with the basketball player and by the time I graduated I was still single. I moved into an apartment in Brooklyn with some roommates, and at night I barhopped with a girlfriend who had guys falling left and right for her because she smoked and knew how to appear disinterested. I threw myself at every 120-pound drummer who gave me a second glance.
This didn’t make for many long-term relationships, but it did help my career: At 22, I got a job writing a weekly column for The New York Press about my dating life. For three years, I chronicled my dates with a string of actors, comedians, screenwriters, journalists, and novelists, who all had one thing in common: None of them had any interest in marrying me. My parents, who still lived in Brooklyn where I’d grown up, read the column religiously and accepted their friends’ jokes with as much humor as they could.
By the time my 29th birthday arrived, I was making a good living writing about sex—two novels, three columns, countless articles—but I didn’t have a boyfriend, and I was afraid when I died my books would be all I’d have left. So I threw myself a birthday party to convince myself that friends were all that really mattered.
A few days before the party, I decided I needed some art for my walls, and a mutual friend suggested I contact a painter he knew named Jack*, who painted Jewish boxers from the 1930s. I imagined him as old and Jewish but when he came to my door with his portfolio and some paintings to lend, I realized he wasn’t either. He looked to be in his late-30s and he was 6'5'', with red hair and tattoos of his own artwork up and down his arms. He was wearing a wide-brimmed tan felt hat that tied with a string to his shirt button, and something about that old-fashioned sensibility excited me.
I found out he wasn’t Jewish but I decided that was OK; he wasn’t husband material. He’d be a hot fling. I invited him to the party but he declined, which was good because I wound up drinking strawberry margaritas all night and getting so drunk that I threw up after my last guest left. When he came to pick up the paintings we went on a long walk. Because I wasn’t thinking of him as a potential mate, I was myself when I was around him, and not so nervous.