#4) The Lesbian Handbook

“Sex and the City” Season 2

As I was gearing up to turn Straight to Gay from a concept to a reality, I had dinner with my children, and filled them in on my plan. After we ordered wine, I asked my daughter to take the photo that is now my avatar. We discussed some of my exes and topics I would be exploring, and when prompted, both agreed that their favorite of my girlfriends was Jenny. I was surprised because we dated so long ago—back in 2007, when they were only 6 and 9 years-old! There were so many lessons from my time with Jenny, who in many ways was my first grown-up relationship with a woman.

I joked with Jenny that she was my first career lesbian (I know, I love the jargon), meaning she had dated women all her life—with one small exception: she slept with men in between meaningful relationships with women. She mused that the sex was like sorbet between courses.  Unlike most of the other women I have dated from red Southern states, Jenny was completely comfortable with her sexual identity. That comfort in her own skin was one of the reasons my kids adored her—it can be hard to find, but if you do, place it in the plus column!

Jenny was an art dealer who lived in Chelsea, and for our first date she agreed to drive up to Westchester County. When I arrived at the high-end Italian restaurant, she was already seated, and I could see her face light up when I walked over. Weeks later she would compliment me, recounting, “I looked you up and down, and couldn’t find a single thing wrong with you.” That was Jenny. She stood up and we hugged, and gave a peck on the cheek. She was a couple of years older and inches taller than me, with long blond hair, NYC fashionably dressed, and full- figured—also a first for me, and it drove me kind of nuts!