A Hundred First Dates

Most straight single women I know have sworn off Internet dating altogether, after meeting men who are married, otherwise dissembling, or only interested in sex. So I was surprised when my 41-year-old lesbian friend, Alexandra, told me that after going on about a hundred dates with women she met on Nerve and PlanetOut, she finally met her girlfriend, Jill. After a year together, they have just bought a loft in Tribeca and are considering adopting a child. Incredulous that she had managed to stay optimistic after so many failed dates, I asked Alexandra to explain her strategy.

A media executive who is athletic and peppy with clear blue eyes, she went online with a positive attitude and a belief that she was going to find the right person. “I have a friend in L.A. who dated a bunch of jerks and then decided she wanted to meet a nice guy and marry him,” she says. “She changed her dating strategy, and six months later, she was engaged. I say she ‘chef-ed’ her life, like making a chef’s salad. That’s what I was trying to do.”

Alexandra chose the Internet because she was tired of all the different lesbian scenes and felt she’d have a better chance of meeting someone new online. “What else am I going to do—go to Henrietta Hudson, where the girls are barking at each other, or Starlight, where everyone’s 21 and looks like a recent Sarah Lawrence grad who’s going to lecture you on semiotic theory? I figured that if I looked outside of the different cliques, I would meet a whole new pool of people.”

She wanted to meet someone who didn’t have banal interests, so she screened the ads closely. “In lesbian culture, there are many warning signs, especially when you’re over 35. I did not go out with anyone who listed Patricia Cornwell as a favorite writer, said she liked listening to ‘Melissa,’ or who opened her ad, ‘Hey, ladies!’ And I would never write anyone who listed ‘wine tasting’ as a hobby, because that’s lesbian-speak for ‘I need to go to AA.’ ”

Unlike most straight daters, Alexandra did not include a photo in her ad and didn’t limit herself to answering ads with photos. “In the lesbian world, it’s a little more okay not to put a photo, because we’re more private. Even though lesbians are looks-ist, there’s more of a stigma against seeming looks-ist. If you don’t post a picture, it’s a way of going against heterosexual norms.”

When she found someone she liked, they’d exchange photos. “This one girl looked really sturdy and practical and was posed in her Jeep Cherokee with her arm slung out the window. The whole ambience was too ‘Honk honk—let’s go to the park!’ ” If Alexandra didn’t like the picture, she’d e-mail to say she didn’t feel a connection. Sometimes she got rejected first. “A lot of lesbians have particular types. For example, I can’t date an overtly femme-y girl. Knee-high boots with heels scare me. I prefer Prada.”

On most dates, she was able to glean quickly that it wouldn’t work. “Someone said to me over dinner, ‘I was asked to leave the ashram.’ Another woman said, ‘Now that I’m coaching softball instead of playing … ’ It was a little creepy to be that interested in softball.” Though she never used it, Alexandra kept her friend JoJo’s number for emergencies. “She’s a very voluptuous young Phyllis Diller type with a booming voice. I had her on speed dial so if things got bad, she could come running in and say, ‘Get home, you bitch, and take care of our Chinese children!’ ”

If she didn’t see romantic potential, even if there was physical chemistry, she left. “I think when it’s a girl, it’s easier to extricate yourself. With guys, sex is an expectation. They want to have drinks and fall into bed. With girls, you can say, ‘I have to get up early and go to work,’ and you don’t get an argument.”

When she finally spotted Jill’s ad, she responded immediately: She was interested in design, and sounded down-to- earth. They met at Odeon for a drink and wound up having dinner. Though they both felt chemistry, they didn’t have sex until many dates later. “I didn’t want to rush,” says Alexandra, “because I had a feeling I’d met someone important. I knew there was plenty of time.”

A Hundred First Dates