I Was a J-Date Pseudo-Lesbian

I am a New York City–dwelling, L Word–watching, liberal-minded hipsterish hetero. A girl who has always thought it would be kinda sorta maybe cool to make out with another girl but never has. That kind. And yet….

As my 30th birthday approached, I found myself single — and celibate — for a longer stretch than I've ever wanted to be. As more and more friends settled into the adult worlds of marriage and parenthood, I started lamenting my missed opportunities, as if 30 marked some sort of slow decline toward death.

I was embroiled in a tumultuous on-again, off-again relationship — with JDate. What had once been exciting — a sea of eligible Jewish men for the taking! — had become a virtual waiting room of guys who liked to work hard and play hard and enjoyed staying in as much as they liked going out.

It was a particularly heinous-feeling I'm-never-going-to-have-sex-again kind of night when I received a Flirt from ArtsyGrrl18*, a curvaceous and pretty woman seeking a woman. Her message was nothing more than a cheesy canned pick-up line chosen from a drop-down menu: "You're burning up my monitor — are you always this hot?" But I felt a flutter in my stomach. And while, yeah, OK, I'm straight, I didn't really care. I was smitten. Sort of.

I was sick of men. Sick of corresponding with guys only to meet them in person and find out we have zero chemistry, to repeatedly come to the soul-crushing realization that the dream lover I'd imagined doesn't exist anywhere in this universe. Sick of pretending to be indifferent just so I won't scare them away. I'm not indifferent. Why should I be? Men could keep their issues and their fear of commitment. They could have their erectile dysfunction and their emotional unavailability. I was moving on to bigger, better (softer, nicer-smelling) things.

I immediately drafted a response. "I'm burning up your monitor?" I asked incredulously. "Come on, that's almost as bad as some of the guys on here." My reply accomplished a few things. It flirted back, it put her in her place and, perhaps most important, it reminded her that I was used to being courted by men. I hit send without stopping to wonder what I was doing.

A few days passed with no reply, and I began to worry. Had it been wrong to mention men? It was no secret that I'm straight. What was the sense of playing down that fact when it was, in fact, a fact? Maybe that was even part of what drew her to me — I was, in theory, off-limits. Every day I skimmed through message upon message from a nondescript crop of men, obsessively refreshing my in-box, automatically declining IM requests from the likes of Mensch4U and JewtasticNYC, hoping that each new page would bring a sign of ArtsyGrrl18.

And then, on the fifth day, there was light, in the form of a blinking-envelope new-message icon. "LOL, Carla," she'd written back. "You rock so hard." How adorable, I thought. What a gem! It's true, a similar response from a man probably would have found its way into my Trash bin. But I was hooked. There was no doubt about it: ArtsyGrrl18 would signify my first trip into Girltown.

"I think I'm going to go out with a girl!" I told friends. They all looked at me strangely, as if I'd told them I was thinking of piercing my nipples or moving to India, that I was going to do something that sounded adventurous and edifying but in reality was probably foolish and regrettable. And they all asked the same thing: "Do you really want to date a woman?"

A good question. Did I want to date a woman? Well let's see. I love women. Most of my closest friends are women. But no, all right, that's not what they meant. So did I want to kiss a woman? Well, sure! Maybe. Life's too short not to try it, right? And kissing's always nice. OK, forget kissing. Did I want to get naked and sweaty and dirty with a woman? Oh boy, now it was getting tricky. Maybe if Susan looked like Diane Lane. (She did not.) And maybe if the prospect of a man were anywhere on the horizon. (Mensch4U's ability to feel as comfortable in a T-shirt as in a tux and JewtasticNYC's exciting life as an actuary weren't exactly getting my blood going.) Maybe if I could keep my eyes closed and spend more time receiving than giving. Whatever, I thought. I'd figure out the particulars later. I was going to do this, damn it, so I decided to address my reservations the best way I knew how: by ignoring them.

Susan and I e-mailed for about a week, and then she decided we should talk on the phone.

When she called, on a lazy Sunday afternoon, I jumped, even though I knew it was her before picking up. She'd scheduled the time for our phone date (who schedules a phone date?), but even if she hadn't, there was an urgency in the ring that told me it was her. Or maybe it just seemed that way.

But the conversation was easy. There were no awkward silences. Aside from the weird feeling in my stomach, talking to Susan was just like talking to a girlfriend. You know, a girl friend. When she let slip, "You're cute," or worse, tried to talk about "us," I shifted the topic to more platonic things.

At one point, I managed to get out, "I don't know how much of a tease I'm being." It was the only thing I'd rehearsed, the one thing I'd known I would have to say, even before the phone rang.

I was still speaking when she said, "That's OK." I could feel the period of my sentence hanging somewhere in the middle of hers. She wasn't listening to me. "Do you like more masculine or feminine women?" she asked.

Oh, Jesus. "I'm not sure what kind of women I like because I've never liked a woman before."

I had thrown in the "before" to be kind, even though I knew lying now might result in an even bigger cruelty later. What was true was that I was curious, I was intrigued, I was flattered, I was bored. But I did not know if I was interested. And wasn't that what she was really asking?

When she pressed it further, I tried to think of celebrities I found hot. Jennifer Lopez, sure. Rosie O'Donnell, not so much. Scarlett Johansson? Yes, please. Lea Delaria? Hell to the no. "Feminine, I guess."

Which led to a discussion of the photographs she had posted with her profile. "The one of you in the red top is nice," I said. I regretted it as soon as the words were out of my mouth. The red top was pretty low-cut. I could hear her smiling.

"You like the boobies, then."

"You just look happy in that picture. And red's a really good color on you. " There was no fucking way I was talking about boobies.

We chatted a bit longer and hung up with a time and a place to meet. Ten minutes later, the phone rang again. "It's me," she said. Her sense of familiarity annoyed me, and the second call caught me more off-guard. Men did not hang up the phone and call back 20 minutes later. At least not men I've ever known. I suddenly understood that old joke: What do lesbians bring on a first date? A U-Haul.

"You make a person want to cancel her appointments and just keep talking to you," she said. I wouldn't have believed it if I'd read it in a book. I'd have chalked it up to melodrama if it were a line in some asinine romantic comedy.

"Oh," was all I could muster.

"Can you talk a bit more?" I was already planning on telling her not really, but then she added, "Just for like 20 minutes." It was so exact, so needy, so faux casual that I couldn't even consider saying yes.

"Look," I said, "I've really got to go. We're going to see each other in a few days." I could sense disappointment on her end, but what could I do? This woman seemed crazy! We'd never even met! Didn't she know you can't just act on every impulse you have? That you need to play the game? I shuddered. What the hell was going on here?

Susan's disappointment didn't last long because that night, around midnight, my phone rang again and we had our third conversation of the day. On the first day we'd ever talked at all. I had gotten my wish: an attentive mate who said what she meant and meant what she said. And I couldn't have been more freaked out about it.

But the truth is I enjoyed talking to her. In fact, I opened up to Susan in that third conversation more than I have with some men I've dated for months. But Susan was sensitive. She didn't spook at the first mention of imperfection, of baggage. She was, after all, a girl.

The week after our first day of phone calls passed with alarming speed. I grew increasingly panicked as our date neared. "Blow it off," one friend advised. "You're not a lesbian!" A good point. And yet, didn't I owe it to myself to see how this thing played out? I'd already come so far! Wasn't it time to live a little dangerously in homage to all the friends who were now shopping for Bugaboos and obsessing over seating arrangements? Going out with Susan wasn't something I necessarily wanted to do, but something I felt I should, to build character. I mean, going weak in the knees for someone or wanting to tear his clothes off the second you see him is nice, I guess, but it doesn't hold a candle to character, right? Right?!

Sunday arrived, and I woke up groggy. My sleep had been fitful and uneasy. I was supposed to get in touch with Susan to confirm the details of our date. I didn't. Later that day I received an e-mail from her: "Am I right in assuming you've lost interest in meeting me?"

(Even worse, she had accidentally sent a slightly altered draft of the message, too. I was mortified for her. I was mortified for me—how many times had I agonized over every syllable in a one-line missive to a man who probably skimmed it anyway, too distracted by ball-scratching or mirror-gazing to care?)

My response to Susan's e-mail surprised even me: "What makes you think I've lost interest?" Holy shit, I thought. I am a guy. I am a motherfucking guy. I was full-on playing with her head, and it terrified me how naturally it came, how easily and effortlessly the transition had occurred. Didn't I complain that men can never just make a plan and stick with it? That they're purposefully evasive? That they toy with our emotions for sport? What could I have been thinking?

Not much, I guess, because I strung Susan along for a week or two. I answered her phone messages with e-mails. I canceled plans at the last minute once because I got stuck at work and another time because a friend sprang last-minute birthday plans on me (a last-minute birthday?). Finally I decided to do something no man has ever done with me: I decided to come clean.

"Look," I wrote, "I'm really sorry. I never meant for this to happen or for things to get this far only to have me chicken out. I just don't think my heart is really in it. And I sort of wish it were. I'm truly sorry if I've hurt you."

And she, also being female, responded in a similarly refreshing way: with honesty, compassion and understanding: "I'm a little bummed because I thought we were connecting, but no worries, OK? Please. Call me if you ever change your mind. Goodbye, beautiful."

Her e-mailed crushed me. It made me want to write back and tell her I was wrong, that we should meet, but I didn't. The kindness was what I was attracted to. It always had been. I just couldn't get down with the boobies.

In the end, Girltown turned out to be less like an exciting vacation spot and more like a restaurant I wanted to gawk at through the windows but never actually eat in. Today when friends and I are contemplating how to proceed with men we're dating, what the best course of action is, we invoke the question WWSD — What Would Susan Do? We figure out the answer, then do the opposite. And I hate that we have to. But I guess that's the price you pay for being a straight girl.

*Names and Jdate handles have been changed.