My Failed Attempt to Become a Lesbian

It was inevitable that at some point, I would attempt to dive a muff. It happened when I was 25. After a series of romantic flops, I was frustrated with boys so I decided to switch over to ladies. Because that's how sexuality works: you choose one when another becomes slightly inconvenient.

There wasn't a particular event that sparked the change, it was more a collection of tiny disappointments: one perfect guy who never called, the night I found a stack of issues of Juggs in the bathroom of a banker I was dating, and the seemingly lovely guy who, after a blissful month of dating, asked if I would grow out all of my body hair. My love life was lackluster, no matter how many Cosmo foreplay tips I had memorized.

On top of my recent man woes, I had just come back from visiting my gay friend, June, and her posse of power lesbians in the south end of Boston. They all seemed hot, soft and oversexed. Their life was like The L Word before the characters started murdering each other. I wanted in. Shortly after my trip, June and her girlfriend Abby (both extremely supportive of my bi-curiosity) invited me to return to Boston for a threesome. I declined. It was a selfless offer, it's not like they were drawn to my raw sexual energy and had to have me. Me and sex appeal got into a fight freshman year of college and hadn't spoken in years. Me and grace hadn't even met yet.

I was tempted to say yes, but they were my friends. I didn't want to see their muffs and I certainly didn't want them to see my panic attack when I saw theirs. I'd somehow end up at the hospital. It'd be a mess. Before all this, I had one previous brush with lesbianism. The summer before eleventh grade, three girlfriends and I drank a bottle of Crown Royal and made out. Little known fact: for private school kids in Los Angeles, having an orgy is as important as joining a sports team or being Bat Mitzvah'd. And there's nothing more fun than being at a wedding and telling the groom that at one point in the '90s, you finger-banged his wife.

Further, though, from a logistical standpoint, how would I have gotten to Boston? Normally I would've flown, but you can't book a flight to an orgy, it's too desperate. On the other hand, taking the bus to an orgy seemed filthy. If the orgy had happened, it would have fast become one of their best stories.

"Hey remember the night we had a threesome with your weird friend?"

"Of course. That was the worst sexual experience I have ever had."

After opting out of the Boston experiment, I was left on my own to find some muff in New York. Luckily I had a Plan B: I'd go to gay bars with Dana, a random lesbian Jewess I knew from camp. It was an odd move since I was barely in touch with Dana, but no more odd than the fact that I wasn't gay.

That Sunday night, Dana took me to a singles party at Bar On A, a dive bar near my apartment. The bar was packed and the moment I walked in I completely froze up. I had always seen myself as a girls' girl - I was comfortable around women but intimidated by men I had crushes on. It wasn't until I walked into the bar that I realized that it wasn't really a gender thing. I'm just awkward around anyone I'm trying to have sex with.

I stood in the middle of the room, mute, for over an hour. Three Amstel Lights failed me and with each quiet nod, I knew I was destroying any chance of hanging out with Dana again. (It turns out that an hour is exactly fifty minutes longer than the longest amount of time you can stand at a party without speaking.)

I fled the scene. But steadfast in my mission to make out with a lady, I consulted my Time Out New York and found a comedy show at the same bar three days later. My plan: I'd go to the show under the guise of being a comedian, when really I was there to fall in love with a woman.

The night of the show, I plopped myself at the bar and looked around for my new love. In 25 years of heterosexuality I hadn't been able to land a long-term relationship with a man, but in one week I was confident I could get into one with a woman.

Within minutes, I found my target: a cute, brunette, Zooey Deschanel-ish hipster in an outfit I would've loved to borrow sometime. She looked over at me. I took that as a sign of mutual attraction but it was probably because I was drunk and giving her accidental fuck me eyes (a habit I've never been able to kick). I knew I'd be nervous, so I scribbled my number on a piece of paper, then strutted over to her and said, "Hey, I think you're cute. Here's my number."

Her eyes lit up and she said "Thank you." This would've been the ideal time for me to start a conversation or maybe ask for her name, but instead I pivoted and walked away. My window of ballsy-ness was closing fast and all I could manage to do next was to run home, turn up the Sleater-Kinney and shriek into a pillow.

Zooey never called, but I analyzed the incident in therapy a few days later (probably a wise time in my life to be seeking professional help). My therapist was gay so I was pretty jazzed to tell her I gave my number to a woman. Above seeking psychological help, my #1 goal in sessions was to get her to like me. My secret dream was for her to stand up after I made one of my insightful quips and shout "I DON'T CARE IF IT'S AGAINST THE RULES, YOU AND ME NEED TO BE FRIENDS FOR LIFE!"

I recounted the story as charmingly as I could. "Wait, what bar were you at?" she asked.

"Bar On A."

"What night was it?"

"Wednesday."

"Ali, Bar On A has a gay night. It's on Sunday. If you were there on a Wednesday, I'm pretty sure you gave your number to a straight girl."

At that moment, my therapist did not stand up and express the need to break her therapeutic oath and befriend me (her loss, we could've had fun). But it's always good to be in therapy when you have that kind of revelation so you can deal with it immediately.

That afternoon I returned to my life as a heterosexual, and two weeks later I met a man and fell in love for real.

Ali Waller is an LA-based writer and stand-up comedian. She's written for "Late Night with Jimmy Fallon," "Chelsea Lately," and "American Dad," and has developed original comedies for HBO and MTV. She was recently listed as a "Comedian to Watch" in Time Out NY, and co-wrote a screenplay that made the 2011 Blacklist. She has a crippling addiction to Twitter.

[Image by Jim Cooke, source image via soosh/Shutterstock]