Single in the City: Matchmaker, Matchmaker
by Esther Zinn
June 3, 2011
My most recent dating adventure involved meeting with a professional matchmaker. Well-respected and renowned for her matching prowess, I figured it was time to pull out all the stops and get down to business on fixing my love life– to become proactive about   working on my flaws to find the right girl.

And thus, I called in an elite matchmaker at the very top of her game.

I sat across from her at a table, while she eyed me with a shrewd and analytical gaze, acquired from years of sizing up people fearful of dying alone.

“So. What do you think you need help with in your love life?” she asked.

“Well…I feel like the type of woman I’m trying to find is over here,” I said, pointing to one end of the table. “But what I’m getting is over here.”

“Oh. So you’re a lesbian.”

“Well, yeah.”

“Got it. Well, from what I can see here, you’re a butch. Am I right?”

I was wearing a pink shirt with ruffles.


“Okay listen honey. If you want to nab a New York lesbian, you’ve got to get more fashion forward and go shopping for better clothes. Because right now, you’re looking butch to me!”

“But I’m often chastised for drinking cosmopolitans by my friends! Who say I’m too femme!” I protested.

“Well, they’re wrong,” she countered. “And you need to step it up! Not only do you not look femme, but you kind of look like a man at this point.”

I realized she was right…coming from San Francisco, possibly the least fashionable city on the face of the planet, I indeed looked like I fell off of a turnip truck when I moved to New York a little over a year ago, and never quite ended up looking as polished as girls from the Empire state.

“So how old are ya? 34?” she asked.

“I’m 29,” I said.

“Definitely thought you were in your mid-thirties.”

There was a long, pregnant pause after that one. But better a pregnant pause than menopause, which is apparently the milestone phase of the average woman’s life that I appeared to be entering in.

“You have to pull yourself together!” she asserted. “Better clothes! Lose the weight! We’ve got to get you in a dress to make you look nice and show off those curves! Have you thought about wearing some hair extensions? There’s a lot of work to do here, we’ve got to get you looking like Kim Kardashian or Jennifer Lopez!”

“Oh my,” I thought to myself. “There is no way that’s ever happening. And by ‘that’ I mean looking like J-Lo OR getting the hair extensions.” I’ve always thought of hair extensions as basically femme toupees.

And then I thought of Meatloaf. “I would do anything for love. But I won’t do THAT.”

Another long pause settled over us. Nervous tension, perhaps concerning the extensions. Because I looked down at the floor and envisioned a freaking carpet draped over my head, passing as a soft, luxurious mane.

“So. When it comes to women, do you like to approach first, or you do prefer them to approach first? You like to be the leader, or the follower?”

“I get r-really sh-shy,” I stammered. “I’m too scared to make the first move, too afraid of rejection!”

“Oh, so you’re a bottom,” she concluded.

“I am NOT a bottom!” I shouted. “I’m more of a swi–”

“Well, all i’m hearing out of your mouth is ‘Blah blah blah, I’m Esther the bottom.’ ”

“I’m not a bottom!”

“Well, then stop sending mixed signals. So…what kind of woman are you looking for? What’s your type?”

It has always been sort of difficult to explain my type, which is pretty much right down the middle. I tend to go for femmey tomboys. Do you remember being a kid, when your parents would take you to the frozen yogurt shop, and instead of wanting to choose one flavor, you were like, “I’ll just have the swirl, thanks.” Well that’s kind of how I feel about femmey tomboys. They’ve totally been my flavor of the month…for 11 years now.

“I like femmey girls. Who are also kind of tomboys. I guess femmey tomboys,” I said, which I’m sure didn’t help at all.

“Okay. What’s the number one most important quality you would identify in a woman?”

I tapped my lip thoughtfully and looked out the window, thinking about the quality that I find most important in a potential mate. Would it be humor? Intelligence? Passion? I thought about the one distinct quality that all of my long-term, U-Haul girlfriends and memorable relationships all shared, the one I have discussed many a time in this very column.

“All I want is a woman from New Jersey.”

“You WHAT?” she cried. She threw up her hands, looking utterly baffled.

“Yes. That is exactly what I want.”

“What are we talking here? Like the girls on Jersey Shore? Jerseylicious?”


She took in a breath, and a moment to think about my standards.

“Well…okay. I know your type exactly. We need to target a woman who has enough money to afford a hotel room. For when she comes into the city on the weekends.”

“I really want to find a Jersey Girl who makes that much money,” I said, filled with hope.

“Well, that’s obtainable. Where are you looking?”

“Bars. Online. General dating sites.”

“I don’t like that one bit!” she retorted. “You’ve got to find a personal ad site for lesbians.”

“There aren’t a lot that are really popular. Not specifically for lesbians, anyway. And whenever I make a profile on a site for everyone, I’m only contacted by straight ladies and men.”

“You’re just making excuses now!” she thundered. “All you’re doing is whining, whining, whining. Come back to me when you’re done with all of that whining.”

Another long pause settled over us. I thought to myself that maybe I was whining, and generalizing. That it was time to stop making excuses.

She broke the pause.

“Do you have to pee? Because I have to pee. Come on, I’ll take you to the bathroom.”

I thought to myself, “Oh my God, I am peeing next to the matchmaker. Its come to this.”

I left the session with a strong resolve to get back to the gym, do a complete life and body makeover and really do the hard work towards fixing my love life. In particular, really zeroing in on what it is that I want and being less afraid to make the first move. And as luck would have it, by following her advice, I asked out a cutie and scored a date just a few days afterwards! Unfortunately, this one has broken the streak and is not from the Garden State, but I suppose I must be realistic and can’t have it all.

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