The Matchmaker: An Overshare

Via TJBNYC76 @ Flickr.

I was in the mood for love.  A year after the breakup from hell, with a few obliging rebound men in the rearview mirror, I decided I needed a new boyfriend.  And I wasn’t the type who liked to sit around and wait for them to come to me.

I launched myself back into the dating world.  To my surprise, there seemed to be plenty of Mr. Right Nows floating around—more, in fact, than before my brief flirtation with binding commitment.  I met men on the internets, at the gym, at friends’ birthday parties, at fix-ups arranged by well-intentioned colleagues.  Just about the only thing I hadn’t tried was old-fashioned professional matchmaking, the kind where you pay a fee to an expert who fixes you up.  I had seen matchmakers’ ads in magazines—usually right next to the creepy ones for Russian mail-order brides.  Would you truly want to order up your beloved from a professional?  Really, who does that?   

Then, purely by chance, I actually met one of these professionals.  She doesn’t advertise.  She’s not a household name.  But she’s one of the most successful matchmakers in America.  I’ll call her Dolly Levi, although that’s not her real name.

♥

I met Dolly through a colleague who was working on a dating book with her.   Within a few minutes of meeting me, she asked if I was single.  By the end of the conversation, she’d put the moves on me.  Her sales pitch was oddly seductive, and it came with props, a small pink “scouting card” that she gave to “ladies with potential.”  The brochure made it clear that this matchmaker was no elderly yenta from “Fiddler on the Roof.”  She was the queen of New York matchmaking, although with an accent—and hair—that were a little more Great Neck than Park Avenue. The brochure listed all the television shows she’d appeared on, from “Today” to “Dateline” plus the papers who’d written about her, including the New York Times.  The brochure also claimed–believably–that she’d been in the business more than 10 years and made over 700 successful matches.  The numbers alone were impressive, and Dolly Levi was no slouch at the hard sell.

“Call my office and set up an interview. We’ll see if we can fix you up with the perfect guy.” 

Hmm…I stuffed the card into my purse.  Curiosity gnawed at me all day, so when I got home I went on-line to learn more about her business (this was before Bravo’s odious “Millionaire Matchmaker” series debuted, or I might have already known the basics).

Here’s how it works: Dolly ‘s clients are all men, and they are all men of means, because Dolly’s services don’t come cheap.  It was never clear to me exactly how much they pay her, but I knew it cost thousands for the full package.  According to her pitch, her clients were men with a lot of money but not a lot of time.  They were lawyers, bankers, CEOs and other masters of the universe. They put in long hours at their jobs, travel often and don’t have time for the parties, the bars and all the dozens of other ways that you meet someone in the big city.   That’s where Dolly came in.   For the fee, she would arrange dates for them and act as a go-between, gently prodding both parties for information after the date to see if it was a success or not.  In essence, Dolly Levi was a headhunter of love.  It was her job to find the “smart, sexy, successful women” her clients wanted.  Like a good casting director, she was always on the lookout for talent, at Barney’s, at Barnes & Noble, at university alumni events and charity fundraisers.  She’d do a quick left-hand check and if she didn’t spot a wedding ring, she’d strike up a conversation, and hand over the scouting card.  The card was your golden ticket into Dolly’s selective wonderland of eligible bachelors.  

But, ticket in hand, I wasn’t entirely sold.  Were these guys such total drips that they had to pay to meet women?   Any whiff of golddigging or sugar daddies usually sends me screaming for the exits and this setup seemed a little too transactional for me.  Over coffee, I consulted my girlfriends.  Even the most skeptical hardened feminists were eager for me to play matchmaking lab rat.  Jennifer, the most recently married, egged me on: “I need a vicarious adventure.  And you never know how you’ll meet Mr. Right.”  

That part is true.  I’d been in plenty of relationships and even when they failed, they never failed because of how we met.  

“But if I do wind up with my dream man, what will we tell people?” 

Jennifer just shrugged. “If it matters to you, make something up. My parents still think I met Tom at Starbucks.”  She’d actually met him in an AOL chat room.

I gave the scouting card another look.  The numbers–if they were true–were hard to argue with.  Jennifer pulled it from my hand and read aloud: “Over 90% of our clients find a lasting relationship within three dates.”   She flicked it back at me and folded her arms.  

“You can do three dates.  You had more than three dates last month.  This’ll be a cinch.” 

I thought it over.  It felt weird, no doubt.   But curiosity was killing the cat.  I’m a sucker for a good New York anthropological experiment.  Plus, I always subscribed to the “you never know” theory of dating.  What did I have to lose?

I called Dolly Levi’s office and began the three steps to those three dates.

Step One: A twenty-minute phone interview.   

As I ate my morning bagel, Dolly’s perky young assistant grilled me on my vital stats: height, weight, age, hair and eye color, where I went to school, what I did for a living, where I lived.  I could hear her tapping away at a keyboard as we talked.  I asked her if she was writing all this down. “Oh, absolutely.  There are hundreds of women’s profiles in here.  We have a program set up so that we can cross-reference them.”  This is not your grandma’s matchmaking.  

Step Two: The interview with Dolly Levi herself.  

Note to single women contemplating professional matchmaking: If you want to hear that you’re smart and gorgeous and any man would be lucky to have you, call your mom. Or your girlfriends.  Just not Dolly Levi.

Step two in the process was not a love fest, or even really an interview.  It was a single-girl cattle call.

Dolly’s “office” turned out to be a café on the Upper East Side.  On certain days of the week she and her assistant took over a corner of the restaurant and women filed in and out all afternoon.  When I arrived, there was a young woman chatting with Dolly, one sitting in a booth nervously sipping a martini–it was 2:30 in the afternoon–and another perched at the bar, looking like she might bolt for the door at any minute.  It occurred to me that Dolly might have deliberately set things up this way to sharpen our competitive instincts. We were all in our thirties and we were all here for the interview.  The room was mirrored, so we could discreetly check each other out.  A wave of cattiness swept over me.  The one with the martini was way too skinny.  The one talking to Dolly wore way too much makeup.  Ugh.  What was wrong with me?

I tried my best to look relaxed but I could feel a knot forming in the pit of my stomach.  What had started out as a lark was starting to feel claustrophobic and pathetic. Was I such a loser that I needed a professional to set me up with strangers?  Was this admitting defeat?   Or was this exactly how I was supposed to feel?  Was this whole vaguely toxic scenario stage-managed as part of the hard sell?

My mood was going south fast, and I was contemplating an escape route–possibly through the kitchen–when the assistant called my name.  I put on my best interview face.

The perky assistant, who looked like she was all of 19, handed my file to Dolly then turned back to me.

“Can I have your driver’s license, please?  Just so we can make sure that we have your name spelled correctly.”

I pulled out my wallet and handed her my ID.  I was fairly sure the information she wanted was not my name–which I’d spelled for her twice over the phone–but my birth date.  

Once I’d been carded, I sat down at the table with Dolly Levi.

“So, Becky,” she smiled as she glanced over my file, “You grew up in Virginia?”

We talked for a few minutes about where I went to school, what I did for a living, etc.  I told her that I had thought about marriage, but never gone through with it.  I knew I wanted have children, and that I would keep working once I had them.  I loved my job but I wanted a family as well.  Dolly nodded approvingly.  

“Nearly all the women I set up with my clients are successful professionals.  My clients are smart men who are serious about smart women.”

Well, that was encouraging. But as the interview continued, it became clear that I probably wasn’t meant to lead with my smarts. 

“What do you do for exercise?”  

If “I want to make sure I spelled your name correctly” was matchmaking code for “I want to be sure you’re not an old hag,”  I was fairly sure that “what do you do for exercise?” was code for “I want to be sure you’re not a fat cow.”  

It should have been obvious by looking at me that I didn’t have a weight problem, but I told her the truth anyway: I ran twelve miles a week.  I did karate, somewhat obsessively.   She looked impressed and made a few notes on my file. 

“You look great.  All that exercise gives you a glow.”

I smiled back.  Who doesn’t love a compliment?  Then she frowned.

“The file says you’re Jewish.”

“Yes, that’s right.”

“You don’t look Jewish.”  Dolly turned to her assistant, “Do you think she looks Jewish?”  

The assistant’s eyes widened and she shook her head.

I couldn’t help but bristle a little.  “Why on earth would I lie about that?” 

Dolly Levi shrugged.  “We don’t see many Jewish girls with fair skin and blue eyes.  It’s important to be sure, because I only fix people up within their own groups.”  

Oh, ick.  That was almost the dealbreaker for me, but I wasn’t going to give her the satisfaction of rejecting me over our contradictory views on mixed marriages.  I fixed her with a cold eye and said, “I’m from a family of Russian Jews.  A lot of us have blue eyes.  Besides, you know my name.  Does it sound WASPy to you?”  (For the record, I have an unmistakeably Jewy first and last name.)

She took the hint and moved on to the next round: where did I like to shop?  Where did I get my hair and nails done?  She frowned again when I told her that I did my own nails, since manicured talons are not karate-friendly, and that I bought a lot of my clothes on-line.  Apparently I was an epic JAP fail.  We did another little stare-down over that.

“Well,” Dolly Levi seemed to relent a little, and leaned forward, “I’m having a party next week for singles, and I’d like you to come.  There’s a client of mine who I think you’ll love.   I’ll send you an e-mail with the details.”

I was in.

Step Three:  The Dating

The first of my dates with Dolly Levi’s clients was in a controlled environment: a singles mixer at a downtown restaurant.  For a mere $75, I got entry, a couple drinks and some happy-hour snacks.  There I would be mingling with some of Dolly’s bachelors, including, presumably, the one she had in mind based on what she’d learned during our interview.

For me, walking into a crowded party where I know absolutely no one is agony.  But I had paid my $75 and I was determined to give it a try.   My girlfriends had promised emergency infusions of Gray Goose if the evening was a total disaster.

I made my way to the bar for my first drink.  With it safely in my hand, I turned to face the rest of the room.  The lighting was low, the piped-in jazz was smooth.  The place was full of men in suits and women in their best “day to evening” professional wear. But it also had the slightly cagey feel of a junior high dance–boys on one side of the room, girls on the other.  The men roamed around the edge of the room while the women were clustered closer to the bar, chatting among themselves and trying to look available.  I caught the eye of the woman standing next to me.

“I didn’t expect it to be this nerve-wracking,” she murmured with a half-smile. She was wearing a leopard-print wrap dress that was long enough to be tasteful but cut low enough to be sexy.

“I think everyone’s nerves are a little wracked,” I agreed.  I held out my hand.  “I’m Becky.”

“I’m Debbie.”  She laughed, “Want to be my wing woman?”

Debbie was a lawyer for a record label.  She was divorced and her biological clock was ticking.  “I don’t particularly care how I find the man of my dreams, just that I find him before I become an old cat lady.”   I liked her immediately.

We made our way to the banquettes at the edge of the room.  Most of the men looked a good ten years older than me.  The low lighting reflected off a lot of bald heads, and many were squinting at their Blackberries.  Still, I wasn’t in this to meet a Calvin Klein underwear model.  After a while, the Blackberries were put away and the men started circling.  Maybe all they needed was a few Scotches for courage.  I couldn’t blame them.  

  “Becky,”  Dolly Levi pushed her way through the crowd and gave me a friendly handshake.  A tall man in a blue suit hovered nervously at her elbow.  “Have you met David?”

David and I shook hands and eyed each other.  He was a few inches taller than me, wearing a blue suit with a blue and gold tie.  Slightly curly brown hair, brown eyes, brown shoes.  Your basic nice professional guy.  We shook hands and I moved over so that he could sit next to me.  We talked a little about what he did–venture capital–and where I lived: Brooklyn.  He confessed that he’d never actually been to Brooklyn.  In fact, he worked so hard he didn’t have time to explore the city.  Or meet women.   He wanted to have a family, but just didn’t have time to look for Ms. Right.  

“So that’s where Dolly comes in.” He admitted with a sheepish smile.  “She’s great.”

Yes, she was great.  She was downright perfect for a guy who wanted to outsource his personal life.  I wondered how on earth David planned to find time for a relationship, let alone a wife and children.   

We talked for a few minutes more.  Debbie seemed to be making progress with a good-looking blonde guy, so they moved over to another table and left the banquette to David and me.

“Is she a friend of yours?” he asked.

“I just met her tonight, but she’s a lot of fun.”  In fact, Debbie was by far the most fun person I’d talked to all evening.  I secretly wished that she and I could just order dinner and hide in a corner.

“She’s hot,” his gaze lingered on the leopard print, “But that dress makes her ass look fat.”

There was apparently another reason David was still single–and it had nothing to do with his killer work schedule.

“Want another drink?” 

I did a few quick calculations–mostly involving the distance between David and the door.   

“I’m good, but you go ahead.”  As soon as he started pushing through the crowd towards the bar, I scrambled to the nearest exit.   I had been at the party long enough to know that it was boring, and that the man Dolly Levi picked out for me was a boor.  $75 seemed a lot to pay for an experience I could have gotten for free at any Manhattan bar on a weeknight.

♥

Dolly called me the next day.  I was sure I’d be in trouble for bailing, and I had an entire “I’m sorry, but this matchmaking thing’s not for me” story all cued up, but all she said was “David said you were nice, but not really his type.”  She was willing to call it bygones and bring on a second eligible bachelor.

“His name is Jake.  He’s brilliant–went to Harvard and owns his own company.  He’s 42–never been married.  I’ll have him call you.”

I had apparently progressed to flying solo; Dolly would now send me out on my own for the date.  The only rule was that I had to call her within 24 hours to let her know how the date went.  This was the best part about the matchmaking experience–no more wondering about why they never called or having to admit you didn’t like them.  Dolly would take care of it—no unpleasant confrontations necessary.

I met Jake for dinner at a restaurant in Brooklyn.  He was slight and boyish-looking with dark eyes and short, straight dark hair.  He looked like a slightly older Matthew Broderick.  He brought me a little box of chocolate truffles, bless his heart, and pulled my chair out for me.  His manners would have made his mama proud, and he had great taste in restaurants.  Unlike David, Jake knew and loved Brooklyn, and we chatted a while about our favorite restaurants.  But when we were looking over the menus, Jake told me three times what a picky eater he was.  No meat.  No shellfish.  No pasta.  He liked oranges, but didn’t actually like orange if it was in anything, like a sauce or a sorbet.  And when I ordered a watermelon salad, he visibly shuddered: “Too watery.”

Jake was also serious about being Jewish.  I was beginning to see why my Jewishness mattered to Dolly Levi; it certainly mattered to her client.  Most of the dinner course was devoted to a rant about Iran and Israel that actually had diners at other tables turning to stare at us.  When I suggested that perhaps not everyone in the Arab world was a terrorist, Jake squinted at me suspiciously, but was polite enough to change the topic—to whether his halibut was fully cooked or not.  

I ordered dessert and began to draft what I’d say to Dolly the next day.  

When the moment of truth arrived, I tried the polite approach, “He’s a very nice guy. I just didn’t feel the connection.”  But it was clear that not only did Dolly want the unvarnished truth, she wouldn’t let up until she got it. 

“If he did something wrong or said something that upset you, I need to be able to tell him so he doesn’t do it again.  These guys pay for my advice.”   She was all business, and I respected that.  I told her about the picky eating, the political ranting, and how he seemed, well, just a little too high-strung for me.

“Look, Becky.  I always say tell people that the second date is 100% better than the first.  Why don’t you go out with Jake again?”

I waffled for a minute.  If Jake and I had been set up by a friend or a family member, I might go out with him again just to seem like I’d given him a fair shot, and to keep everyone happy.  But this wasn’t about keeping people happy.  This was professional matchmaking, and the business dynamic had never been more obvious to me.  It was in Dolly’s best interest to get me to go on a second date; Jake had paid her for the introduction, so she wanted him to feel he was getting maximum face-time for his money.   But there was no incentive for me to go on another tortured date with a guy I knew I wasn’t interested in, unless it was just to keep Dolly happy so she’d set me up with someone else.   That seemed unfair to Jake, though.  He was paying Dolly to find him a potential wife.   It would be unethical to lead him on if I wasn’t interested.  I told Dolly I didn’t think a second date would make any difference—there simply wasn’t any chemistry.  She sounded disappointed, but was gracious about it.  I got off the phone as soon as I could.

♥

I’d had two dates with Dolly Levi’s clients.  If, as she claimed, nearly all the people she fixed up found a lasting relationship in three dates, I was either about to strike out or about to be swept off my feet.  But frankly, I was done.  I wanted out.  

It wasn’t that Dolly Levi’s eligible bachelors were awful; they’d been no better or worse than men I’d met the usual ways.  But the whole scenario felt too contrived, too forced.  Dolly Levi’s approach was cut-and-dried and goal-oriented, which totally worked for me in my professional life but which turned out to be an epic fail when it came to romance, at least for me.  Instead of diving into the messy dating world the way most of us do, Dolly Levi’s clients wanted her to keep dating as tidy and scheduled as their work lives.  There wasn’t any spontaneity to the process.  I missed the thrill of meeting someone randomly, flirting, and walking away with a phone number and an optimistic high.

There was also an unpleasant whiff of desperation about the whole thing, and this time the hurry-hurry wasn’t coming from the women.  In a petty way, it made me happy to know that despite the clichés, it’s not just women whose clocks are ticking.  These men wanted to get married–pronto.  They had serious expectations, and they were paying a premium to have those expectations fulfilled.  Having a man’s need to get married and start a family hanging over my head made me realize how much I enjoyed the initial, casual phase of dating—that early rush of excitement and curiosity that comes with meeting someone new. 

Even if it didn’t work for me, though, there were obviously women who liked this methodical, if high-pressure, approach to romance.  Dolly wouldn’t have been so successful otherwise.  I could see why it might appeal to some women: if you’re shy, or willing to be very objective and businesslike in your approach to dating, it’s reassuring—and easier—to have someone else do all the legwork.  If you can get over the initially icky feeling of being weighed and measured by Dolly Levi and her assistants, you get your date delivered right to your door, and complete with a full P.R. campaign.  Dolly will even act as your safety net if things don’t go well.  But for me, professional matchmaking felt a bit like when my mother used to cut my meat for me at the dinner table: I got cranky because I would rather just do it myself.

♥

I broke the news to my girlfriends: no more dates from Dolly.  I wanted to hang out in restaurants, meet my friends’ friends and cruise other joggers on my evening run. I had given it a month, but the grand experiment was over.  I never told Dolly Levi outright, but she also never called to offer up bachelor number three.  I suspect that with her many years’ experience, she had figured me out too.

Postscript:  This happened two years ago, when the market was robust and Wall Streeters had money to spend on professional matchmakers.  According to the New York Observer, the times, they are a-changing for Dolly.