INTRODUCTION

Yesterday I was a divorce attorney.  Today I am a Matchmaker.  Crazy, I know, but that’s my life. 

I went to law school and decided to pursue a career in divorce law basically because my mom suggested it and I thought it could be fun. I didn’t put all that much thought into it. My mom said that maybe divorce law would be the most people oriented, and I agreed. 

I practiced divorce law for awhile, and it was in fact very people oriented, but in an unpleasant way--- you did help people, but at a time when they were at the lowest point in their lives, and depressed all the time which in turn made you depressed all the time. I soon discovered that most divorce attorneys burn out quickly. 

To counterbalance the potential burnout, I began throwing parties. I took over these swanky clubs early in the evening before their regular patrons showed up. I gave the management a small cut of the door, I charged $20  collected by one of my “bouncers”, (my brother Sean or my brother Christopher) and I would have several “playmates”, (younger sisters of my  brothers’ friends) standing, scantily-clad by the door and collecting business cards so I could invite the attendees to the next shindig. Each evening would end with me laying on my bed surrounded by hundreds of twenty dollar bills and hundreds of business cards of all of my new friends.

 I loved throwing the parties, I loved meeting the new people and I found that I was really good at remembering little factoids about people and exceptionally good at introducing couples.  Sometimes I couldn’t help myself, I would see a guy on one side of the room and a girl on the other and I would grab them by their hair and pull them towards each other, make the introduction and walk away. Time and time again, I heard through the grapevine that these couples were dating, had gotten engaged or had even gotten married.  Soon, according to the Jewish faith, I had already earned a place in heaven, since more than three couples had ended up getting married through my introductions.   

For years, I continued to start up all sorts of singles businesses-  organizing group share vacation homes, organizing co-ed back to summer camp weekends, planning more and more $20 admission singles parties, putting out singles newsletters- all the while subconsciously wanting to be a Matchmaker, but refusing to officially step up to the plate and declare my Matchmakerhood.  I remember with particular fondness¸ my idea for a co-ed back to summer camp weekend where 300 or so single people would travel up to sleep-away camp in upstate New York to relive their camping days  Originally, the  fantasy was that I would sell out and have to put people on a waiting list, and I remember the reality was that I  dragged myself and my very patient boyfriend of the time up and down the beaches of Southampton, approaching strangers and trying to convince them to purchase tickets so I wouldn’t have to cancel the weekend.  Though a near disaster with no profit whatsoever,  the weekend wound up being a lot of fun and I walked away with a few thousand new friends whom I had met combing the beaches of the Hamptons. 

I also recall with fondness the newsletter I decided to mail out to all my new friends which I called In the Loop. I pontificated about being single in New York, suggested great places to go as a single person and wrote a Dear Samantha column where I would answer people who wrote in their serious dating dilemmas (I made up more than a few for the purpose of the first column).  I promised that the newsletter would come out monthly, it never came out again and in retrospect I am not sure that all that many people missed it. 

In the beginning, some of my singles ventures were hare-brained, to say the least, but in the interim I built up a pretty kick ass mailing list of the best and the brightest young singles in the New York tri-state area.  I probably could have handled being a divorce lawyer for a few more years but what was the point?  I always wanted to have my own business, to be something, someone a little different, even unique. And I definitely had a following in the singles world, so, I decided to become the world’s youngest Matchmaker.

Becoming a full fledged Matchmaker didn’t just happen for me overnight. It took me quite some time to get comfortable with the notion that people were going to be thinking of me as a Yenta. In my mind’s eye, a Yenta was that ugly loud woman in Fiddler on the Roof, complete with a hair growing out of her chin, or one of these real life Matchmakers, let’s call them the Maries. There were a bunch of Maries, based in New York, who had cornered the matchmaking market. The Maries were the kind of matchmakers I so didn’t want to be. They just had this way about them that I hated, they were pushy, and aggressive and would never take no for an answer.   I never really understood why anyone would ever trust any of them with their personal life, but I guess when there is only one game in town, beggars can’t be choosers.  The thought of my being equated a Fiddler matchmaker or one of these real life Maries was a little more than I could handle for a really long time. 

Meanwhile, several of the Maries got wind of me.  One called me trying to convince me to hire her to find my husband.  That was just plain comical because at the time, I was 26, had dates up the wazoo, and the last thing I was looking for was a husband.  Another Marie found me some time later, and  invited me to a singles party she was having, and she suggested that I come and pay $150  so I could check out her roster of eligibles.  I told her I would think about it and that seemed to satisfy her enough to let me off the phone.  I immediately called my mom to laugh about the phone call but my mom became serious and said I should go to the party, and do some research. 

I guess my Mother knew I was destined for this business.  You see, when I was in law school, a friend of mine moved to Houston and upon arriving she went to the synagogue there and signed up for a dating service which cost $100 as an initiation fee and then $2 an introduction; she met her boyfriend who ultimately became her husband that way. Because of her story, I developed a preoccupation with starting a dating service, of course I wanted to charge a little more than $2 a date but I liked the overall concept of it nonetheless and I wanted to incorporate something else into the idea that the dates only be over drinks.  So I came home one day and told my mom that I wasn’t going to be a lawyer, I was going to be a businesswoman and I was going to open a dating service.  My mother laughed and said that I was in law school and naturally I would be a lawyer.  Of course that’s what a Jewish parent would say!  At any rate, a few months after my mother instructed me that I would be a lawyer, she saw an advertisement for a dating service that introduced people over drinks and over lunch.  She cut out the article, handed it to me and said with a smile that maybe I was onto something, but that something should be after law school was over. The article fueled my interest in opening my own version of a matchmaking business, but I was already in law school, I figured I should listen to my mother, this time, and put my entrepreneurial aspirations aside for the time being. 

Getting back to my many Maries story, when I called my mom and told her about Marie’s invitation to her party, my mom said that since I had always had this preoccupation with dating services I might as well swing by her event and see what was what.  So, I went to the party, alone, because I didn’t think it was fair to ask one of my friends to fork over $150 for what might be a terrible party.  And terrible party it was—for starters, the youngest man there probably could have been my father, and the people were just tacky and awful. I learned a lot about this Marie and her clients and her tactics.  She apologized profusely about the age discrepancy and swore on a stack of bibles that it wasn’t always like this. Right Marie. 

Time went on and I kept matching people up at all my crazy singles events but I hesitated about opening a real matchmaking service because of my preoccupation with the Maries. I actually spent time in therapy obsessing over the Maries.  My therapist finally convinced me that I could actually offer a completely different service to the singles masses and that I didn’t have to be a Marie at all.  I guess that’s why therapists get paid the big bucks, because finally the light bulb went off in my head and I realized that I would never be a Marie because that just wasn’t me, and that I would succeed by offering New York singles an alternative.          

Soon, I set out to come up with a brand of Matchmaking that would be cool.  I decided right then and there that if I started my service and the only people who called were unattractive and awkward and hadn’t had a date in years, I would go out of business immediately and that would be that.  I had no interest in becoming the Queen of the Undateables in New York.  So, I determined that the only way I would stay in business and make my service work would be to find people who were socially adept and desirable and convince them that they truly wanted and needed my help. Ultimately, I wanted a service that would not just be successful but even fashionable and hip.

First step, allow people to think that mine was not a dating service, even when it was one.  I know, it sounds crazy but it worked.  I decided that I would offer one on one dates, but I would also offer introductions over small group dinners. This way if someone wasn’t comfortable admitting that they joined a dating service, they could gloss over the truth by saying they joined an eating club or a dining club in which a small group of people would get together every so often to eat to in a trendy restaurant.  They could leave out the part that the real objective of the group was to sit with single people looking to meet their mate. Good idea right?  I thought so.  And that’s what I did.  I came up with this corny name, Table for Two (or More) which basically meant that you could sit at a table for two(a date) or a table for more than two (a group dinner).  Then I put together a very classy brochure that explained the idea and I mailed it out to 7000 of my closest friends. The 7000 had been enjoying free introductions over the years simply by attending one of my events, so they knew that I knew a lot of people and this was the key to starting and succeeding in the matchmaking business. So, I hooked up a business phone line and I sat and waited and waited and waited for the phone to ring.    

The phone rang every once in awhile, mostly telemarketers, a few lonely hearts and one call from a Marie saying that she thought it strange that I would mail my brochure to her (I didn’t of course) but she would love to talk to me about my business.  Sure Marie I got some calls coming in right now let me ring you back.  In other words, buzz off, I’m the competition now.

Eventually a few of the “Desperados” seemed a little less undateable than the rest of the callers, so I started meeting with them.  I figured at very least it would be good practice for when the heavy hitters got around to calling--- after all they were very busy people.  First girl I met with was a girl named Jennifer, 29. cute, worked in advertising. Of course, I didn’t tell her that she was my first.  But she was my first, and I asked whatever questions I thought I needed to ask her.  During our meeting when she told me that she was surprised that I didn’t ask her certain things, I immediately added them to my repertoire.  I met with her for two hours,  for free, and she never signed up.  Oh well, her loss.

The next guinea pig was a girl with blond curly hair, an opera singer who  had an unusually high pitched voice.  She wasn’t bad looking but I remember thinking that her voice would probably drive the guys crazy, because it was definitely going to drive me a little nutty.  I wondered if it was worth it to take her money...  But then she offered it, my first $1000 check, and guess what, you got it, her voice became a little less irritating.  So, I continued to putter along, a phone call here, a lonely heart there, and I would alternate between thinking I was the world’s biggest idiot for trying to start my own matchmaking business and optimistically telling myself that the business would take off any day, I just had to be patient.

Then came my big break. About six weeks into my entrepreneurial venture, I met a reporter for a major magazine. She asked what I did and I told her. As a matter of fact I talked her ear off, going on and on and on about how fabulous my business was and how successful I had been, how my phone was ringing off the hook and how I had the most hip people in New York as clients but I was unable to name names due to my confidentiality clause. The fabulous business part was true, the cool client list was maybe a bit of an exaggeration; I kind of left out the part that the clients weren’t all that cool, yet.  Well guess what? She bought it.  A few days later, she called me and she said she wanted to write a story about me and my booming business with a photograph and everything.

 And she did just that. Not only did she write an article, but she wrote a glowing, positively enviable article. She made my business sound unbelievable, sought after by only the most desirable singles in New York, with waiting lists and unpublished business lines. Once the article came out, I realized that now I might just have the opportunity to be the stellar Matchmaker that I knew I could be. I could help a lot of people who needed my help, and they would want it once they knew I existed.

The day that the magazine hit the newsstands I was very nervous.  It was do and die now, if the dateable people called, no, when they called, I needed to be able to put my money where my mouth was, or I would be out of business very quickly.  My anxiety was well founded because I was besieged with fifty seven phone calls before noon!  Every person was calling and requesting to meet with me in person.  The writer of the article became my favorite person on the planet!  The power of the press was truly remarkable! When I woke up that Tuesday morning, I had a whole bunch of clients but some of them were maybe not all that set-uppable  and then by lunch time, I had fifty seven A-list people who wanted to meet with me and pay $1000 for my expertise and services! 

Up until this point I was meeting with everyone for free, but all of a sudden my time was becoming valuable. I panicked and called up my “business advisor,” a guy I had dated who went to Harvard Business School, and I asked him what to do.  Harvard boy told me that when I called back the next five people to schedule appointments, I needed to tell them that there was a $200 consultation fee to meet with me.  And then, I needed to see what happens: the less serious callers would balk and for those that didn’t, I have myself a consultation fee. 

So I did just that, the rest of the afternoon, and guess what, no one batted an eyelash. So much for that plan. By the end of day one, ninety six people had called and I was truly panicking.  It would take me two months to meet with ninety six people.  So I called back Harvard boy and asked for some new advice.  He then said, tomorrow morning tell the first five people I called back, that I had a $400 consultation fee and see what happens.  He said that some people would think that number was way too steep (I don’t know buddy, they were supposed to think that of the $200 fee; I am becoming quite desirable you know.) and then I would have a manageable number of people to meet with for $400 each. So the next morning, I started asking for $400 to meet with me, little old me. And   exactly what Harvard boy predicted, happened, some people said buzz off, and the more committed people said fine. And so the kookiness began….

SEPTEMBER

September is an interesting month for matchmaking. I guess every month is, but September is especially interesting because many peeps come my way.  First of all, summer has ended.  Why is this significant?  Because a lot of single people were expecting to meet the person of their dreams over the summer-when people are tan and look better, healthier, and thinner, women wear sexier clothing, and more bare clothing that attracts the hombres, there are a lot more people out and about, happy and interacting and people take vacations to try to meet people, but they didn’t. Moreover, in my cities (New York and Los Angeles) a lot of people buy shares in vacation houses (in the Hamptons and in Malibu) and these houses are hookup central; there we have tons of single men and women all looking to meet and be met. Unfortunately for a lot of the Desperados, they meet a lot of people, have a lot of flings, but come out of the summer still alone.  That’s where I come in.  They gave it the summer, four months and still nothing, so they come to me, hat in hand.  Yes, I might be sloppy seconds in this situation, but I am okay with that.

Desperado #1

Yours truly, Me

I am definitely Desperado #1.  I should be in a great relationship, but I am not.  I should be married but I am not.  I guess there are no should be’s in dating land, but there are.  I really haven’t wanted to be married until recently, but now, well now, I think I am ready.  My guy of the moment, Jerkoff, my guy of the past three years, on and off, Jerkoff.  The guy of my future, probably not Jerkoff, but I just can’t get him out of my system.  I am such a “Desperado.”

Desperado #2

MR. GAZILLIONAIRE

The hundred million dollar man with seven houses--- my first gazillionaire and a real blue blood WASP to boot.  He sat down at the table and the first thing out of his mouth was “I am worth in excess of a hundred million dollars.”  Period. Then he took a sip of his drink.  I wasn’t quite certain what to say to that. My left eye started twitching a bit because he was my first gazillionaire.  And then he went on to explain that it was important that I know just how wealthy he is so that I make certain to introduce him only to women who would be comfortable with a man so wealthy.  I could probably think of a few.  He described the seven homes he had around the world.  There was the Palm Beach one for winters. There was the Vail one, for all his skiing needs. There was the CT one, a big ass country house. An apartment in Paris, for when he goes shopping. Two apartments in Manhattan, one on Fifth Avenue to impress the ladies and the other on Central Park South, for when he is slumming it.  And one more, in South Hampton so he can go to Southampton Bath and Tennis.  What kind of girls did he ask me for?  Supermodels of course, but waspy ones!

******************************

September 6

I took a table at the Regency hotel and held court all day.  I chose a table in the corner off to the side. I wanted to try to establish it as my table so that the waiters would get used to me being there and would know where to send my peeps. I chose this table because it was private but also because it gave me a full on view to the door so I could see each Desperado as they walked in.  I scheduled three back to back consultations.  Twelve hundred bucks in five hours seemed like a very doable number before the day started but let’s just say after the third “Desperado” of the day, I needed a big break or a big drink.

Desperado #3

WOULD YOU INTRODUCE HER TO BRAD PITT GUY

Brad Pitt guy.   He sat down at the table decked out in stylish New York clothes—Gucci loafers, a blue blazer with gold buttons, a Faccionnable shirt, a Rolex white-gold Daytona watch.  He was medium height, maybe 5’8, and claimed to be very wealthy. He clearly didn’t know about my hundred million dollar man or he wouldn’t have been bragging.  We went through the consultation and when I started describing the women I wanted to introduce him to, after every description he would say, “She sounds good but would you introduce her to Brad Pitt?”  I kept looking at him more and more closely to see if somehow I was missing the resemblance or relationship to Brad Pitt himself.  Finally, I had to say what had been dancing around my head for quite some time--- “Buddy, first of all Brad Pitt is not available right now, he is with Jennifer Aniston, secondly I don’t know Brad Pitt so I have no idea who I would introduce him too and thirdly, hate to break it to you, but you are NOT Brad Pitt!” He said, “Well, there’s no reason why I can’t date like he does.” There isn’t?

Desperado #4

MISS 39

 The “I’m a 39 year old female corporate exec and I don’t know where the time has gone but I need to meet a man immediately” woman--- my first freaking out female. She was near tears through the whole meeting.  She showed up in her very corporate expensive black Armani pants suit with a silk blouse underneath and a Hermes scarf tied around her neck.  She was clutching a black Chanel handbag with a discreet handle throughout our entire meeting as if letting it go would make her lose her composure completely.  She was very pretty, about 5’6, straight red hair, pretty skin. She was very smart, went to Mount Holyoke for undergrad and Wharton for her MBA, very successful, owned her own corporate recruiting firm and was making a boatload of money, but she was all alone and she was sad, really sad.  She went on and on for awhile, rationalizing to me or maybe to herself how she got to be 39 and alone.  I wish she had come to see me or somebody like me when she was 29, not 39, and she probably wishes that too.  I want her to become my poster child to help convince women in their late 20’s and early 30’s that they are not too young to focus on their personal lives, they are not too young to hire me.  I liked her and I want to help.

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