Safety in Numbers

My business partner, Ellen, is a woman who terrifies me. She is a brilliant, petite blonde who is a total firecracker. She runs marathons; she has written articles for magazines; she has owned a boutique in the Village...and not to be a total name dropper, but she also dated Jon Stewart about ten seconds before he became famous. Ellen works out with a trainer three days a week at Equinox; she owns a spectacular apartment with panoramic city views; and her closet could easily be mistaken as an outpost of Bergdorf Goodman...filled with more Prada and Chloé than you could shake a stick at. She finishes the Sunday New York Times crossword puzzle every weekend with nary a mistake. She has a wicked sense of humor and is universally adored by all of our clients and co-workers alike. Ellen comes from a wonderful family who gave her the best education money could buy - along with frequent trips around the globe...to hone her shopping, skiing, and scuba diving skills to boot. Did I mention that she is always perfectly plucked, groomed, and manicured at all times as well?

The problem, you wonder? She is 40-years old and single. She has never been married, never had a child, and hasn't even had a boyfriend in the past three years. Ellen goes home every night and watches television alone; she cooks a healthy dinner for one to eat at her dining table by herself; and at bed-time, she crawls solo into her Frette-laden bed wondering things like "Is it too late to freeze my eggs?" and "Why aren't Russian mail order grooms available?"

Ellen's three dating options are as follows: 1) Going to bars in a low cut top 2) Paying a match maker $10,000 to find her a husband 3) Putting her photo up on every online dating service known to the world wide web. She chose option three and is thus a active member of Match, J-Date, and e-Harmony. In the past three years, she has endured countless blind dates and over time her desired age range has gone from 35 to 45, to 30 to 50, and now I think she is somewhere between 24 and 67 years of age for her "ideal match." God help her...another couple years of singlehood and Ellen might end up as the only girl on a dating website willing to date any man between the ages of 18 to 99, of any race, any religion, any income...with the sole requirement of having a pulse.

However - back to me, for a moment. The Muppet called. I did not respond. He called again. I picked up the phone the second time and we had a pretty good conversation. The guy really is charming and told me about his ups and downs of hosting 11 house guests at his Hamptons estate last weekend. He is going to the U.S. Open tennis final this weekend and he is heading off to a big charity event tomorrow. I must admit, looks aside - he is definitely not a loser. I am still not attracted to him, but I do recognize his finer qualities....which got me thinking back to Ellen. She would love him. O.K. to be honest, she would love pretty much anyone at this point - but then I started to imagine it. They could host me at their Hamptons house next Summer! They could invite me to join their table at a fancy charity ball at the Waldorf. They could even give me their U.S. Open tickets if they aren't using them next year as a little "thank you" for setting them up. It was perfect, really....I would love his lifestyle, but just without having to date him...and Ellen could have a "happily ever after" so I don't have to look at her and wonder if that will be me at 40? Alone...and illuminated by the glow of Match.Com on my laptop screen as I slowly go infertile! Argh! Banish the thought!

The Muppet ended our phone call by asking me out on a second date and I managed to convince him that I am so crazy busy, that if he wants to get together at all next week it would have to be a "group thing" and to please agree to join me and a friend or two....or else it would be two or three weeks before I am available again. He bought it and we settled on Monday night.

Ellen is totally up for trying the old "switcheroo game" and hopefully the Muppet will be easily volleyed into her court. We are going to try to find a second guy...a eunuch preferably, who can also join in on the game plan and can convince Muppet that I would be the mistake of a lifetime and that Ellen is the real catch of the two of us? Hmmmmm!

Would this, could this work? We all know the benefits of recycling cans, paper, and plastic - but men? Certainly worth a shot.

The Muppet Show

I am trying to figure out how much the personal taste of a match maker actually goes into deciding who to set one up with - as opposed to the match maker being able to truly decide what a great match is based on another individual's preferences.

My Chicago match maker is a gorgeous, young, totally put together brunette. She looks somewhat akin to Jaclyn Smith in her "Charlie's Angels" heyday. On the other hand, the New York match maker is a sassy, older, cosmetically enhanced woman with a serious Brooklyn twang to her accent. Imagine Fran Drescher, in her 50s, with straight hair and a year-round tan - and there you have her.
So, basically it seems that I have a Charlie's Angel and the Nanny both scouring the United States for my ideal man at the moment.

Incidentally, both are single themselves - which is good and bad. Good, because they are not tied down in a relationship and can be out there day and night searching for eligible bachelors and bad because maybe they are keeping the good ones for themselves? Who knows? In any case, thus far Jaclyn Smith has set me up with one gorgeous, smart, successful jerk and Fran Drescher has set me up with a successful, boring, mutant with an overly botoxed face.

The Nanny has two more men up her sleeve for me...one I went out with last night (and I will get to him in a minute) and the second is a Jewish gynecologist who lives on the Upper West Side. I do like the sound of a doctor, but a gynecologist is definitely an idea that I would have to get used to if we ever got past second base. God knows how looking at va-jay-jays every day can affect a man?

So, my date last night was interesting. Not a failure or a success. All I knew about this guy was that he is an entrepreneur, Jewish (again!), never married, and that he wants to settle down. That pretty much sounds like all of Fran Drescher's clients, but I suppose that is what we are all lining up for....to meet people who want to settle down. I just wish she hadn't say that up front. It just sounds weird - and desperate. Especially the concept of a man who is dying to settle down. I mean, what does a guy like that do in his spare time? Look wistfully at a copy of "Modern Bride" at a news stand and then blush and quickly look away? Does he browse for engagement rings on his own....just because? Does he see children in a playground and hear some sort of biological clock ticking inside of him? Ugh- I certainly hope not!

In any case, the entrepreneur showed up at the restaurant perfectly on time (one point.) He had a reservation (another point) and he offered me the seat with the view (he is on a roll.) I must admit, that I was perfectly under-whelmed by his appearance. He had a slight build, he wasn't really tall, his nose was huge, and his eyes were large and bulging out of his skull. He was also clearly at the back of the line when God was handing out "shoulders" because he certainly didn't seem to have any. In fact, this man looked almost like a human Muppet. He was sweet and cute like a Muppet - but there was certainly nothing sexy or overtly alluring about him physically.

The dilemma was this....he was really nice. He was courteous, well natured, and thoughtful. He was bright and has clearly made himself a small fortune. He has a house in the Hamptons with a pool and tennis court; he just finished renovating his large apartment on the Upper East Side - and best of all, he has done well enough to essentially retire - but he has a few more businesses that he would like to start up - just for fun...at least until he has a family. The Muppet was truly a respectable set-up. However, he didn't make me laugh really hard, I didn't feel any physical chemistry with him, and he reminds me of a stuffed animal when I look at him.

The Muppet made me question if I was really shallow because I could honestly care less if he calls me for a second date based mostly on his looks (or lack thereof.) However, looks should count for something? I suppose the answer is how much and when (if ever) can you get past wanting a super hunk and start finding guys like the Muppet attractive.

Oh - I just wish I could like this guy. He seems great...but I am just not feeling it. He said he would call after the Labor Day weekend, so we will see? Maybe he wasn't feeling it either and I am off the hook?

Reality Bites

Hedge Fund guy sounded gorgeous on the phone. His voice had a perfect pitch to it that leaned a bit to the gravelly side - which is totally sexy. We had a great conversation and so I was totally excited about our date set up by the matchmaker in Chicago.

He placed his call to me from the Windy City just before getting on a plane. He had to host a board meeting in his Greenwich, CT office and then he had a meeting in Manhattan. He was able to slip me in for a quick dinner after his last meeting and before getting on another plane to go God knows where the next day. He sounded perfectly in control of his hectic life. He didn't try to seem overly important and considerately booked a restaurant across the street from my apartment. I liked him already. Well, the only irritating thing was that he double-checked that I would convert to Judaism if it came to that ("that" meaning "marriage", I suppose)...and I quickly agreed. If Charlotte on "Sex & the City" could do it to marry Harry, then I am sure I could too? I think.

Hedge Funder was the kind of blind date you dream about initially. He looked exactly like Michael Douglas. Not Michael Douglas of today, mind you - but Michael Douglas of the 80s (Wall Street, Romancing the Stone, you know what I am talking about!) - he was just plain gorgeous. He was perfectly on time and wearing what was clearly a ridiculously expensive suit. We were offered a small table and he asked for a booth - and we got it - despite booths only being for parties of four or six. Way to take control, Hedge Funder.

We ordered a bunch of appetizers and some cocktails. We decided to hold off on ordering the main course until later. And then the Spanish Inquisition begun.....Hedge Funder had 10,000 questions and he shot them off at the speed of a military assault rifle. He prefaced the Inquisition by saying that he was not wishing to waste anyone's time and that he has a good idea of what he wants and what he is looking for. I guess you could call me warned?

He asked if my parents were divorced (yes); Do I have a close relationship with my Dad (no); What was my longest relationship (3 years); have I ever lived with anyone (yes); Am I an only child (yes, but only because my brother died when we were both in our late teens); Do I have more male or female friends (about equal); How many children do I want to have (1-3); could I raise children in Manhattan (maybe); City I would like to visit next (Prague); and on and on and on....until finally he asked if I had any questions for him. I just looked at him and laughed.

What was he thinking? This was a date not an interview....or was it? It was supposed to be an easy exchange of information - not a Q&A session. I didn't prepare a list of questions before meeting him - I was too busy fussing over what to wear than thinking about specific topics of conversation before I had even met him. I stammered and asked if his parents were still married - even though I really didn't care - and they were (of course!) for the past 47 years and they were still madly in love. Hmmmm, O.K., good for you, Wally Cleaver.

He then did the absolute unthinkable. Our second round of drinks had just arrived at the table. We were not even half way through our appetizers - and he threw $80 on the table and stood up. I remained seated looking up at him on the other side of the table with my mouth slightly agape and he said "This is not going to work. I have a car waiting for me outside and I need to go." He wasn't kidding and he picked up his jacket and started putting it on while I remained seated staring at him incredulously.

I asked if he was seriously just leaving - and I regret asking that question. He turned and said to me "Listen, having divorced parents - you didn't have a good view of what a healthy relationship looks like from a very young age. Clearly, you have been abandoned by the most important men in your life from your father leaving the family after the divorce and by your brother dying. Even though you "seem" normal, I am quite sure that you have serious issues with men as a result of your background. I am sure a lot of men will be interested because you are pretty and smart - but I doubt anyone will stick around. A girl like you just doesn't have the skills to be successful in a long term relationship. Sorry!" and with that - he walked out.

I felt sucker punched. He just left me in a crowded restaurant, with three plates of hardly touched appetizers, two full drinks, and a small stack of $20s on the table. I felt like there was a huge neon arrow hanging over my head pointing down at me with the word "LOSER" written right above the arrow, blinking off and on. The waiter scurried over quickly to the table to ask if everything was O.K. I suppose everyone within earshot had heard what he said. I took a few more sips of my drink and had a french fry while I tried to gather up my dignity and regain feeling in my legs so I could get out of there and far, far away from the apologetic looks of strangers after my rather public rejection.

I walked back home burning with shame and wondered if anything he said had any truth to it. Obviously, it is beyond my control that my parents marriage didn't work out. I always wanted a good relationship with my father, but he married a much younger woman and had a new family that I am just not a part of. My brother died of cancer and that was neither his fault, nor mine. I suppose the hedge funder wasn't saying these things were actually my fault - but more just the fact that they had happened and thus I am damaged goods, due to history that I had nothing to do with. I am a product that no one will want and I am incapable of achieving the picket fence dream, well...according to him, that is.

The worst part of it is that I finally met a guy who is gorgeous, brilliant, successful, well-traveled, athletic, with great personal style....who really wants to settle down and have kids and he literally looked at me, right in the face, and said that I wasn't even worth sitting with for a main course, let alone dessert, or (gasp) an entire lifetime together.

This is the first time I have ever been abandoned in the middle of a date and I seriously hope that was the last time. Ouch.

Jeepers Creepers

My first "match made" blind date was with the New York match maker's guy...the real estate developer. He sounded a little creepy on the phone, but he did suggest to meet me in person at Giorgione - so he can't be that bad. The food there is great and so he does have a modicum of taste, at least.

I arrived first and exactly on time. I know I should always be ten minutes late - as no one in New York is ever on time. There was no reservation in his name, the restaurant was packed, and there was a one hour wait for walk-ins. This was not boding well. Hopefully he has some pull with the manager or something?

He showed up 20 minutes late - complaining of traffic. Granted, he probably forgot that he told me where he lives and so I know for a fact that his apartment is a mere four blocks away from the restaurant...but I will let the little white lie pass. Who doesn't lie about being stuck in traffic when late? I then asked him if he had a reservation, knowing full well that he did not, and he started to look nervous. He rushed over to the hostess who then informed him the same thing she had already told me. Fully booked...and we would have to either go somewhere else or wait for an hour...or more. Nice job, loser. I had actually been looking forward to eating at Giorgione more than I had been looking forward to meeting him, so I guess that is what I get for thinking such evil thoughts.

He stood there at a loss and I suggested we head over to Giorgione 508 around the corner - the more casual branch of the same place. We went out into the rain and as I suspected, 508 was completely empty save a few tables because it is really more of a breakfast/lunch place than a date spot, but whatever. At this point, I just wanted to get it over with.

Real Estate guy was boring, hesitant, and had zero game. On his second glass of wine, his neck started to go all red and he had no problem eating off my plate without permission. Ugh - disgusting. If I had wanted to share, we would be in either a Chinese or a fondue restaurant.

On closer inspection, I was finally able to put my finger on what exactly was wrong with the Real Estate guy physically. I mean, he was tall enough, attractive enough, and dressed O.K. (most likely Banana Republic/Kenneth Cole kind of guy) - but there was something definitely off and then it hit me during dinner what it was. His eyes! He had old eyes....a little hazy, yellowish, blurred irises - but oddly taut skin on his face. He was completely over-botoxed and there was no way this guy was 40. In fact, he might have even been 60 with a face lift. I swear.

My first impression of him from the phone had been accurate. He was creepy. Even the waiter didn't like him that much. I can totally imagine this guy on Dateline "To Catch a Predator" series or some similar show.

I just have one word for this experience.....NEXT!

Matchmaker, Matchmaker Make Me a Match

I finally picked up the phone and called both the matchmaker in Chicago and the one in New York. They were both very happy to hear from me and they both had my ideal man all ready and lined up and ready to go. How convenient.

The New York match maker has a 40-year old real estate developer who lives in a full-floor SoHo loft as my first set up. He works in the family business, he loves to travel, and he collects art. He is dying to be married since yesterday and have children. He has three brothers who are all happily married and all he can think about is marriage. He is Jewish, but doesn't care that I am not. He likes tall blondes...and particularly one who is ready to start a family immediately. I mean, I suppose I could physically have a baby within the next nine months - but that whole starting a family now thing sounds a little strange. That said, I agree to meet him anyway. Why not? I could do worse...and I have.

The Chicago match maker has a 43-year old, hedge fund owner, who is 6'4", stunning (according to her), witty, never married, and has homes in Chicago, New York, and Greenwich. He is Ivy educated, he competes regularly in triathlons, he comes from a wonderful family, and he wants to settle down as soon as possible. The catch with him is that he is Jewish, but not attracted to Jewish women, so he ideally wants a WASP who is willing to convert. I guess I could convert for the right guy? I mean if George Clooney wanted me to become a Branch Davidian to marry him, I'd probably fill out the paperwork and get started within five minutes on the conversion process, so "yes" - if he is "George Clooney Hot", then perhaps I will change my religion. What the heck?

And that is that. The Real Estate guy and the Hedge Funder will be given my number today and the dates are imminent. I'd put my money on the Hedge Funder as being the more interesting one, but you never know? I've been wrong before and hence I am writing this blog!

Plan C

About a year ago, I had read an article in Cosmopolitan Magazine (or some similar magazine?) about matchmakers and I had decided to call the top one in the country (based in Beverly Hills) and see who they had for me. It was a miserable experience and a story for another day.

However, about six weeks ago I decided to try two of the other top matchmakers in the country because maybe I just had bad luck the first time? I can't afford to risk my professional reputation by being on Match.com - and so this seemed like a more discreet means to the same end.

The way they work is that successful, eligible men who truly want to settle down will pay these people between $10,000 to $50,000 per year to be set up with attractive, smart women who also want to settle down. Luckily, the matchmakers decided to take me on as "inventory" which means that I'm in their little black book for a man who is looking for exactly my "type." To be considered as "inventory" one has to be considered generally pretty, have a college degree, be physically fit, not previously married, no children, and under the age of 35.

I get to be set up for free as I am a regularly requested "type." There is something that feels slightly hooker-ish about the whole thing, but what are my options? I can't stand the bar scene, or the clubs, and I am busy building a company in my spare time to pay my mega-mortgage! Where on earth am I supposed to meet my greater or equal with limited time and a complete disdain for a rocking social life echoing my college days? Believe me, I have tried taking classes; and going to academic lectures; and going to sports events; and volunteering;with no luck. Every place one recommends to meet men, I show up....with half the female population of New York showing up right next to me. I sadly even tried a sports bar once with a girlfriend thinking that would be like shooting fish in a barrel. The bar was full of men - but there was a game on about 30 televisions scattered around the room and my friend and I may well have been bar stools for all they noticed.

Anyway, I have digressed....the matchmaker it will be. There are two companies...one in New York and one in Chicago. I am leaving no stone unturned. If I decide that I want to have them look for me, for the type I want exactly, then I have to pony up thousands as well. At this point, until I hit 35 and am no longer eligible to be set up for nothing....I will remain in the black book of two of America's hottest matchmakers. Those matchmakers are my "Plan C"....and I absolutely intend to use them should Bambi continue to play this stupid game.

Do you really want me to call in the Dating Guards, Bambi? Because I will, really.