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This post is part of a series about my own personal dating experiences before I met and married Marc.  I may be a newlywed now, but just a few years ago I never thought I would be anything but single, and I hated it.  When I was struggling I didn’t feel like there was anyone who could truly understand.  I was single, I didn’t want to be single, but I also wanted to be happy in my present life.  My hope with this series is to give people who feel the way I felt hope, no matter where their lives might take them.

The first two entries in this series were pretty serious and kind of heavy.  Marc, especially, didn’t like reading them because he feels badly that I went through the things I did.  But I’ll tell you what I told him: if all those struggles meant that one day I would find someone as kind, compassionate, loving, good, funny, real, and true as Marc, then it was all worth the wait.

But in the meantime, during that wait, so many ridiculous things happened!  I mean, what adult human who has been single for at least a week doesn’t have some crazy dating story to share?  None, because it isn’t possible.  Especially in New York City!

I’m not even sure where to begin with mine.  But here’s a start—how about the matchmaker from hell?

Yes, I went to a matchmaker.  I actually went to three different matchmakers in New York City, to be honest, but the other two were nothing like this woman.

She claimed to be the original Millionaire Matchmaker with hundreds of success stories.  But despite all that grand success she was still on Groupon, which is where I found her.  Okay, I know what you’re thinking!  There are certain experiences where discounted prices are amazing.  However, things like Matchmakers and Botox should never be one of them.

But I figured, what did I have to lose?  For around $100 (yes, that was the discounted price) I would meet with this woman along with a handful of other single ladies and she would “get to know us” to see if she had anyone with whom we could be set up.

Here’s how it typically works with matchmakers like this:  The men are the paying customers and the women just need to find a way to get entered into the matchmaker’s database, aka the pool from which she will pick the women who get setup with the paying customers.  It’s stupid and archaic and when I look back on it now, pretty damn embarrassing, but I was 32 and didn’t think I had any other appealing choices.

So, I bought my discounted ticket and arranged my group time to meet with this matchmaker.  I should also mention this meeting took place at a fancy themed bar in New York City and once we arrived we were required to buy two drinks minimum (for a 30-minute meeting).  I said I just wanted water and was told that wasn’t an option.

At that point I should have run.  Far, far away.

But I stayed.  And with my super fancy drink I sat down with the nine other women and our matchmaker.  She had required us to fill out a questionnaire and submit pictures ahead of time, so she began by doing a roll call.  This roll call involved her calling out your name, looking you up and down, and comparing you to the picture submitted.  A couple of the women were then told they needed to submit new pictures because they no longer looked as good as the ones she currently had.

You seriously can’t make this stuff up.

She then began asking questions of specific women.  Things like, what are your deal breakers?  When was your last relationship?  Can you lose ten pounds?  Would you consider hiring a professional photographer to take your picture for the database?

Yup, still can’t make it up.

For the most part I was not in her line of fire.  The only question she asked me was if I had a height requirement since I’m so tall.  I told her I preferred 6’2 and above, and she moved on.

After about 20 minutes of this nonsense I had mentally checked out.  I couldn’t listen to her critique a woman’s weight or clothing choices any longer.  But then she decided to address the entire group.

I would say at least six of us were over the age of 30 so she suddenly felt the need to share with us some pearls of wisdom.  What she said next, I will never forget.

According to the matchmaker, “I need to know all of your baggage.  It’s actually impossible for a woman to still be single over the age of 30—without ever having been married—and not have a whole bunch of issues.”

W. T. F.

I look back on it now with mixed emotions.  Part of me wants to laugh in her face, another part wants to angrily tell her where she can shove it, and another wants to kick her in the shin.  But a really hard kick.

At the time I was incredibly vulnerable, so my reaction was completely emotional.  I made it through the final few minutes of the meeting, threw some money at the bartender for the second drink and got myself out of there.  I couldn’t even figure out where I was walking or how to get back to my apartment.  I just knew I had to get away from there.

That’s when I called my friend Lucy and just started crying.  It’s a proven fact that you aren’t a true New Yorker until you’ve walked down a Manhattan street openly crying while not giving a damn.

When I told her the entire story Lucy couldn’t help herself and started laughing.  That made me begin to see just how insane the experience was, and how much it didn’t deserve my tears.  After a while I calmed down and made my way home.

I vowed I would never meet with this matchmaker again, but I remained in her database and would hear from her occasionally.  Usually it was to ask if I was going to be in the Hamptons that weekend to see if I could be date bait at one of her poolside “mixers”.  When I told her I worked weekends she said I would need to quit my job if I ever wanted a relationship.

About two years later she called to tell me she had found my future husband.  According to her he was absolutely perfect.  A successful finance guy who had never been married and was finally ready to settle down and have a family.  And because I was now 34 and nowhere closer to finding a date my selective amnesia took over and I actually agreed to meet him.

But crazy is crazy, and selective memory or not, it will eventually seek its vengeance.  And let me tell you, this chick was crazy.

My “future husband” turned out to be roughly 60-years-old (of course he was finally ready to settle down!), retired from his finance career, living in a different city than New York, shorter than me, and did I mention 26 years older???

We went to one dinner.  It was like an old friend of my dad was in town on business and agreed to take me out, so he could report back to my parents that at least I had one decent meal that week.

It wasn’t the worst experience of my life—he was nice—but it couldn’t end fast enough.  Fortunately, I had an excuse to leave early and he only shook my hand as we said goodbye.

When the matchmaker called to ask how it went I told her he was way too old for me and I was very uncomfortable with the situation.  She feigned actual shock and asked how I knew how old he was (as the women/unpaying customer we were never allowed to ask questions).  I told her I simply looked at him.

And that was the last time I ever spoke with her.

Thank god.

But that experience was leading to something.  That and a million other crazy things I went through were all pointing me toward something better, I just had to find it.

Even if I hadn’t met Marc I was still getting myself to a point where I finally accepted my relationship status as single.  For me that took many years and countless ridiculous stories.

But as I told Marc, it was totally worth the wait.

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