My Date With a Matchmaker

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When I met the matchmaker, I had just moved into the city after a long absence. I was way over budget renting a new place, having to buy a car, and not getting a raise I banked on plus the downturn of the economy. So, I decided to start a business, of all things.

I remember distinctly having to “put myself out there,” which consisted of me attending many networking events and parties. Mind you, I never really did much business at these events, it was mostly sanctioned flirting with all types of women alike, maybe getting to biz if it worked.

I made a ton of friends and a few enemies this time in my life; something I don’t regret in the slightest. But I will never forget the day I ran into this phase of my life.

One of the events I attended started off innocently enough with me schmoozing with a very young woman. While I knew that I was in the conversation for personal reasons, she immediately pushed back and never let me gain any ground. But she was flirting with me so much, but something was off. As it turns out the whole act was a ruse.

She told me that she worked for a ‘matchmaking’ company. We are all familiar with ‘matchmakers’, most of the time, it’s your female friends hooking you up with their single friends, because that is what girlfriends do. But of course, the adage is true — “Matchmaker, Matchmaker, first make me a match!”.


This was the case with this young woman, pitching me this service as if it was something I desperately needed. The whole premise of the matchmaker service was to take the hassle out of dating. Their pitch was that they would find quality dates for you, make the introductions, schedule the date and handle venue logistics. If it seems too good to be true, yes, it is. I was under a vague impression that companies like hers were urban legends. This was before Millionaire Matchmaker and other shows like it came to prominence, and I admit that I was clueless about the whole thing. Later on, I came to realize there were plenty of companies in Chicago, under similar names/constructs.

However, this was different. I was offered a ‘free’ date for this matchmaker company. Looking back, this was my first mistake, because there is no such thing as a free lunch. I felt pretty confident in my dating ability, but I was of the mindset that I would evaluate all opportunities. I was single at the time and I figured I really had nothing to lose. That, and it wouldn’t cost me anything, save for the date itself.

But of course, I was wrong about that. Dead wrong.

For starters, there was the date setup. I got a questionnaire that read more like a background check. Right down to ‘how much do you make a year?’. Also, because Googling people on the internet was popular, I basically had to go through a middleman, or middlewoman as it were, to facilitate the date. This was to prevent backing out if you found out something about your potential date beforehand. They only gave me some very vague information in the first email — name, age and some quick tidbits. The was no photo either. I didn’t care mostly for this info because I knew I had to meet her in person to get the real story.

The company set up the date to be dinner for two in a restaurant in Old Town. I was told that the restaurant would specifically cater to us, and I had assumed that was because the restaurant might have paid for us to be there. Reservations were made, confirmation emails were exchanged and finally I got the woman’s phone number, a mere four hours before the date was supposed to take place. I got there early because it was after work and close to my office, and when I arrived there was no ‘special treatment’. I just got a table and sat down. Meanwhile, I remember being more nervous than usual, basically because I was going into this blind. I had no idea what to expect. It was in a public place, so I figured she couldn’t be a serial killer.

Then I got a call. She was going to be late due to traffic.

At first, I thought this was a major strike against her, as if it were a job interview. I got there early myself and was a bit bummed, because I was sitting alone at a table. The waitresses were nonchalant about it all, but I felt it was obvious why I was there. As a cardinal rule for first dates, I didn’t have any alcohol, but significant time had passed since I got the phone call, so I ordered a drink, silently confirming with myself that this date was already over. I was just being polite to stick around until she finally got there. I got another text that she was parking the car about an hour and a half later, and then 20 minutes later she arrived.

She was an attractive woman, which I was surprised about. There is always a question in my mind when I go on dates like this. “So, if you are so awesome, why are you paying someone to find you a date? What’s wrong with you?”. Of course, this would be blatant hypocrisy on my part, so I tried to reserve judgement the whole process. In the initial conversation, she also sounded intelligent and put together, so I relaxed a bit, maybe changing my mind about canceling the date.

Then of course, it took a turn for the worse.

She started firing off a ton of questions. Not getting to know you type questions, but very interrogative type questions. She also got very aggressive and controlling of the conversation. I remember being appalled that how can she have these questions when she was two hours late to the date herself? At some point during the barrage, I disengaged from the conversation, being too angry about what was transpiring. I did not want to respond in anger and drag this on further than necessary. I also got the hint she was not into me either at a certain point. At the end, I paid for everything, exchanged hugs and drove off into the moonlight.


It wasn’t a complete waste of time mind you, but I just remember being a little distraught for all the questions. I was hoping it was a one time occurrence, maybe she just wasn’t the right girl for me.

The matchmaker called the next day, looking for feedback. I held no punches in telling her the truth, how the date was late, very aggressive and that I didn’t like her all that much. She replied that my date had similar feedback to what I told her, which I found jarring. She also mentioned she had someone else she wanted to set me up with. I tacitly agreed to the date, hoping this girl wouldn’t be like the last one.

The same process occurred for date number two, except this time, it was at a pub that was a little more low-key. I had my guard up, remembering what had happened previously and hoping that things would be better for the next one.

The date actually went okay. The date showed up, and I felt had a sense of humor about the whole thing. We talked about more light-hearted topics and I felt we really connected. So, we exchanged a hug and a kiss at the end. I felt vindicated and ready to shout from the rooftops how well this all worked.

Of course, the follow-up with the matchmaker the next day confirmed everything. It went well, and she wanted to see me again. That was good. I remember the conversation being somewhat of a sales follow-up call, but I resolved to just cut them off. After all, I was a happy customer. I was asked, just like in recruiting, if I knew anyone else who wanted to get involved. I politely declined.

I went on a second date with ‘the one’. With the pressure off and pleasantries exchanged, the date went much better than the first one did in terms of getting to know one another. I was just happy to be on a second date with someone who was independent, held her own and I could aspire to.

But that was the problem, it almost seemed too easy. It’s a kind of paradox, you want your dating experience to involve some emotional turmoil so you can backwards rationalize your irrational behavior later on at the wedding. But when it’s too easy, or not a lot of serendipity, the mind wonders. It almost feels like you cheated death for some reason.

My suspicions unfortunately came true. At some point, the ‘buy-in’ question occurred. I don’t know who got to the thread first, but I remember asking her how much she paid to be a candidate in the matchmaker program. She responded with a number in the five-figure range.

I remember having the sickest feeling in my gut after hearing what she said. I remember smiling and nodding off about how much I paid, which was zero. I never told her the amount and got away with the assumption that I paid the same amount.

This made EVERYTHING that happened with this company and why I was aggressively recruited make sense. They probably didn’t have anyone in the database that matched her request at the time of acquisition. I was basically a rope-a-dope, fostering the charade along. The first date’s aggressive nature made sense too, I’d be asking that many questions if I had committed that much income to solve one of life’s oldest problems.

With this knowledge, I couldn’t consciously continue dating her. I don’t know what price point I would have stayed, but it just felt morally wrong to take advantage of the situation like this. I made a graceful exit from the relationship. I offered to fix her PC, which put me in a different light for some odd reason, and I walked away quietly.

The company came calling again not long after, offering me the same deal, to which I also gracefully declined. I couldn’t honestly do that again, knowing what role I played in this whole game. Thankfully not too long after I got into a long-term relationship with someone of my own accord.

Needless to say I had a very sour taste in my mouth about professional matchmaking. I learned later some of the major dirt about the industry through an insider, to which I dare not repeat. I can only recount my own experience. It made me redouble my efforts to improve my own dating life to the point that I’m not on the other end of the deal. I don’t judge people who engage with a matchmaker in the least. It does provide a much-needed service to those who are unable to find someone to share their life with. And there are plenty of options out there to go about finding someone. However, unless for some reason I lose my mental functions, I think my time and effort can be spent on other things.

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