I Tried Online Matchmaking...It Doesn't Work.
- The Curious Columnist

- Sep 5, 2023
- 4 min read
Updated: Feb 4
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BY JENNIFER SILVERMAN

Welcome to the second installment of my "Matchmaker, Matchmaker" saga.
If you missed Part 1, click here to catch up on oodles of Fiddler on the Roof references and my initial misgivings about whether or not online matchmaking actually works.
Exploring the resurgence of the matchmaking tradition in my first post rendered me rather curious about modern day Yentas.
(Not familiar with the word, "Yenta"? A colloquial term, a "Yenta" is a matchmaking busybody a la the classic musical, Fiddler on the Roof. Matching mates for marriage is Yenta's divine calling.)
Intrigued, I decided to give it a go and register with an online matchmaking service.
Since I initially fancied the exercise a dating experiment, I opted for a passive approach. My matchmaking membership of choice included only a dating profile to which matchmakers could match their clients.
(Frankly, I didn’t anticipate a boatload of matches with the passive route – especially considering my decision to not have kids and insistence on maintaining my small-town primary residence.)
After I completed the questionnaires, I frankly forgot about my “research.”

When a matchmaker contacted me out of the blue a couple weeks later, it took me a few beats to recall my matchmaking experiment.
A barrel of surprises, both the matchmaker and her client reside oceans away from my Floridian abode - in Ireland.
As it happens, it’s apparently commonplace for matches to relocate if they hit the match jackpot. (Who knew?)
The matchmaker’s client had apparently already approved my profile, so it was up to me to agree to the introduction – or not.
"Maybe he has a haunted family castle. That could be fun," I thought.
"Perhaps he has an accent. I love an accent," I considered.

When I reviewed his images, I came across no castles in the background, and he was not the Pierce Brosnan type conjured up by my imagination.
A fellow late 30-something, he worked in international finance, could live anywhere, and appreciated the arts.
However, nothing in his profile really resonated, and he bore a striking resemblance to Danny DeVito...I admit that I was reluctant to accept the match.
Reality rarely looks the way we envision it, but I feared that this reality was several dozen bridges too far from Pierce Brosnan.
On the other hand, a professional matchmaker chose me for this guy. Could she see something I didn't?
I subsequently gave some advisors a ring to pose the age-old question, “Am I too vain?”
“Am I a jerk for absolutely judging a book by its cover, and not giving a guy a chance?”
Afterall, the majority of single men are seemingly in pursuit of a metaphorical Cindy Crawford, but they don’t seem to understand they're not Richard Gere.
Was I being just as narrow-minded with my superficial reaction to my match?
To my surprise, all my gurus recommended that I decline my matchmaker match and be true to my own dating preferences.

Some ladies would undoubtably be thrilled with this accomplished, presumably very nice, Danny DeVito doppelganger, but alas, DeVito is not quite my style.
Did I make the right call?
I think so. Like it or not, we all have initial reactions to other people, and most of the time, they tend to be on-point.
Going with my gut rather than ignoring something that didn’t quite jive for me may seem judgey, but at least it’s honest. And honesty is likely in the best interest of all parties involved.
The following day, I received another match. Bachelor number two was an athlete who evoked Mr. Clean vibes. Alas, he was also not my cup of tea.
Of course, no match will be perfect, but neither bachelor possessed that je ne sais quoi that compelled me to take the plunge.
Despite the wrong fit with matches one and two, my matchmaker encounter was pretty fascinating.

So, I switched my membership type from passive to active and now have a couple matchmakers working on my behalf.
Will the matchmakers discover my Mr. Right?
Will the next DeVito or Mr. Clean be too good to pass up?
Beats me.
I do however have a hunch that “Matchmaker, Matchmaker” part trois is imminent. Stay tuned.
UPDATE - After declining several matches, I finally accepted one. Then I found myself in a matchmaking soap opera. For the funny installment of my matchmaking story, click here.
P.S. - By the way, if you're wondering if digital Yenta matchmaking really works, in my experience, the answer is no. I'll tell you all about it in "Mama's Boys - A Definite Dating Don't?"
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