74 of my friends were single and looking. This made me think… what if I matchmade them?
The first step was to keep a list of all of my single-and-looking friends. So I asked friends if they wanted to be matchmade:
And added a new tag to my friend database to stay organized:
But soon I realized that when you ask someone for their type, they usually reply with vague adjectives. “Kind.” “Funny.” “Smart.” I needed to find a better way to match people.
When I was single and asked friends to matchmake me, I gave them a list of examples of exes, crushes, and friends I almost dated. Within seconds they’d exclaim: “Ohhhh, I see your type! Hm, do you know so-and-so?” Their suggestions were surprisingly accurate.
So I started asking my friends for examples too.
It’s easier to think of “People like Alex” than “People who are kind”.
Matchmaking got easier after that: over the next several months, I made several dozen 1-on-1 matches.
But something weird kept happening.
Friends would be excited about some of the matches and then… not schedule the date for weeks? Or months?
Other friends would go on a first date or two, realize “dating isn’t a priority for me right now”, and stop.
It was quite frustrating. But I didn’t know what to make of it, so I kept matchmaking.
I also doubled down by experimenting with other matchmaking methods, including running public events and inviting friends to parties outside their social graph. But these too were less effective than I hoped.
Men complained that it was “too hard” to interact with women in group conversations.
A single friend I brought to a party had a hard time even standing near cute guys…
I thought, “Maybe she just needs more matches?”, so I posted a twitter classified:
Over 30 men reached out, including founders of companies you’ve heard of and people with Wikipedia pages.
But… she only went on dates with four of them ¿
Later, I tried the twitter classified for another friend:
Again, lots of interest from men who seemed promising… but, somehow, nothing came from it?
At this point, I’m reminded of a matchmakers meetup I ran several months ago:
At the meetup, I met someone who had professionally matchmade six marriages (with more than 7 kids so far!), and many more relationships.
Surprisingly, despite her success, she had actually moved away from matchmaking and towards helping people get ready to get married.
The significance of this hadn’t dawned on me until just now.
Why had she moved her focus?
Because most people who ask for matchmaking aren’t ready to get married.
And one way they avoid getting ready?
By asking to be set up instead.
Oh no.














What does getting ready to get married look like, from your perspective? I'm married, but I'm not sure I did much to prepare other than babysit for a year to make sure I liked kids and telling my 4 boyfriends at the time that I wanted to get married in the next couple years.
You write:
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Over 30 men reached out, including founders of companies you’ve heard of and people with Wikipedia pages.
But… she only went on dates with four of them ¿
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Wait, isn't that an amazing success rate? You helped someone get four dates who were preselected to be likely good matches! I'm not sure what more you expected.
Every pipeline is a funnel, and there are lots of reasons to expect the jump from "send a three line interest email" (requires 30 seconds of "that sounds nice" impulsiveness) to "meet someone in real life" (requires clearing actual time in the calendar, logistics) to be a strong filter.
It sounds to me like you did awesome.