74 of my friends were single and looking. So 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.














This problem is interesting to me both as someone who was successfully matchmade, and as a therapist. In my personal experience, a friend texted me "I never do this, but you should really meet my friend x" and x is now my wife. But with clients who are highly eligible but struggling to meet a partner, I share your sense that there's something inner that's getting in the way of their meeting the right person, rather than something outward and logistical. Personally, I did do a lot inner work before I met my match.
Everyone I dated I met in a shared context with spaced-out repetition, you met your girlfriend through your blog. Only insane person would keep going on coffee dates for the time it takes me to develop a crush, so instead I expand my surface area of luck by showing up in more contexts.
Just host things and invite your friends who don’t all know each other and see what happens. Christine has written it takes her friends meeting about 8 times to get a buy-in and become friends, I imagine it’s more for a spouse.