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.

About | Twitter

Unhinged expectations

Problem: Wanted to run a social aggressiveness event without worrying about hurting anyone’s feelings.

Solution:

By writing an intense event description, the right people self-selected themselves in — and out — of the event. This is essential for any unusual event. Another example:

(More examples.)

‘Honorable’ invites

Problem: Wanted to run an intentionally awkward flirting party, but the sex ratio in the SF network isn’t great; also many women were skittish about rando men.

Solution:

I consulted a commitee of 10 women to plan this event well, and they were much more excited about the prospect of this event with Honorable Invites than without.

Plausible deniability

Problem: Wanted to run an event where truly controversial takes could be shared openly. So people needed to feel safe doing so.

Solution:

Examples of what may or may have been on the slips:

• “Only white men can save us.”

• “Intelligent people are worth more.”

• “Bestiality is good actually.”

That said, I don’t know if this mechanism actually helped directly, or just attracted the right attendees and repelled the wrong attendees.

Group debriefs

Problem: I like running unhinged events that could go horribly.

Solution: End every event with a group feedback and story-sharing.

More events

You’re invited

Subscribe to events: chrislakin.events

Many horror events are possible, like Intentionally Awkward Flirting

Party where avoiding eye contact = JAIL

The purpose is like that of horror movies: to feel (pain).

It’s a reliable way to get interesting people together.

Some past events

Authentic relating without the authentic relating junkies:

The first intentionally awkward event:

Dedicated post about eye contact events.

Dedicated post about dog massage.

Get invited to the next one

San Francisco: chrislakin.events

Acknowledgements

Thanks to Shailen, Archana, Barak, Skye, Alyosha, Shaul, Leo, Maeby, Hattie, Gytis, Asuka, Luke, Max, Pranab, Jinny, Adam, Myles, Elena, Lika, Georgia, Doug, Lulu, Shiki, Stag, Ethan, Kipply, Kishan, Space, Soryu, The SF Commons, Banu, Jason, and more for helping make these events fun.

Related

A friend and I wanted to run an event where controversial opinions could be shared openly. Examples of what may or may have been on the slips:

• “Only white men can save us.”

• “Intelligent people are worth more.”

• “Bestiality is good, actually.”

We also advertised the event so only a certain kind of person showed up:

It was life-giving to be in an environment where I could say what I think without second guessing myself —Participant

To subscribe to future events: hit “Subscribe” on this page.

Related

That said, I didn’t want eye contact to feel forced, I wanted it to feel genuinely comfortable. How?

First, an experimental workshop

For most attendees, the first meditation was enough. Here’s what one said:

The transition moment for me was [the first meditation]. I thought about a cat that I once lived with, I would be proactively looking him in the eye and saying how much I love him hahaha. That felt very natural and easy. Then, with that feeling I was able to start appreciating the people that I was having eye contact with without the awkwardness. Also, more curiosity aroused as well!! (Since for me it’s easy to look at something for a long time when I’m really curious about it.)

For others, a few additional activities or a quick 1-on-1 were necessary. But by the end, no one had trouble making infinite eye contact.

We stress-tested ourselves with one-on-one conversational eye contact, silent eye contact, group conversational eye contact, and everything else we could think of. We went undefeated. Constant eye contact was completely comfortable now.

the vibes of this event reminded me of a molly party I was at last week

Since your event [two weeks ago], I'm far more aware of both the eye contact I give and the eye contact I receive. I'm especially aware of how good I feel when I receive it and so I've been trying to give it out more, anticipating that others feel the same.

The 100% eye contact party

For the party to work, it needed an enforcement mechanism. Without one, attendees would forget about the eye contact and it would devolve into — god forbid— a normal SF party.

So I designed a dictatorless dystopia:

Three strikes and you must go to jail. One strike each time you're caught not making eye contact during conversation. Please give strikes to autist offenders. Please send three-strikers to jail.

​To attain parole, you must make silent, present eye contact with another jailee for two minutes straight. […]

With a catchy image:

and a catchy title:

Finally, I sent it to my events list.

We set up the jail…

And 40 people showed.

Began with similar activities as the earlier workshop. It was more difficult to do with >2x as many eyes… and some people needed extra help so I helped with them 1-on-1… but on the whole it worked!!

Videos

Group eye contact was so goofy!—

Reviews

The design made it easier to access a range from flirty and fun to deep and serious. The event was higher intensity by default.

It was super super intense. I remember desperately wanting it to be over, but it was still a lot of fun. My first 1-on-1 conversation was very fun and lasted over an hour.

The jail was a hilarious idea and added excellent vibes.

Eye contact was kinda hard and I went to jail a lot… but I had a lot of good conversations, and the party felt very intimate.

I liked experimenting with eye contact from different heights. I made eye contact while looking down for almost the first time and felt stronger.

I felt very connected to everyone afterwards and felt very open, present and happy.

To be invited to future events like this, subscribe here.

Thanks to Leo, Shaul, Lika, Eliza, Jinny, and The SF Commons for making these events wonderful.

I’ve run massage events in the past…

…but only for humans!

The skills do transfer:

With a goal in mind, I made a request to my events list

My friend Georgia came through

With the team assembled, the date was set. I announced it to the list:

Doug would be the star:

That evening, I showed my new friends:

• how to identify muscle mass on their own body

• how to distinguish it from fat (fat doesn’t feel nice to squeeze)

• how experiment with pressure and see what feels nice

• that muscles must be as relaxed as can be to massage comfortably

More on that here:

Then I showed how to use those same intuitions for another creature like Doug:

Doug really liked being massaged.

Chill dude.

He seemed content. I really like Doug.

(By the way, whenever we paused massaging him, he would look at us expectantly until we restarted. I wish I had gotten this on video.)

I saw Doug again a few days ago. He knew what he wanted.

Thanks to Georgia and Doug for existing.

Get invited to my next SF event here.