I’m looking for single women who are physically and mentally healthy, read books, and do activities and projects. 100 years ago, that was most Americans. Today it’s a small minority.
Part 1 of Solving the Dating Problem got 37 comments. I articulated a few factors making finding a partner more difficult: sparse IRL networks, dating apps, hypergamy, and chronic illness.
The above generations don’t have much advice. “Try the apps” is the cultural default.
Most of the new relationships are forming from online or social circle. Less common avenues are matchmakers and singles events. I talked with Wes from Keeper.ai, a matchmaking startup who gets paid when the a client gets married to their match.
Wes said,
Basically we've got about 270,000 people in the pool right now. We get a few thousand people per week.
What the AI basically does is take it from 100,000 potential matches down to less than 100. Then the human matchmakers take over.
Last week, we had two new engagements and our first baby, which is exciting.
If we send you on a first date, it’s looking like a one in six chance you get married.
What would you say are like the primary determinants of success here for a relationship?
No single thing determines it, and it can be different because people give different things different importance.
One person might be they just need someone they're very physically attracted to, and that's sufficient. But then the bar is higher there for what is physically attractive.
For other people, there are certain assumptions about intelligence. You need to be relatively close in intelligence. Ideally, the man should be a little smarter than the woman. Obviously, smart is a very nebulous term. She'll have strengths where you have weaknesses and vice versa. But if you wanna reduce it to a single number, you would want the man to have slightly higher IQ.
The openness trait on the big five is very important. All the big five traits are important.
The openness trait is your propensity for creative thought and abstract thinking and wanting to discuss new ideas and things.
Someone who's a substack writer who likes exploring different ideas, you can't match him with a girl who just wants to watch reality TV.
True.
Shared values is a big one.
We need you to be able to hit it off in the short term. You have things to talk about. You like doing the same things. You're attracted to each other. But then in the long term, there's gonna be a point in the relationship where you get down to brass tacks, and it's like, what does this future look like here? Do we want the same things out of life?
Do we want to have the same structured family? Do we want the relationship dynamic, the masculine, feminine, what have you, to be the same between us? That's very important. And those are things you're not gonna discover about someone usually in the first couple months after you meet them.
My most recent relationship fell apart because of stuff like that. And I didn't meet her through Keeper, which is probably part of the problem.
If I ask you how you wanna raise your kids, that's gonna tell me a lot about how you approach life and what the future holds. If you guys align fairly well on that, and you align on politics and religion. Those things serve as proxies for what are deep seated alignments that are gonna predict success.
Where are you finding the women?
All over the place. Social media is big. Word of mouth. We get alot through Google. And through tools we built on the website. We have this thing, Standards Calculator. That thing went mega viral and we got a ton of women from that.
It calculates the percent of the population that meet your standards.
I made friends with Simone Collins through podcasting. She co-hosts Based Camp pod. I visited her in Pennsylvania where she has four children. It’s exceedingly rare for a non-Amish woman to bear four children. She and her husband Malcolm wrote Pragmatists Guide to Relationships. I messaged her that I’m trying Keeper.
Simone wrote back,
Honestly you're doing the right thing: Trying a lot of different channels and considering this as one (of many) potential pathways. The only bad thing would be to just "hope the right person comes along" or get passive (e.g. sign up for this and then NOT also personally get on dating apps, aim for at least three dates with new people per week (ideally five or more), etc.
I replied: Ha! 3-5 a year would be good in New Hampshire. I did 3-5 a week in Peru. It was only possible because I would get dozens of matches every week.
If you're serious about finding a wife, it sounds like you'll need to leave New Hampshire. ^_^
Yup. Today I was touring places in Cambridge and Somerville.
That's wonderful! Really glad you're doing that. Those are GREAT places to be networking in a search for a life partner.
[In regard to Keeper.ai] I would definitely see $1XK as a worthwhile success fee for finding a wife.
Wes, from Keeper, sent over the marriage bounty contract. The word “marriage” means something different than I thought.
Chris and a Match shall be considered to have entered a “Marriage” if any of the following apply.
enter into any legal marriage, as certified by a Notary Public, by self-solemnization, or as recognized by a local, state, or federal jurisdiction.
have been in a romantic relationship for at least 18 months.
have been living together for at least 12 continuous months (including any period in which Client and Match were separated for less than 90 days).
Match becomes the parent of Chris’s child by birth or adoption.
Chris becomes the parent of Match's child by birth or adoption.
Chris and Match hold themselves out to their family, friends, and/or community as married.
Upon entering into a Marriage with a Match, Chris shall pay Keeper a sum of $1X,000 within 14 days. If Chris should delay in payment, Chris will be responsible for collection costs, including an interest fee of 5% per month, compounded monthly, in accordance with the applicable laws of New York State.
5% interest per month is aggressive. Overall, it seems reasonable. In three clicks, I signed and paid the $250 signup fee.
Economically speaking, it makes a lot of sense to partner up. For example, I have the cash for a down payment on a house, but I don’t have the W-2 income to get a mortgage. If my partner has the income and I have the down payment, now we can buy a property. Or we can share a rental.
Partners can split up life duties like shopping, cooking, and cleaning. It makes sense to partner with someone who you can work with. After all, you’ll be spending your life together. To me, to be able to work on projects together is of high importance.
A woman commented on part 1 that “fun” is the first thing she’s looking for in a relationship. I think some amount of fun is important, but as Louise Perry points out, the primary benefits of a long term relationship like marriage has historically been economic and reproductive. There’s a difference between dating for “fun” and dating for marriage.
I’d give Keeper.ai only a 15% chance of success getting me “married”. But when something is important enough, you do it even if the probable outcome is failure.
After I signed the contract, I got an email from Amanda, senior matchmaker at Keeper.
Required Action Items for You:
Finish uploading photos
Additional Information
Our AI algorithms and human matchmakers will get to work analyzing thousands of possible matches for you.
I answered 80 questions and shared photos with them. The ball is in their court. But also, it’s still in mine.
I asked Amanda about advice for photos. She recommends professional candid photos. She said,
“Consider hiring a professional photographer. Few things will increase your results faster.”
“Smile, be casual, avoid awkward/forced poses”
“Dress in a variety of ways, intentionally and sharply.”
“Avoid group shots.”
“Here is a link to a blog Wes wrote on taking strong photos”
The key paragraph:
The need for good photos goes deeper than physical attraction, because photos communicate a lot more than just what you look like. When a woman sees your photos, she’s going to make a broad range of assumptions about you: What’s he like to be around? Is he fun? Is he confident? Does he have friends? Is he interesting? And, most importantly: Can I see myself with this man?
At the end of the blog Wes recommends working with The Match Artist to get great photos. I booked a call and got a 30 minute sales pitch. The guy said,
If she doesn’t view your character as a happy health smart guy, you’re done. She’s gonna judge your body language and expressions. She’s gonna decide if she thinks you’re a healthy happy person based on how photogenic you are. That’s what’s gonna happen. You only need one photo that’s slightly less photogenic than the others for her to be doubtful, and then you’re probably done. I need your photos to be consistent with healthy happy smart, and feel candid.
He talked for 25 minutes straight and quoted me $2,699 for a five hour photo shoot.
I didn’t do it.
A local experienced photographer is $349 for a 1 hour shoot. I didn’t do that either. I can do it myself. It did not occur to me to take photos with the specific intention of creating a dating profile.
Pro tip: Do more than vacation photos from five years ago.
My father is 70 and is dating via Match.com. He said he went on eight dates and only liked one person. He says that every person he talks to on the app comments on the photos he put of his sculptures.
Photos of your work is low key genius. I might add a photo of my artwork, and a screenshot of my Substack.
The Hinge Game
Step 1 is to live in a place where the target partner demographic lives. In Boston, 35% of the population is between 20–34 years old. That’s much different than where I used to live, in New Hampshire, which is the second-oldest state in the country. Still an awesome place to live, but not for dating for young people.
We need options and we need to meet them. Hinge is really the only viable dating app for my demographic. I dusted off the smartphone cobwebs, opened the app, changed my location to Boston, my new home city. I matched with a few women, one of whom asked me to meet for a drink. Great. Another, a Russian-American gymnast, had a compelling set of photos of her doing activities and no photos glorifying drinking alcohol. Great.
I messaged the gymnast, Hey, good morning (:
She unmatched with me. lol
I don’t overanalyze these things.
Online is a numbers game to find a good match. You don’t really know if it’s good until you meet IRL. It’s useful to have a tried and true introductory process, with good messages and a meetup spot. In South America, it was very simple.
I would say, Hola linda, which roughly translates to Hey pretty girl.
She replies.
I say, Puedes hablar en ingles?
Mas o menos
Esta bien, siempre seducirte con mi gringo espanol
Jajaja, que lindo
Do you want to meet for a drink or a dessert?
She says yes, then we switch to WhatsApp and do logistics. It works very well (minus South American stomach problems.)
We meet up for a drink or dessert, then decide if we want to meet again for dinner. In South America the man always pays for everything.
In America, I’m developing my intro process. It’s unclear what the cultural norms are. I don’t think everyone is on the same page, which can make for uncomfortable situations. Right now that’s just part of the game.
If you use the apps, especially as a man, there will be some amount of “ghosting”. Doesn’t do to dwell on it. Remember, women are getting 10X more likes, 10X more matches and 100X more messages. It’s a bottomless well of digital men lusting after them. It’s far from the ideal mating environment for both of the sexes.
My brief browsing of Hinge Boston and friend anecdotes indicate that it’s worth it to update my photos to photographer-grade and try a month of Hinge membership for $50. Both men and women often hesitate to spend money on partner-finding. But if you’re going to play, play to win.
I suggest trying a dating app memberships if:
your digital profile represents you well
you are in an area with people in your target demographic using that service
you have an introductory process including messages and a meetup place
you are okay with getting ghosted by 30-50% of the people you message
Dating apps are one of many partner finding strategies and it would be foolish not to try. Even if the chance of success is only 10%, it’s worth rolling the dice with good photos and a paid membership.
In part 1 I introduced my childhood friend who is a solid 9 working in Hollywood and dating around in LA. He told me,
Two nights ago, I was out and got a phone call from a girl who ghosted me. She never texted after we met up three times. I thought either she didn’t see the message, and that’s okay I don’t care, or she ghosted me, in which case I don’t want to follow up
She called me and said, I’m so sorry, I thought you ghosted me because I didn’t see the message. I said I’m seeing someone now.
I think it’s better for this girl. We would’ve hooked up the next time I saw her. But I wasn’t gonna date her. And now I’m seeing someone I like. So it’s definitely better for me.
I had a girl over, we were making out, it felt safe to ask if she wanted to go back to the bedroom. She said yes, then said, no I don’t want to do that right now, I’m trying to be better.
Like she’s having sex too frequently.
Then she’s like, uh, you’re making it really hard not to.
Honestly, that bothered me. She’s trying to convince me to convince her to change her mind. That’s too many layers of responsibility being put on me.
I said to her, and it’s kind of a dick thing to say, I said:
I am confident I could change your mind, but I’m not going to because you communicated a boundary to me and I don’t want either of us regretting it.
She said, Okay I don’t want to now, but next time I will.
I don’t relate to that. That’s the girl that called me two nights ago.
The beginning is, I met her on hinge. I hadn’t responded to her message. After 48 hrs and she texts me, “I thought there was something here. L.”
She thought I was ghosting her after 48 hrs. We hadn’t even met yet. I was busy. Someone ran into my car at work.
I’m like, okay, this girl is a little much. I thought, ah screw it, I met her, and I brought it up.
“I’m afraid of being ghosted,” she said.
I said, Can I give you advice? Don’t do that. I almost didn’t meet you, but I’m glad I did because I’m enjoying our time together.
When you don’t have the phone number, just hinge messaging, you get ghosted so much. When you get more messages, you get more comfortable, you have more options, you start ghosting.
The hinge culture is you don’t invest emotionally until you meet in-person.
You get less emotionally invested after getting ghosted a few times. You get a match with a girl whose super hot, and you get excited, then you remember she’s prob not gonna respond after the second message and that’s okay.
As you get more and more [date opportunities], you’ll need more criteria checked off to go and meet them.
It's worth it to invest [in photos and prompts], but it's scary and annoying.
One person stuck out of fifteen dates in the last year.
I have a Hinge date lined up for next week.
I’m learning that there are many things we can do to increase our chances of meeting a good match.
Solving the dating problem is doable.
I will check out singles events, go on more Hinge dates, update my photos (again), continue working with Keeper, and report back in Part 3.
Thanks for reading, and have a great rest of your day.
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Bonus: Amish vs College
Last fall I stayed with an Amish family near Lancaster, PA for three days. I made friends with Steven, an Amish father of four and serial entrepreneur.
I look to the Amish to see what has been lost. They seem to be more advanced as they have taken fewer steps backwards implementing “disruptive” technologies.
Steven has a flip phone that he leaves at his house for emergencies. I called him to talk about dating. He didn’t answer, of course, so I left a message and five days later he called me back.
He said that typically Amish people find their spouse in their youth groups and there are 40+ groups in the Lancaster area with 30-100 young people in them.
Typically every Sunday we get together, and on weekdays we get together in smaller groups, either sing for some elderly or just get together and play volleyball or sports or whatever. Typically that's a smaller group that would be within the larger group, but the larger group would get together every Sunday, sing and have dinner
You meet hundreds of people, and you get to know about that many as well. It's not really narrow as far as your options.
There’s a lot of young people, half of the population is under 18.
“Ghosting” isn’t possible when everything is IRL.
Steven said people typically get to know each other they even start dating. They date for around 6 months to 2 years before getting engaged.
The Amish youth groups reminds me a bit of college, but with less binge-drinking and more singing for the elderly.
None of my friends met their partner in college. The college campus is remarkably bad at partnering couples for long term relationships. College is a transient experience. People are coming from all over the place, transferring in and out, going away for summer and winter breaks, studying abroad, and moving away upon graduation.
I talked with Jaime, a 21-year-old writer and artist who made the drawings in part 1.
“College is such a unique environment where people can meet organically,” she said.
I asked her about the dating apps. “Most people are on it for attention or validation, or if they’re bored. It’s really addictive. It hooks into the most primal part of your brain. It’s addictive to scroll past people.”
“Once you graduate college, the social scene changes dramatically,” I said. “It goes from a room full of people your age, to you being the youngest person in the room by a lot. My advice to college students is to meet as many people as you can and forge relationships that go beyond graduation. Make the most of that environment.”
Thanks, again, for reading.
Photos
“do the same thing but a girl”
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The best way to solve the dating problem would be to eliminate dating.
I just want to be a housewife and live out in the country, but I feel like the kind of guy I want isn't on dating apps. I'm tempted to go volunteer at a ranch or something.