Solving the Dating Problem Part 3

Tested Keeper.ai, Hinge, Upward, Shuffle, Jigsaw, and Church Swing Dances

In 2024, I wrote Solving the Dating Problem 1 and Part 2. They were among my most-read and liked essays of the year. Since then, I’ve met many women through apps, cold approach, singles events, and swing dances. This is a recap of what worked and what didn’t.

Keeper.ai

Did not work.

Total waste of time and money.

The idea is you sign a contract to pay them a large sum if you end up “marrying” (which means living with) one of their matches. I said what the hell, paid the sign-up fee, and answered 100 open-ended questions. They never sent me a match, and it does not appear they intend to. [I emailed them to see what’s up and they refunded me the signup fee]

Dating Apps

I moved to Greater Boston, a metropolitan magnet for young adults.

I hopped on Hinge and got some matches. Corrinne was a short, brunette, Christian, with a nice smile. We exchanged messages for a few months, and she was keen to meet up.

I once made the mistake of setting up a dinner date as the first date. Just do drinks. I rarely drink alcohol, so I choose a cafe and order tea. If the date was my idea, I pay for the girl.

On the way to Life Alive café, I felt a little nervous. It had been months since I’d done a first date. As the Tesla drove, I pulled up a note on my phone from when I was meeting new women every week in Peru. It said, “Family, recreation, dreams, occupation”. That’s what we talk about. I transmuted any nervousness into excitement.

I got there on time. She was already there. That’s a green flag. She was super nervous and talking at 2x speed. I wasn’t nervous. I paused, looked around and said, “Wow this is a really nice cafe.” She relaxed.

Turns out we are from the same area and went to the same college. She knows people from my hometown. “Do you know Emily B—?” she says.

One of her best friends is a girl I used to hang out with as a teenager. I find this to be hilarious.

We had a similar level of goofiness and conversational skills. We aligned well on religion. The conversation was balanced and enjoyable, intellectual and fun.

We talked and drank tea for an hour.

I walked away feeling good. Glad I went. I followed up, but she did not reply. That’s how it goes sometimes. [Oddly, she replied two months later, “Hey sorry! Took a little break on here! It wrapped up well though”]

After that, I set up a date with another Hinge match, Amanda. I drove to Life Alive again, and within a few minutes, I knew it was not a good match. I got the ick and wanted to leave. But I stayed and kept a cordial conversation going.

After an hour, I said, “I need to leave soon.” She was not responsive to that and just kept talking, interested in learning more about my Tesla. It came out that she listens to NPR and CNN. That’s a dealbreaker.

The café started playing Closing Time.

“I guess it’s time to leave,” I said.

“Why?”

“Because it’s closing.”

I walked back to my car and sat in traffic for another 25 minutes. I resolved not to waste my time like that again. A five-minute zoom call would have been sufficient.

A few days later she messaged me, asking about my Tesla, again. I considered ghosting but instead, I replied, “It was great to meet you, I don’t think we’re a great match”

Upward

A friend recommended Upward, a matchmaking app for Christians. I downloaded it, added some banger photos, and got dozens of “likes”. To accelerate the process, I paid the $20 fee to see the list of women who “liked” my profile.

Here’s the first thing I saw:

The app glitched, making it look like bots. Here are some of other profiles:

The optics are not great. Some of these people, if they are even real people, live hundreds of miles away, despite my filtering for people in my area.

I requested my money back from Apple, and they granted the refund. I selected “Does not work as expected”

Of dozens of profiles, only one person looked promising. She had photos of her hiking, at the beach, and with friends.

Marissa

We “matched” and chatted for a few weeks. I said, What’s your schedule like this week?

Remembering the last dating app date experience. I said, Is a zoom call in the deck of cards?

She said, Yes we can do that!!

I set up a Google calendar event. She showed up twenty minutes late to the call, and said it “Felt so official.”

Perhaps a spontaneous FaceTime would have been more romantic.

She asked me a lot of questions then said, Sorry I’m asking you so many questions.

I love that.

She told me she’s obsessed with bears and visiting national parks. Overall, she was cute and energetic so I said let’s do this in person. We set up an afternoon coffee date at Cafe Nero.

Flip phone photo with Santa

I park my bike and grabbed a table inside the cafe.

“Just parked,” she texts me.

It’s December and a Santa Claus walks in. She comes in behind him. We do a light hug.

A disheveled older man says, “Excuse me can you take our photo?” gesturing toward the Santa.

He hands me a flip phone and smiles with Santa as I click the OK button to snap the worst photo of two people I’ve ever taken in my life.

I hand him the phone and smile at my date.

The homeless-looking man starts blabbering to us incoherently, something about a Santa Claus getting drunk. I nod. He just keeps going. My date is very cute. I’m very uncomfortable. I’m about to punch this guy in the face.

Marissa stands there smiling and looking at the guy, totally relaxed. If she can deal with people like this, that’s a huge plus.

“Yeah okay thank you bye” I say. I turn and order a decaf Americano.

After talking for a while, we walked around the lovely downtown.

She said, “What does your walk with God look like?”

“Wow,” I said, “that’s a big question.”

“It is?”

“Yeah, how bout you go first.”

She told me she likes reading the Old Testament. She asked me when I gave my life to Jesus.

I didn’t have a great answer for that one.

We walked and talked about books we’ve enjoyed and Joe Rogan, whom she’s a fan of.

Afterward, I felt excited to potentially see her again. She was young, based, kind, hardworking, smart, physically fit, cute. It made it easy to overlook the fact that she’s substantially more religious than me, and a little crazy (but aren’t we all).

I followed up with, Hey, I enjoyed our coffee and walk (:

She said, Hey!! Yes so did I! At the moment I don’t think I’m in a good spot to seriously date, thinking of travel nursing and moving around a lot in the near future. But it was great getting to know you and I wish you the best!

This is the adult thing to do. She’s a good person.

I looked at other profiles on Upward. Many of the women said they are looking for a “Christ centered relationship”. I’m sure exactly what that means, but I don’t think that’s what I’m looking for.

My conclusion is that dating apps generally suck. It’s weird to meet a stranger from the internet. It’s silly that this is the mainstream default solution for dating.

Cold Approach: You can just talk to people

I like cold approach. It’s difficult and exhilarating. Many men never even try.

Just now, as I write this, I went up to a random girl at a coffee shop.

We made eye contact, twice. I got off the couch, walked over and stood in front of her.

“Excuse me,” I said. She removed her AirPods.

“I’m writing an article about dating, could I ask you a few questions?”

“Oh, yeah,” she said, “I’m meeting someone soon, but I’m around later…”

“Okay, I’m just wondering, do you think dating apps made the dating scene better or worse.”

“Worse. For sure.”

A nerdy-looking guy walks in, and she stands to greet him.

“Thanks for answering my question.”

I sit down, thrilled. Cold approach is fun.

Georgian Heartbreaker

I was alone at my apartment on Thursday night in December. I hopped on the T and went to a networking event at a popular co-working space next to MIT. I had a feeling I’d meet someone there.

I resolved to talk to the hottest girl in the room. I stood there and looked around. No hot girls.

I saw an attractive girl walking toward the door. She looked at me as she walked out. I decided now is a good time to leave. I exited and she was standing there. I said, “Hey, do you know where an outlet is to charge my phone?”

“Um…” she says.

“Here’s one,” I say, and plug it in.

She’s 5’ 2” olive skinned, dark hair, large brown eyes.

We talk about where we are from—always a great place to start. She says she’s from Georgia, the country.

I pull out obscure knowledge about Georgia.

“The religious leader there offered to personally baptize any couple’s third child in an effort to raise the birth rate, and it worked!”

Her mouth hangs open.

“Yeah,” she says, “People were really excited about that.”

We trade Instagrams. She holds eye contact with me as she walks away.

It felt intense.

The next day I messaged her: “Hi, would you like to meet for a coffee one day next week?”

Eight hours later, I check my Instagram to see if she’s replied. Nothing.

Just then, I got a message:

“Heeey, I am leaving on Tuesday next week. What about next year or between Christmas and New Year?'“

Wow that was uncanny.

After a bit of logistics, we meet for coffee at Life Alive.

She was 15 minutes late.

We sat in the low-light basement of the cafe and talked about our lives, books we like, places we’ve lived, mountains we like to ski.

She asked me about the scar on my neck, which almost nobody ever does. I tell her the story of the accident.

“Let me see it.” I turn my head, and she leans in.

“Did it hurt?” she says.

“My neck was sliced open, so yeah, it hurt.”

We talked and laughed for over an hour. At one point, I became agitated. It felt like she was drilling through the walls I’d spent years strategically building around my heart. I’m a sucker for foreign women.

Eventually we hugged and parted ways.

Over the next few days, I found myself thinking about her, a lot.

I followed up. She replied. I noticed her level of responsiveness was around one text every 24-48 hours. That’s not a good sign.

I said, Did you make a New Year’s resolution?

She said, Happy New Year! No, I don’t do New Year’s resolutions. Do you?

I said, Yes, my resolution is to take you out to dinner

Nothing.

The next day I got a text from Elena. I saw the word “boyfriend” and immediately knew. She has a boyfriend. Of course she does. Goddammit.

That sounds super nice but I thought this might happen. I have a boyfriend and I would be happy to be friends with you if that is smth you are interested in. Sorry if I caused any confusion for you, I just don't want to assume that every guy that approaches me has a romantic interest

I replied, That’s actually awesome. Not everyone is like that.

Intellectually, I’m fine with that. But my heart is crushed.

After that, she started replying to my texts nearly immediately. I decided that just friends would not be feasible. I shared a link to my writing in case she was curious. And that was that.

To this day, my heart is excited by the prospect of talking with her again.

That would be funny if she’s reading this.

A note on infatuation

Some people call it “love at first sight” or “falling in love”. Neil Strauss, legendary writer of The Game and The Truth, coined it “One-itis”. A man’s heart goes crazy, and he becomes convinced. This. Is. The. One.

A gift from god Himself.

She’s. Perfect.

I’ve known her for three hours, but I’m completely sure we’re destined to get married.

There’s typically a degree of physiological illness that accompanies this phenomenon. It can last a week or so. “Lovesick” they call it. Frankly it’s annoying. It becomes hard to think clearly and hard to sleep. When this happens, I tend be more prolific with my creative wok, but often there’s a crash.

Shuffle

At this point, I’m feeling burnt out on dating.

I looked at the relationships around me and decided I don’t even want that right now. I deleted the apps.

Then I got a text from Shuffle Dating.

Three months earlier, a reader said that she went to a Shuffle speed dating event and liked it. It was only $25 so I’d bought a ticket. Now, Shuffle is texting me saying that the event is tomorrow night, and if I don’t go, it’s a $50 no-show fee.

The idea of Shuffle is ten men and ten women go to a well-chosen venue and talk to each other for at around eight minutes each. The host is remote, which I suppose keeps the price low. Participants enter their description into the web app, then the app tells you who to look for next.

Half the women were obvious no’s. Nonetheless, I enjoyed talking to everyone. I was having fun with it.

The app provided cheesy prompts (“What’s your favorite food?”), but I had fun tweaking them (“What’s your take on Trump?”). Most women weren’t my type, but the last one was a gem. We kept talking and didn’t even notice the event had ended.

On our first coffee shop date (not at Life Alive, that place is cursed). I also initiated an important conversation about intentions and timing. What are you looking for? Where are we at in our lives?

I told her the truth: I was burned out on dating, and the reason I went was to write about Shuffle, and to not get charged a $50 no-show fee. I’m not looking to get married anytime soon. I’m planning to travel soon, possibly move, and I’m juggling a bunch of projects.

She was very receptive to that. We’ve been talking and hanging out since.

One thing Shuffle could do is have people enter their basic info and preferences, then organize and invite particular people to events with a high probability of match. Also, they could do less boring prompts and more authentic relating games.

Jigsaw

One of the guys at the Shuffle event said he likes Jigsaw events better, which he said was speed dating while playing ping pong. I like ping pong, so what the hell. I showed up. The vibe was 10 guys per one fat girl while “Buy you a Drank” plays. For a second, I thought it was a gay bar.

Oddly, someone from the internet recognized me. We chatted for a bit, played ping pong, and talked to a few odd-looking women.

I will not be attending another singles event where the organizer doesn’t balance the ratio.

Social Circle

I’m in a large group chat of local young adult Catholics. They put on a lot of events. I went to a swing dance in southern New Hampshire. It was majority single guys, a few couples, and a few single women. I knew most of the people there.

Then I went to a swing dance in near Boston. It was a huge, beautiful venue with 100+ young adults, mostly women. I danced with a dozen of them. One of them asked me a lot of questions, then said, “You’d be a good date for a wedding.” I wasn’t feeling it. She was pretty bad at dancing.

The following weekend I went to a nondenominational church in the same area, just to see what’s up. I sat in the back. Everyone I could see was in between the ages of 20 and 40. In my field of view, I counted 14 women and 3 men. Afterward, three people came up and talked to me.

The hack for meeting good people post-college is finding the right church.

In the past four months, I’ve had three friends start exclusive relationships from friend group connections. I recently went to a brunch hosted by a friend. Both of her roommates were awesome. We hit off. I’m curious to see how our paths align in the future.

It’s great to get to know people in a group setting, see how they interact with others, meet their friends. There’s less ghosting and confusion.

Keep going

Overall, if someone came to me and said, I’m serious about meeting people and finding a partner, I would say

• Live near the people you want to date

• Have friends. Embed yourself in community, church is great for this

• Go to singles events, like Shuffle, that maintain a 50/50 ratio

• Optionally, roll the dice with the most useful matchmaking app in your region and demographic. Make a banger profile and see if you get lucky.

• Learn to dance and go to dances with your demographic. This is so underrated.

If you do these things, you will meet people. If you like someone, open your phone, click Create New Contact, and hand them the phone. Set up a time to get drinks. Being clear about intentions can save everyone time.

The solution to the dating problem is keep going. Try a bunch of stuff. Show up detached from the outcome.

Dating is a roller coaster. Rejection is normal and sucks. Infatuation is real and also sucks. Authenticity wins.

If you simply keep going, keep meeting people, keep learning and developing, good relationships are inevitable.

What is a good life but a series of experiments.

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Thanks for reading, and have a great rest of your day.

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Song

Bonus: The girl at the coffee shop

The girl from earlier is on the couch, writing. I walk over

She looks up. “Are you actually writing an article on dating?” she says

Yeah I am

For…

Do you know Substack?

Yeah, I was wondering if it was Substack. What’s your Substack?

She’s sitting up straight now, facing me, fully engaged.

“Do other people do cold approach or am I the only one?” I ask

Like random people coming up and talking to me?

Yeah

In the context of dating?

Yeah

No, people don’t do that. I have a boyfriend but if I was single I’d love that.

You said dating apps definitely make the dating scene worse. What makes you say that

I feel like they crush your soul. What’s your experience been?

Bad. How do you meet people? How’d you meet your boyfriend?

Through church

She tells me about her non-denominational church. The meeting she just had with her pastor.

She’s a writer. She asks me about monetizing writing. She looks up my book on Amazon.

We talked for half an hour about writing movies. She’s written four screenplays.

“This was inspiring,” she said. “I’m going to write.”