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  • Writer's pictureDillan Taylor

This flirting advice changed my life


An actual fake photo of me flirting with women.

I enjoy talking to strangers out and about. I learn their names and even their stories if I can.



Two weekends ago at a Miami bachelor party, I took a morning stroll on the beach. This guy saw me stretching and asked if I spoke Spanish.


"Solo un poco," I said. "Que tal?"


He told me he ran a martial arts gym in Barcelona and he was on vacation with his dad. Then he asked if I could take a video of him shadowboxing.



After doing so, we chatted for a few minutes. I stumbled through with my four-year-old level Spanish but I survived. We discussed jujitsu, Spain, and the rest of his American road trip. We exchanged WhatsApps and followed each other on Instagram.


I'll likely never see him again but it was a lovely start to the day.


 

A few days ago, I did some late-night climbing at my local rock climbing gym. I forgot my headphones but felt grateful because I thought it would make me more approachable.


I find climbing to be a cheat code for meeting people. You're constantly in close proximity to other people. You can ask climbers for help with the route you're stuck on. It's also a wildly supportive culture in casual gyms.


I was struggling with this route, so I asked the dude next to me (who was clearly better than me) for his input.


He tried it next and even he had trouble. I felt vindicated.


We talked through it together and naturally started chatting it up. We exchanged names and numbers, bumped fists, and climbed together until the gym closed.


It turns out he loves to play chess as much as I do. We're playing at his place this Sunday.


 

Patagonia, 2023.

I met a Brazilian woman while living in Buenos Aires. She's visiting the United States for the first time in a few days. And when she's done traveling around Europe in October, we'll meet up again in South America and backpack our way down to Argentina.


We met at my coworking space eight minutes from my BA apartment. It was during our Tuesday "Coffee & Cake." Nomads would take a break from work to connect with each other while downing sugar and caffeine.


When she walked up to grab some cake, I gently smacked her hand and said, "Oh actually, they explicitly said you were not allowed to eat any of this cake."


Dillan you smooth devil.


Without skipping a beat, she looked over her shoulder, took a bite of cake, and replied, "Could you do me a favor please and not tell anyone I had some?"


We laughed and started to get to know each other. Work got neglected for the next few hours because we just kept talking.


From that afternoon until the day I left Argentina, we spent practically every day together.


 

So what's the point of all these stories? It sounds like I'm just bragging about how extroverted and gregarious I am.


My point is that building the habit of connecting with strangers has easily been one of the most rewarding aspects of my life.


And it all came from a three-minute clip.


Craig Ferguson was the host of The Late Late Show. He was known for his avant-garde talk show style. His interviews weren't scripted and he would show zero care for a person's celebrity status. Above all, he's famous for his ability to successfully flirt with the world's most beautiful actresses and stars. Never creepy. Always cool and silly. (There are numerous compilation videos of him doing this.)


In the short Tiger Belly clip, they ask Craig for advice to young men who are scared to talk to women.


"Here's what makes me very cool," he begins tongue-in-cheek. "I'll talk to you, no matter who you are...the same way. If you're Desmond Tutu, Kurt Russell, or a gardener fixing the fountain...You will get the same respect from me. Because you're a human being."


Since hearing that years ago, I've done my best to embody his words in my own way. The repackaged advice I tell people is:


Flirt with everybody.


I'm not the most charismatic or desirable man on the planet. But I'm quite calm and confident when talking to beautiful women.


Not because I've mastered the art of seduction. But because I flirt with everybody.


Old men in the grocery store. Bros at the gym. Couples walking on the sidewalk.


I tell jokes, ask questions, and try to connect with just about anyone I bump into. Sometimes it's just a sentence or two. Sometimes it's a new chess buddy. Sometimes it's an international girlfriend you make future plans with.


 

Not everybody is comfortable in their own skin while talking to strangers. I used to be that way.


I would run errands or go to the gym feeling like I was in the cockpit of my own head. It would've been the end of the world if someone randomly started talking to me. I feared stuttering over my words, looking like a creep, and doing anything remotely embarrassing.


But over time, I just practiced flirting with people. Not romantically. Just getting my reps in when it came to human connection.


It gets way easier.


Plus, if you flirt with everybody, then flirting with one specific person becomes lower stakes. There's nothing riding on the success of that moment because this is what you do to everyone all the time.


It's like a bar that cards everyone who orders a drink, no matter their obvious age. That way, they never have to worry about serving someone underage.


How often do you talk to strangers?


The next time you're out, try to spark a few conversations. One or two sentences minimum. See what happens.


 

PS—My friend at AchieveYou made a cool Instagram reel about loneliness.


I'm in it. Check it out!

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