by Niall Doherty

This past Saturday in Wimbledon I met up with a guy named Greg. He regularly meets strangers for tea and a chat. We got talking about moments and connections, and how every single person you meet has the potential to change your life.

But most of us are terrified of talking to strangers, scared to open up. And it seems that the bigger the city, the bigger our fears and our walls become. Greg has left all that behind, by putting himself out there online, inviting strangers to meet for tea, having deep and meaningful conversations. He’s being the change he wants to see in the world.

One thing Greg said stuck with me.

I was telling him how I believed the whole “don’t talk to strangers” thing is good when you’re a kid, because it prevents weak and defenseless you from being taken advantage of. But Greg disagreed. His argument was that we should be teaching kids to talk to strangers effectively, helping them develop skills so they can judge for themselves who’s trustworthy and who’s not.

I like that idea. The ability to strike up a comfortable conversation with a stranger is a valuable skill, and one that the vast majority of us never work on. I believe that a few simple words, a brief and fleeting interaction, has the potential to change lives. In fact, many of us probably wouldn’t exist if not for people talking to strangers, as that’s likely how your parents or grandparents met, directly or indirectly, through someone taking a chance and extending that olive branch.

Working on it

This year, I’ve been consciously working at talking to strangers. As I’ve written about before, I used to be incredibly shy. I’ve overcome that to a large extent, able to talk to pretty much anyone about pretty much anything in social situations. But striking up a conversation with a stranger is another level altogether. That means spotting someone interesting, approaching them, and entering into easy conversation, without coming across like you have an agenda. It’s about building fast rapport and letting the other person know that you’re cool and trustworthy.

Getting better at this is all about practice. I try to talk to everybody. Young, old, black, white, doesn’t matter. This past weekend in London I must have struck up conversation with at least a dozen strangers. The beefy guy waiting outside the sushi place, the Indian lady at the smoothie stand, the three English girls on the train back from Wimbledon, the very angry man who didn’t like being asked for directions, two German girls outside a pub, several people at my hostel.

Sometimes I do well, sometimes I don’t. But I keep on trying. And I’ve gotten a lot better.


This is a part of talking to strangers that I’m particularly interested in. For a long time I was the kind of guy who would see an attractive girl and not go talk to her. I didn’t have the skills or the confidence that I could strike up a comfortable conversation and give myself a solid chance to connect.

This has led to countless little regrets over the years.

Because every time you see someone attractive and decide not to go talk to them, you’re passing up what could be a great opportunity for you both, perhaps even the opportunity of a lifetime. For all you know, you could be a perfect match, but because you get scared and don’t know what to say or do to initiate conversation, the opportunity is lost and you’re left wondering what if.

After working consistently at talking to strangers for the past year, and regularly approaching girls I find attractive, I’ve gotten a lot better at it. I can now initiate conversation quite comfortably with most people, and I’m nowhere near as intimidated by physical beauty as I once was. The key for me has been to keep my mood light and playful, and not ask too many questions.

But I’m still at a sticking point with flirting. That’s something which doesn’t come at all naturally to me. I struggle to cross that line from friendly to flirty. Historically, a girl would have to make it very clear to me that she was interested before I’d make a move on her. I’ve never considered myself very assertive when it comes to making that move, and it’s something I’m working on.


There is an ever-growing “pick-up” community online, and books like The Game have inspired many young men to get out there and start talking to real women.

There is a sleazy side to it all, and I expect that, no matter what I write here, some people will paint me with the sleaze brush if I’m out and about trying to talk to girls. But for me, the key is in the intention. And my intention isn’t to sleep with as many girls as possible. I’m pretty open sexually and I’m not opposed to one night stands, but that’s not my motivation for experimenting with all this.

This is more about working on myself, another area of growth. Again, I don’t ever want to be in that situation where I see someone attractive and I pass up the opportunity to go talk to them because I don’t know what to say, or I don’t have the confidence to approach. I want to get to the point where I can easily go strike up a conversation with a woman without coming across any way creepy, build rapport and give the both of us a chance to see if we’re compatible, if we can have fun together and leave each other better off than before. Win-win, that’s my intention.

Instead of pick-up, I prefer to think of it as connection. I’m not trying to pick someone up. I’m trying to see if there’s the potential for deeper connection. I’m not trying to trick anyone. I’m not a big fan of pick up lines or acting completely different from how I normally would just to impress a girl.

This is about becoming a better, more attractive, more opportunistic version of myself.

The plan for Amsterdam

I have a few more days left in England, and should be in Amsterdam by the end of the week. I intend to stay there for a fortnight, hopefully get set up with an apartment. Methinks that will be the perfect city to work on my flirting skills, as I’ll be able to go out there pretty much every night. The goal will be to approach at least five attractive women (or groups of attractive women) each night, try to build some rapport and be flirtatious.

I’ll avoid approaching women standing in windows or on street corners 😉

I’m willing to make mistakes and go a little too far with this to see how far I can go. It’s all about pushing my comfort zone and seeing what works. Remember, I believe in a fluid self-concept. “I’m just not a flirtatious person,” is a lame excuse in my book. I believe I can get good at flirting if I just work at it, and these two weeks in Amsterdam will be a good test for me.

Why I’m telling you this

Part of it is accountability (announcing my goals publicly has always worked well for me). But a bigger part is that I know there are some people reading this who know exactly what I mean when I mention “those countless little regrets.”

For too long I was the kind of guy who never really ended up with the girl he was most attracted to. I just didn’t know how to make that happen. But now I know that I can become that guy (I’ve already made made huge strides this year). And I want to put this out there for anyone else who is like that younger version of me. I don’t want you to pass up those opportunities either. I want you to be able to go talk to that hot girl in the park and come away with a date for the weekend.

And for the ladies reading this, I’d encourage you not to settle either. The same principle applies: If you see a guy you like, you should be able to go talk to him and give yourself a good chance to connect. You never know, he could be the love of your life, or just a good dude you have some really great sex with before going your separate ways.


I’ll leave you with a few bits and pieces I’ve come across online that I’ve found helpful…

  1. Tynan was one of the guys featured in The Game, and I find his philosophy on this stuff fits well with my own. You can read all about how he became a famous pickup artist starting here.
  2. Matt Ramos over at 30vanquish is on a mission to break free from social anxiety and regularly writes about his experiments striking up conversations with strangers, many of them of the attractive variety.
  3. This is a lengthy video (almost two hours) of a chap named DJ Fuji, speaking all about “the core fundamentals of game.” I like him because he goes way beyond the shallow and gives advice on becoming a more attractive person, not just faking it to get your rocks off.
  4. Finally, check out this channel over at YouTube. I like these guys because they demonstrate how much easier it is to connect with people when you go in with a playful attitude and forget about trying to impress them.

Your thoughts

I expect this post will get a mixed reaction, and I’ll probably lose a few readers. I’m cool with that. Let me know your thoughts in the comments, and feel free to share any other non-sleazy resources that you’ve found helpful.