by Niall Doherty

Let me start with this: Your typical guy in the online pick-up community likes to post “field reports,” describing in great detail how he fared while interacting with the opposite sex, rating girls based on their looks, and determining success or failure based on whether or not he got laid.

That’s not what this post is about. I’d rather keep it sleaze-free, and tell you more about what I learned than what I did.

I feel obliged though to give you an idea of how I got on during those two weeks, to at least provide some sort of answer to the question up there in the title. So…

First, a little backstory

I arrived in the Dutch capital on October 14th, one of the first stops on my round the world trip without flying. The plan for my stay in Amsterdam was to work on my flirting skills. I talked all about the motivation for this in a previous post, so go read that if you’re curious. Nutshell version: I don’t like those situations where I see someone attractive and I pass up the opportunity to connect with them because I don’t know what to say, or I don’t have the confidence to approach. That leads to countless little regrets, and I’d rather not sit back and accept them.

So my goal for the two weeks in Amsterdam was to go out and try flirt with at least five attractive women each day. It didn’t matter if I failed miserably. I just had to try.

To help with accountability, I made a deal with my Mastermind group: If I failed to make at least five approaches each day for the duration of those two weeks, I’d have to pay $40 to a charity of their choosing.

Now, $40 is a bit of a sting for me as I continue to work towards generating enough income to cover my expenses (see my latest finance report here). Even if the money would be going to charity, I didn’t want to fail the challenge and have to pay.

But there was also a second part to that deal with my Mastermind group. Because, really, approaching five attractive women a day isn’t that difficult. It takes only five minutes if you’re going for efficiency. But I didn’t just want to go piss off five attractive women each day. I actually wanted to get better at this flirting thing.

So the second part of the deal was that I had to get phone numbers from at least five attractive women over the course of the two weeks.

So, how did I do?

Well, that $40 is still mine. I easily hit my five-a-day target and in doing so I pretty much killed my approach anxiety. I found myself no longer caring what each girl thought of me, no longer trying to make an impression. I was just having fun with each interaction. Lots and lots of fun. As a result, in the final two days alone, I got phone numbers for five girls who I would have considered “out of my league” just two weeks earlier.

I remember one of my first approaches, when I stopped a girl to ask for directions before confessing that I really stopped her because I found her attractive. The words were like tar in my throat; they didn’t feel right and I was visibly uncomfortable saying them. The girl recoiled and quickly moved along. Fast-forward two weeks though and I had no problem getting such words out. They came packaged with a confident smile and strong eye contact, and the response was usually positive.

But enough bragging. I think you get the idea. What I’m saying is that, all in all, I’m well pleased with the progress I made.

Let me jump into a few lessons I’ve learned from all this experience…

The Pain Period

This is big, and it doesn’t just apply to flirting. If you want to become good at pretty much anything that’s far out of your comfort zone, far above your reach right now, you’re going to have to go through the pain period.

The pain period is that initial period of time where you really suck at what you’re doing, and every reptilian instinct is telling you to run away to some place safe and familiar.

“Retreat! Abandon the plan! It’s not worth it!”

Most people don’t live their dreams because they bow out during the pain period. They can’t see beyond it. The short term gratification and relief of quitting is more tempting to them than sticking it out and hopefully reaping the big rewards down the line.

But I have to tell you, as someone who pushes his comfort zone quite a bit and is no stranger to the pain period: Sticking it out is absolutely worth it. Even if you don’t end up getting exactly what you want, just growing familiar with that pain period and learning that you’ve got what it takes to make it through the gauntlet, that’s invaluable.

I went through the pain period in Amsterdam. Big time.

Out of those 100+ approaches, most of them were miserable, ugly, gut-wrenching affairs that I’d rather forget. Some girls shot me down right away. Others looked at me like I was something they’d just scraped from the heels of their new shoes. One night I was getting along great with a girl from Utrecht when a trio of beefy dudes cut in and took over for me. I felt completely powerless. There were nights where I really didn’t want to go out and try flirt, but I made myself do it anyway. I would make myself approach an attractive woman after getting blown out horribly by another just moments before.

Simply put, it was really fucking painful at times.

But you know what? I also had great moments. On four separate occasions I went directly from just meeting a girl to hanging out with her (and usually a friend or two) for a couple of hours. I started getting comfortable telling women that I found them attractive, making physical contact, and asking for numbers. I danced in the street with hot strangers just moments after meeting them. I made genuine connections with some really cool people.

And none of those highs would have been possible without the lows. To experience the payoff, I had to go through that pain period and keep my head held high.

Too many of us are hoping for the payoff without paying the price. We want that girl to like us without having to get rejected by dozens of others in advance. We want to know exactly how to approach a girl first time out, without being willing to screw it up a few times beforehand.

Those rare guys who are willing to endure the pain period? Methinks they’re the ones who win big in the end.

You’ll always have downs

Despite all the progress I made during those two weeks, I found it was still entirely possible for me to have terrible interactions, the kind that left me wondering if I’d actually made any progress at all. For example, my best night out was easily the final night of the experiment. But one of the first girls I approached that night shot me down within a split second. Not only that, but she started screaming for a friend to come over to her so I’d leave. As you can imagine, I felt like a complete asshole and quickly moved away.

But here’s the big difference: Two weeks earlier, such an incident would have ruined my whole night. I would have told myself that I was terrible with women and continued to have ugly interactions for the rest of the evening. But on that night, I found myself laughing off the incident within seconds, regaining my composure, and getting ready to approach someone else.

So here’s the takeaway from that: Even when you do get good at something, you’ll still have your moments of frustration, when you feel like you’re back to square one. But you’ll come to realize that such moments are exceptional. They’re not a reflection of who you truly are and how far you’ve come.


I mentioned my Mastermind group already. If not for the goals I committed to with them, I doubt I would have pushed my edge so much during those two weeks, especially as regards asking for phone numbers. As noted, approaching attractive women is relatively easy. Not so easy to come away with their phone numbers though. That requires building rapport, actually flirting with the girl, showing genuine interest, and getting to a point where it’s not weird for her to give her number to a guy she just met.

And it’s so easy to not ask for that number. I can’t tell you how many times I left an interaction kicking myself because I chickened out and didn’t ask, even when I felt there was strong mutual interest. But with that goal set with my Mastermind group, and with that forfeit waiting if I didn’t deliver, I began forcing myself to ask. I didn’t really have a choice.

And it was hard at first. I sounded awkward and unsure of myself. I asked like I was apologizing, without any expectation of actually getting the girl’s number. But I kept asking. And then I got to the point where the asking became almost effortless, and I found myself with a bunch of new numbers in my phone.

It was only because I had some accountability that I made the extra effort. I knew I had to continuously push my edge, and doing so helped me take some big leaps.

Whatever it is that you’re working on, consider how you might add some accountability to the mix. Make the penalty sting a little bit, so there’s strong motivation for you to put in the extra effort and hit your targets. The consequence of failure shouldn’t just be, “Oh well, I’ll try again tomorrow.” That makes it way too tempting to back off and take it easy.

Get out of your own way

I thought when I got into this experiment that I might have to lie to women to a certain extent. What would they think of me if they knew I was going out trying to chat up women and work on my flirting skills? Well, as it turns out, in the majority of cases, it was no big deal. In fact, introducing that elephant led to some great discussions and deeper connections.

This reinforced my belief that if I’m comfortable addressing a certain topic, other people will generally be comfortable with it as well. The outside world is largely a reflection of how we feel about ourselves. If you’re cool with you, you’ll find that most other people will be, too.

When it came to flirting, I knew that my intentions were honorable. I didn’t have a sleazy agenda, I wasn’t trying to trick girls into sleeping with me. That made it much easier. My values and actions were in alignment. I didn’t have to adopt some fake persona to try impress anybody. I believed that the real me was enough. I just needed to get past the fear and anxiety and allow myself to connect.

My impression is that many guys who get into this pick-up stuff try to break it down to an exact science. They learn off lines and routines and rehearse proven responses to every possible situation they might find themselves in. Now I don’t believe that’s all bad. It helps to have some lines to fall back on when you get stuck for something to say. I personally have a few go-to routines I use when I feel the interaction is stalling a bit, or if I want to break the friendly rapport I’ve fallen into and ramp up the flirting.

I’ve found though that my best interactions usually involve the least amount of rehearsed material. They just flow naturally. There’s me being completely myself, immersed in the moment, not thinking about what to say next, not worried about her body language or where the interaction might lead.

So for any guys out there who might be having trouble connecting with the opposite sex, I’d encourage you to focus less on the external and more on the internal. Become your own best friend. Learn to enjoy your own company and trust yourself in social situations. Because, at the heart of it all, if you don’t believe that you’re a truly attractive person with good intentions, then you’re building on a foundation of rubble.

Going too far

I’ve written about having a fluid self concept before. I’m a big believer in allowing myself to go too far to see how far I can go.

As such, I got overly flirty with several women I approached, came on too strong and lost them immediately. I’m sure that if you folks heard a few of the things I said to girls during those two weeks, you’d probably think I was a sleazy pervert. And hey, maybe I was. But I was willing to play around with that, to don a different hat and see what the results were.

There were other times where I thought I was going too far, only to find that I could still push it further. The line wasn’t where I thought it was.

Consider whatever it is you’re working on. Where can you go overboard? Intentionally push it a little too far and see if that line is where you think it is.

There’s always another chance

Another lesson I drove home to myself with this experiment: You have an unlimited number of chances. If one girl rejects you, no worries, go talk to another. That first girl could have all kinds of shit going on. For all you know, her dad just died or her boyfriend just proposed. There are an endless amount of reasons she might not want to connect with you, and most of them are beyond your control.

Yes, some bad interactions will be your fault. Recognize them, learn from them, and try to do better in future. Forget about the others. Turn right around and go talk to someone else.


If you want to make rapid progress at anything, immerse yourself. It’s painful, sure, just like ripping off a band-aid, but you improve soooo much faster.

I’ve often thought this with Toastmasters. Most clubs in Ireland only meet every two weeks and take a long break for the summer. Back in the Spring I met a guy who’d been in a Cork club for over a year, and he told me he’d completed only two speeches so far.

Two speeches in a year? How much are you really improving at that rate? By the time your next speech comes around, you’ll have forgotten everything you learned from the previous.

I much prefer going the immersion route. Mark off a few weeks or months where you can really dive into something. In the case of Toastmasters, that might mean joining multiple clubs so you can deliver a speech every week. In the case of flirting, it means going out every single day and interacting with attractive women. You build momentum and start to see patterns. It begins to click a lot faster.

Talk to everyone

Whenever I found myself struggling to make my first approach of the day (that was always the toughest one), I’d go and talk to somebody at random, like a group of guys or an elderly couple. I found that it didn’t really matter who I talked to; just interacting with another human being got me into a more social mindset. And that made it easier to then go talk with attractive women.

There were a couple of days where I met up with a friend in Amsterdam and we did the wingman thing. He was a nice guy, but also his own worst enemy in that he wouldn’t approach anyone who wasn’t an exquisitely gorgeous human of the female variety. And then when he did approach someone, he had it built up in his head as a really big deal. He’d just spent forty minutes walking around looking for that perfect girl, and now he had one shot to impress her. As you can imagine, his interactions didn’t go very well.

My advice to him was to be a people person, not just a hot-girl person. Every single person you see represents an opportunity to work on your social skills and develop a more outgoing frame of mind.

(P.S. I first heard this tip from my buddy Teodor, so a shout out to him.)

Know your ultimate goal

My ultimate goal with this flirting experiment wasn’t sex. I’m sure some pick-up gurus would scoff at my “success” over those two weeks. Where I got five phone numbers, they probably would have gotten laid five times. Good for them.

I simply wanted to get better at approaching and connecting with attractive women. Sometimes I found that I really wasn’t attracted to a girl after talking with her for a while. Personality wise, we just didn’t click. And so I’d bow out.

One evening I ended up hanging out with two shy Australian girls. And while I could have pushed it further with the one I found most attractive, I didn’t feel like it would have been a win-win. So I backed off, and focused more on chatting and connecting instead of flirting. It turned out to be one of my favorite interactions of the entire two weeks.

So if you’re a guy interested in doing this sort of thing, ask yourself what your goal is, and stay true to that. If you are just trying to get laid, good for you. But I’d still urge you to be upfront with your intentions and to strive for win-win.

Wrap up

I feel like I’m a different person after my few weeks in Amsterdam, after putting myself through that pain period. I’m now a lot less likely to see an attractive girl some day and pass up the opportunity to connect with her, staying put and cursing myself quietly for not having the confidence, for not knowing how to make that comfortable approach.

Yeah, I considered myself to be a fairly confident and self-assured guy before, but I left Amsterdam having leveled it up a few notches. I pushed my edge, learned a few important lessons, met some great people, and collected no regrets.

That’s living, right there.

UPDATE: I highly-recommended you read this post along the same lines from Karol Gajda: The Game, Sex, Pickup, Social Skydiving, Self-Preservation, Relationships, Ego, and My Weekend In Hollywood


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