What Happens When You Try Flirt With 100+ Women In 2 Weeks In Amsterdam?

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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  1. Hey, Niall.

    Glad to hear you’re having fun in Amsterdam. Fun city. I wish I had had more than several hours to explore it. I ran out of time without seeing much. Can’t say I flirted with anyone while I was there, either. Any idea how much longer you’re staying there? Just curious; I know you don’t plan to rush your trip.

  2. Nice one, Niall! When you can show up as who you are and let women know that they are beautiful beyond their physical appearances, that’s a gift they can’t refuse, though they may not accept it. I’m sure you’ll start giving more of it…

    By the way, when you’ve made connections and you lead them (not manipulate them, but lead), all you need to say is something along the line of “I want to see you again” rather than “Can I get your phone number?” It’s an open invitation for an adventure 🙂

    1. Thanks, Masa! And yeah, that’s a much better way to say it. I actually said something similar, like, “I like you, we should definitely hang out some time. Let me get your number.”

      One girl called me on that: “Wow, that’s not even a question, you’re just assuming I’ll give it to you.”

      But hey, she still gave me her number 🙂

  3. Awesome post, Niall. This is truly what life’s all about. Finding out what you want to get better at and totally immersing yourself in it. I enjoyed the longer post, thanks!

  4. I love love love love love Amsterdam. (Have I told you this frequently enough yet?) And I love (x4) the lessons you got from this experiment. This is hugely inspiring. Good stuff, Niall! Thanks for sharing.

  5. Hey Niall, interesting post with a number of ‘on the money’ lessons. The One I’d like to return to is the ‘paying the price’ one. This has been a favourite of mine since I saw Billie Jean King interviewed with Martina Navratalove a few years ago. Billie Jean Mentored Martina on her rise to the tip top of the world rankings; a place she stayed for over ten years. Billie Jean was so passionate about the fact that EVERYONE HAS TO PAY A PRICE FOR SUCCESS. But more importantly she made the following point. You don’t know where it will take you, you just have to pay the price.

    In Martina’s case it was sacrificing seeing her family (she left the eastern block to pursue her tennis career in the USA), deciding to buy into new techniques like visualization and positive thinking (I know!) and committing totally to her practice and fitness schedules. But Martina didn’t know this would make her number one in the world for ten years. It might only have taken her to number ten! But SHE WANTED – AND WAS PREPARED – TO FIND OUT HOW FAR HER TALENT WOULD TAKE HER! In other words she gave herself the best possible chance.

    That’s the lesson. Commit (or immerse as you say in this post), stay on track and the results will be what they will be. But even if you don’t get to the very top, man will you learn a lot about yourself – a point borne out in spades in this post!

    Stay cool dude, ice cool if you can.


    1. Love that, Stan. I agree completely. We just have to set the wheels in motion and appreciate wherever we end up. For me, the biggest reward is knowing that I gave it my best shot. Doesn’t really matter if I have the external rewards to show for my efforts.

  6. Well done Niall

    Now you’ve had your warm up in approaching.Did you do days and nights?

    When you get to Munich you can step it up a notch with the Bavarian Beauties and see how they take to the Blarney 🙂

    Maybe das Frauleins will be more accomodating.

    Hope you’re enjoying Germany,a bit of an overlooked country for travelling I think.

    1. Thanks, Aleks. Agreed about Germany. I’m liking it a lot so far, pleasantly surprised.

      And yes, I went out both days and nights in Amsterdam, mixed it up a bit to see which was easier. I came to believe that night time was better. The girls I approached then were almost expecting to be hit on, so they were more tolerant of my antics 🙂

  7. Brilliant stuff, Niall!

    After playing around with various ways of approaching women myself about two years back, I finally realized that I much prefer meeting people through mutual interests than randomly on the street or in a pub. And no, it’s not just because approaching out of the blue is scary as hell. 😉

    That being said, maybe a bit more practice of starting conversations with random strangers in random situations could make life a bit more fun sometimes. Hmmmm…

    1. That’s a really good point, Vlad. Some of my easiest approaches came at meetings of some kind. For example, one day I went to an Expat fair, and striking up conversations there was just so much easier, because me and the girl would have something in common to talk about right away. Really helped get the conversation flowing.

  8. “Sleaze-free”? SLEAZE-FREE?! Dammit man, I came here for the sleaze!

    Seriously though, this reminds me of that old joke. A man asks his friend why he’s so successful with women, even though by most standards, he’s not the best looking guy.

    “Simple,” the guy replies. “I go up to them and ask them if they want to f__k.”

    “Damn,” his friend says. “You must get a lot slaps.”

    “Sure,” the man responds. “But I get an awful lot of f__ks too.”

    [Excuse the language!]

    On a wider note, it’s this kind of confidence that allows us not only to approach attractive women, but ask the boss for a raise, ace the interview, or speak in public. Once we’ve gone through the pain period, anything is possible because we’ve overcome that illusory fear of other people’s judgement that held us back.

    Not that I’m going to try this exercise, though. I don’t think the wife would approve.

    1. Thanks Cliff. Language excused. You didn’t even need to go to the trouble of censoring 🙂

      That old joke reminds me of a story an elderly Toastmaster friend of mine used to tell. He got the hottest girl in town to go to the prom with him, and all the jocks were stunned. They asked him how he did it, and he replied, “I just went up and asked her. Everybody else was too scared.”

      He ended up marrying that girl, too!

      And yeah, great point about how conquering the pain period in one area gives you confidence in others. Once you know you can beat it, anything seems possible 🙂

  9. Niall

    I absolutely loved this post! Awesome! So glad you learned so much from your experiment and had fun along the way. Oh ya…bravo on keeping your 40 bucks! Lots of good stuff here that I really enjoyed. Keep doing what you’re doing and take care. 🙂

  10. I was so looking forward to this post. Of course it didn’t disappoint. Thus why my comment is so long. 🙂

    Loved you talking about the pain period in your video. It’s so important to acknowledge there’s no way around it. I went to a networking event last night and I almost turned around after I arrived at the location because I didn’t want to go through the pain period of entering a room full of strangers by myself (it’s one of my struggles) but I had a short conversation with myself and walked towards the pain. ha ha. Of course it ended up being a great experience.

    Now I’m going to apply this to flirting like you did because I am horrific when it comes to even making eye contact with attractive guys. Hmm maybe I need to make this my goal in our next mastermind meeting. That accountability thing is really working for us isn’t it. 😉

    Love this quote:

    “If you’re cool with you, you’ll find that most other people will be, too.”

    I have a question…

    Do you think pushing yourself outside your comfort zone is like a muscle? Meaning you need to keep exercising it in order to stay past the pain period? I wonder if you stopped approaching attractive women for say a year, and then started again, if it would come back like riding a bike or if you’d have to go through that pain period again. Just curious.

    Thanks for so many great lessons in this post.

    1. Thanks, Kai!

      I actually took a week-long break from approaching attractive women after the experiment, and then on Saturday night I made a few approaches again in Frankfurt. It was definitely tough to get back into the swing of it. All the momentum I had built up was pretty much gone. And I see that Tynan recently started getting back into pick-up again. He was one of the guys featured in The Game, so he was really good at one time, but after a while, once he’d stopped practicing consistently, he noticed that he was having trouble making approaches again. So he jumped back into it full time.

      That said, I believe if you make it through the pain period once and get good at something, it’s easier the second time. Like learning languages. They say your first second language is always the hardest, but once you get good, you’ve conquered those limiting beliefs that said you couldn’t do it, proved them wrong.

      P.S. Would love to read about your experience if you do your own flirting experiment 🙂

  11. Niall,

    So glad that you’re getting along well on your round-the-world trip thus far. I keep reading your updates and rooting for you, and just wanted to say that this latest lengthy post is one of my favorites. I can remember wayyy back in high school when a friend of my younger brother was hanging out, saying something to the effect of “You just gotta go DO IT!” I don’t know where his confidence and early wisdom came from, but I took the very simple advice and, like taking that dive off of a high cliff into some gorgeous blue water, I called up the girl I’d been crushing on forever and asked her out to coffee. And she said yes. She’s happily married to someone else these days, but that experience has stayed with me through the years and reminds me of the same attitude you’re taking in your experimental life – stop thinking and worrying so much, and just DO. We’ll always regret the things we didn’t do more than the things we did, because at least action leading to a setback doesn’t leave room for “what ifs.” Keep it up!

  12. Aleksey Vitebskiy

    Awesome story Nial. One comment I want to make is that I think you strove a little too far into the noble cause thatbis your flirting experience. Getting laid is not a bad outcome of a social interaction. I completely support you quest to become a more sociable person, but don’t rule out a possibility of a a couple of random encounters, or maybe even a relationship. Casual sex can be fun, especially if all the parties involved are having fun. I think you have a slightly patronizing attitude towards women. There are plenty of girls that want a random sexual encounter every once in a while. Heck, I’ve seen plenty of one-night stands turn into lasting marriages, and I’ve seen them turn into a buddy-buddy type relationshipsas well. Keep your mind open at all times. Be observant,but don’t oberthink

    1. Hey Aleksey, thanks for the comment. Don’t worry, I’m not ruling out such encounters. As I mentioned in the previous post about flirting, I’m not opposed to one night stands, or longer term relationships. As long as it’s win-win, it’s all good.

      I just won’t be spilling the beans on such encounters here on the blog, that’s all.

  13. Hi Niall,

    I have been reading your blog for about 8 months now and really enjoy it! I even forward some of them to my young adult daughter for inspiration, as she has the travel bug as well and I find a lot of your posts very motivating, as a person growing through life, not just going through life.

    I wanted to post on this topic because it hit home with me. I am just starting to launch my online business adventure, and actually launch it online, whereas I have just been doing local stuff and found this post very motivating and comforting at the same time.:-)

    Not in a ‘flirting’ in a literal sense, as you did, but in a ‘flirting with something new’ sense and taking chances, getting out of your comfort zone type of way.

    So I just wanted you to know that you are inspiring and helping others in ways you probably never dreamed of.

    Safe travels and I will be reading right along with your adventures.

    I’m not sure if Belize, Central America is on your list of places to go sometime after June of 2012 but we will be moving there (from Arizona, USA) in early 2012, and if so please let me know as you will have a room to stay in!!



    1. Thanks for the comment, Eden! Glad you got something out of this, even if it wasn’t related to flirting. Just goes to show that there are many underlying principles that we can apply to many areas of our lives.

      And I should be heading up through Central America in 2014 at some point, and if your kind offer of accommodation still stands then, I’ll likely take you up on it 🙂

  14. Hey Niall,

    I really enjoyed reading this post. Amazing! 😉 There are so many good advices that can be applied not only to flirting. I like when you say :”To experience the payoff, I had to go through that pain period and keep my head held high.” and is something I’m going to keep for myself, as well as other advices in this post, whether it is in my flirting or in my approaching to strangers.

    Thank you very much for sharing your knowledge and sparing the sleazy parts! 😀

  15. Sang D (@Sangtastic)

    Great experience you had! This is a true COME OUT OF YOUR COMFORT ZONE story! Love this and all the great things you learned along the way!

    I think it is great that you can take an everyday situation and turn it into a learning experience in other aspects of life as well.


  16. I’ve done 2 things that I consider a rarity for me: a) read the entire article b) bookmark the blog. It’s because the post exhibits rare insight and integrity. And it spoke to a part of my human self. Thanks.

  17. That’s amazing! I like the fact you keep the experimenting. These skills can be applicable to any life situation. I will apply it in my MLM skills mastering. Thanks for tips 😉

  18. Ah! Niall this is so awesome!

    The funny thing about doing thing that scare you is once you do it, the next time it’s a little less scary, and the next is a little scary, and the next, and next, and next. Like you said, by the end of those 2 weeks, it really becomes much simpler.

    Pay that price! It is tough, but I think you have to have fun with it. I picture people crashing and burning on comedy shows and it’s quite comical. Sometimes I just picture that. Be loose, have fun and enjoy.

    I think you really have something great going here. This is profoundly inspiring!

  19. This is such an interesting post. I mean the “experiment” alone is intriguing but I really love the things you learned from doing it. In particular the whole pain period. It is a sad fact that most people see themselves as too weak to push through those times, I’ve been guilty of that on numerous occasions and never really took the time to realize it was my fear of going through the pain that ultimately held me down. I’m so appreciative of you bringing that to the light. Now, whenever that happens I’ll remember your words, “Too many of us are hoping for the payoff without paying the price.” {I DON’T want to fall into that category}.

    I also really love the part about accountability! I’ve known the value of this for a while, I just need to find a “mastermind” group who realizes it as much as I do and takes the whole accountability thing serious!

    Thanks for being so inspiring. Your blog is awesome!!

    {Enjoy your travels}

  20. Hello Niall,

    Thanks for sharing, I’ve already known about the virtue of just going ahead and talking to the girl. It got easier for me but what remains frustrating is finding the proper topic to talk about. Somehow, I just fizzle out and I either end up asking more questions or it ends into awkward silences. May I ask how you tap on the right conversation path and keep it going?

    Cheers from the Philippines,


    1. Thanks for the comment, Theo. I still fizzle out like that sometimes, but it’s happening less and less with experience. A few tips:

      1. Have a few stories to tell. Conversations usually stall when one person is asking all the questions, and usually it’s the guy doing all the asking and the girl starts giving shorter and shorter answers. So start telling stories instead. Doesn’t matter if it’s completely unrelated to anything else you were talking about before, just make sure it’s entertaining (“Speaking of Norway, I’ve never been there, but I once went on this two-week road trip across the France and you wouldn’t believe what happened…”). If she doesn’t express any interest in it, just move on.

      2. Introduce elephants. For example, if there’s an awkward silence, make that the topic of your conversation. Be playful with it. If you’re comfortable with awkward silences and see them as something humorous, they’re no big deal. Lean into them. One of my favorite things to say when a conversation dies is, “And that’s the end of that conversation… let’s start another!”

      Hope that helps, man.

    2. Theo,

      What Niall says is spot on. There is no proper topic; or, put another way, every topic is a proper topic. One point to add is to lean more towards statements than questions. Ask a question, if you have to, but after she responds make a statement. Notice how, when you meet a stranger for the first time, both of you ask each other questions. With a good friend, you’re making statements to each other. Make that transition as soon as you start talking. And, honestly, talk about whatever you want. Leaves, seriously? : http://www.youtube.com/watch?v=nIu20j0ecy8&feature=channel_video_title

      Also, I’m in Makati right now — and while it’s harder here than in the states to approach, it’s still absurdly easy, relatively speaking. Good luck!


      1. Thanks! That’s the awesome thing between friends— it’s just easy to drift into conversation on anything about everything and in the end we up laughing and enjoying the company. That is something I’m still learning to integrate with women.

  21. ;)))) I would say – everybody has his or her own way in life ) maybe cause I’m a girl – I know, flirting with either man or girls will give me a kind of result immidiately 😉 or maybe I’m too sure in myself ) Maybe I’m a happy person, but I’m always flirty, so sometimes people say me: Tanya, you are flirting )))))) but I’m not ) it’s a kind of character ))))))

    But as a married firl with 10 years of really LOVE experience, I would say – flirt has a result only when you meet a girl or a boy you feel your second part ))) all other things – it’s a compromiss ))))))))

    1. I told one of my friends that she flirts all the time. Not for evil purposes, mind you. She didn’t see it and would not accept my assessment. O well – it works anyway.

  22. This is a really great idea. I consider myself a super shy person with approach/social anxiety. I’m not looking to pick up guys but I think I’ll give this a try with 3–5 random strangers a day. This will hopefully take out all the pressure and anxiety of making new friends.

    Thanks for sharing your experience with us:)


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  25. You’ve presented some valuable lessons – especially the immersion thing.

    Some of us are born lucky and many ‘people skills’ come easily, but they can always be improved. I’m a combination. Initially quite shy, once I get started I gain trust very quickly. If I could overcome approach fear I might end up being a social mastermind. Cue evil laughter. Nah – I’ll use my powers for good, I swear.

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  29. Hey Niall!
    I must honestly say I was overwhelmed when I read this post. I just felt I had to express my own appreciation for your courage. I greatly agree with all the mind-set you’ve developed throughout life..
    I’ve certainly learnt a lot from this post, I keep up postponing my goals regarding women and I also had this old habit of mine of talking only to hot women, I hope not anymore!!
    Best wiches 🙂

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  33. Hi Niall, I stumbled on this post when I googled Social Skydiving, great read! It is a topic I am really interested in, and I have made efforts to talk to people, (especially cute girls!), through my daily routine.

    One thing I’ve found, and I am wondering if you’ve experienced, is that getting eye contact can be tricky with strangers. A lot of women are seemingly in their own little world and will walk right by without over.

    I find it really easy to talk to someone if we’ve made eye contact, but it seems a little awkward to me when I have to grab their attention some how ie: “excuse me…”

    Do you have any thoughts on this?

    1. Hey Doug. I never really think about eye contact, at least not on the approach. Often I’ll go talk to a girl before she’s laid eyes on me. First time she sees me is when I start speaking to her. That can be awkward, but it doesn’t have to be.

      I hear some people say you should never open with “Excuse me…” because it makes you sound weak and apologetic, but I don’t buy that. You can say pretty much whatever you want as long as you believe in yourself and your body language is good. A girl will rarely remember the very first thing you say to her anyway.

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