My Top 10 Player Fails (Part 1)

It occurred to me recently that I write a lot about my success as a Player but I havent really touched on all the cringe-worthy failures that I experienced on the path to become a Player.

I look back on many of those failures now and I can only laugh and shake my head at how hopeless I used to be with beautiful women, I mean I was bad, really bad. A lot of the guys that I meet say they have trouble picturing me as being anything less than a very confident capable guy, but we all start somewhere and there was indeed a time when I was quite socially retarded to say the least.

All of those failures although unfortunate at the time, paved the road to my future success and despite the embarrassment and heartbreak I went through as a result of these failures, they helped make me the man I am today, so I wouldn’t ever dream of taking them back, even if I could.

I know that some of you reading this might be in the aftermath of some epic failures yourself but this just goes to show that no-one is perfect and in order to the best at something you need to go through some tough times to get there.

These were some of my toughest times, so I hope you enjoy them and just remember a mistake is only a bad thing if you don’t learn anything from it.

Player Fail 1. The Love Letter

When I was in Year 10 at high school, I had my first serious crush on a cute blond girl in my class named ‘Jamie’. I didn’t have a lot of confidence back then and most of my friends were pretty nerdy and I generally had no idea when it came to dealing with beautiful women.

Every time I would go to class I would look longingly over at her from where ever I was. Occasionally I would work up the courage to sit next to her but then when I did, I would get tongue tied and the only thing I could say to her was ‘Do you have a spare pen?’ or something along those lines.

I never had the courage to make my move and then soon enough Valentines Day came along and I had so much to say to Jamie about how in love with her I was but I didn’t have the courage to even approach and talk to her.

So I wrote her this letter telling her beautiful and amazing she was and how I was her secret admirer but I lacked the courage to talk to her because she was so devine.

When she got this letter, rather than keeping it to herself or finding me and revealing her ‘secret undying love for me’, instead, she showed it to everyone in the class and one of the ‘cool kids’ recognized my hand writing and despite me vehemently denying it, I was teased about it for the rest of the year until I changed schools.

Player Fail 2. The F*ckbuddy

After I changed schools I started getting involved in Rugby and working out at the gym and after awhile I started to develop a pretty impressive physique.

When I was younger I had always been ‘the fat kid’ and I used to get teased about it a lot, so when I went from being the fat kid to the muscular kid I developed a bit of  a fascination with taking my shirt off every chance I got and on such occasion when I took my shirt off at a party, it happened to impress one of the shallower prettier girls there by the name of ‘Nicole’ and she decided that she wanted me.

So that night she was being very keen but I hadn’t even kissed a girl by this age, which was pretty pathetic in itself considering how many wasted opportunities I had been given and Nicole mistook my shyness for disinterest and even though we didn’t hook up on the night she became even more infatuated with me when I seemingly rejected her advances.

Of course I didn’t actually reject her advances I was just so scared of having my first kiss that I actually conned myself into believing that I wanted to get to know her first or I wanted my first kiss to be special, all the usual bullsh*t guys tell themselves when they are just too terrified to make a move.

So that night nothing happened but she managed to get my phone number off one of our mutual friends.

A day later I get a text message from her, asking me if I wanted to be her ‘F*ck Buddy’, at first I thought it was some kind of cruel joke but then after some back and forth texting I realized she was for real.

So we organized to get together and sure enough I met up with her after school I went back to her place, sat in her bedroom but I just couldn’t muster up the courage to make a move so instead I made lots of small talk and ended up staying for dinner with her parents instead of shagging her then and there like we had planned to.

After that the window of opportunity closed firmly shut and for the next few weeks I kept trying to meet up with her with the idea of becoming her boyfriend but instead I got the ‘I think we should just be friends’. I was so bad with girls back then I had it handed to me on a silver platter and I still couldn’t make it happen.

Player Fail 3. The School Dance

In the last year of high school I was still a virgin but interestingly enough I had developed a friendship through MSN Messenger (what my generation used instead of Facebook) with a hot girl from my old school who I had always had a crush on but had never had the balls to make a move because she had dated a guy I knew but wasn’t even friends with, that was my excuse.

We had a School Dance coming up and I didn’t have a date, so I figured why not ask her.

What I didn’t realize at the time was that Lisa had actually had a crush on me for awhile in fact there had been many occasions when she had tried to spell it out to me but I had dismissed her advances as friendly because I couldn’t understand why such a cool beautiful girl would be interested in a loser like me.

So when I asked her to the School Dance, she thought that I had finally mustered up the courage to make a move and she was wanting to meet up and go out (which I thought was just a friends thing) and when we did meet up before the School Dance for a movie, I decided it would be a good idea to bring my friends with me.

This and a lot of similar incidences gave her a whole lot of mixed signals and as the School Dance got closer she began to realize that I had only asked her as a friend and I continued to believe that she wouldn’t want anything more.

The final nail in the coffin was when a week before the School Dance I met a hot girl because we had gone to her place by mistake on a way to a party which was actually across the road. After she answered the door and explained  to us that it was the wrong house for the first time in my life I decided to be brave and I asked her for her phone number. This was the first approach I ever did and she gave me her phone number and I went to the party across the road.

Then an interesting development occurred, one my friends didn’t have a date for the School Dance and I had the bright idea of inviting this new girl I met and I could talk Lisa into going with my friend because it would be the same kind of thing.

So I asked new girl and she said yes and then I told Lisa and I was surprised at how disappointed she seemed at first but she covered it up well and said it was fine.

So School Dance night comes around and I’m there with the new girl and Lisa is there with my friend. I’m still too much of a wimp to make a move on the girl that I brought and when I do try talking to her about the possibility of dating (instead of making a move) she tells me that she’s interested in another guy and then I turn around and I see Lisa making out with my friend.

Because I didn’t have the balls to be a man and make a move on either girl, I lost both of them and Lisa ended up going out with my friend for about 2 years, the whole time I was secretly in love with her.

I found out later in my early twenties that Lisa had always had a crush on me and that I broke her heart when I palmed her off to my friend at that School Dance . Eventually I did up sealing the deal with Lisa but it was about 4 years too late.

Player Fail 4. The Almost Threesome

Recently I released an article detailing my threesome stories and then another article explaining my tips for getting a threesome based on the lessons I have learnt along the way but what I haven’t told you about is all the threesome fails that I had before I actually managed to pull it off successfully and this is the most prominent of all of them.

When I turned 18 I finally lost my virginity to my first girlfriend (our relationship lasted about 1 month) and since I was now at an age where I could drink and go out, I started getting into the nightclub scene in a big way.

At the time I was also doing a lot of hard labor for work and I was in very good shape, I was getting a lot of really positive attention from girls and I didn’t really know how to handle it.

One night my friends and I went out to a nightclub we had become really fond of because a lot of our school friends went there and they had a 2 for 1 deal with drinks until 10pm so alcohol was really cheap and we usually had a pretty good time there.

In the 10+ times that I went to that club, not once did I actually approach a girl but occassionally they approached me. On one such occassion I was sitting in a pod waiting for my friend to come back with drinks and two beautiful women came over and one sat down next to me and the other sat across from me.

The more confident of the two then told me, ‘We’re lesbians and we want to have a threesome tonight; we decided we wanted that to be with you’, I was stunned I didn’t know what to do, so rather than getting in a taxi with these beautiful women and having an amazing threesome experience, instead I got flustered and I said, “wait here, I will get my friend, he’s good looking, then we can have a foursome”, I went off to get my friend and when I came back I realized that they decided not to wait around and probably found some guy with balls.

Once again I was handed an incredible sexual experience on a platter but because I was too much of a pussy to man up and make it happen, it didn’t happen and I went home that night alone and angry at myself.

Player Fail 5. The Irish Bartender

When I was approximately 19 years old my journey to become a player really began when I embarked on a six month trip overseas with high expectations and some seduction and dating books to read during the trip.

For the first couple of months I had no luck at all, the first pretty girl I almost kissed ended up throwing up all over my shirt and I spent the rest of the night trying to make sure she didn’t get kicked out of the hostel we were at. Even after looking after her and cleaning her vomit off my torso I was still friendzoned the following day.

Every hostel I went too I was approaching girls like crazy, I was trying out all sorts dating and seduction theory and none of it seemed to work the way was supposed to, sure it got me out there trying in the first place but two months into the trip and I still hadn’t had the opportunity to use any of the 50 pack of Trojan condoms I had bought for the trip.

Then in Argentina I finally had my lucky break. I had decided to take a step back from the whole dating and seduction thing and I wasn’t trying so hard to pick up girls I was just concentrating on having a good time and making new friends.

The confidence that I had developed from all my earlier seduction attempts during the trip had made me into a really sociable guy and I had lost a lot of the anxiety I had when talking to beautiful women because I just didn’t care anymore.

One girl in particular found this attractive and she just happened to be a stunning Irish bartender by the name of Serena, who also happened to be a professional model and dancer back in Ireland.

When I met her we got along great straight away but as I soon found out, she was very popular and got on great with everyone there. She was also enamored by just about every guy in the hostel, everyone wanted her and lots of guys tried.

It’s funny because when you’re a single guy backpacking around the world, every time you step foot into a new hostel it’s like starting on the first day of school, nobody knows you, lots of people are interested in you and you spend a lot of the time trying to differentiate between the cool crowds and the uncool crowds.

Sometimes I would go to a hostel and I would do something lame to put myself in the uncool crowd but sometimes I would go to a hostel and with new found confidence I would go straight to the top and every place I went to this seemed to change and the longer I stayed at one place the more complicated things became.

So at this hostel in Buenos Aires, everyone thought I was pretty cool because I knew where they could get cocaine and this was an instant in with the cool crowd there. I was being sociable and cool and people were enjoying my company and a couple of pretty girls there were interested in me but I only had eyes for Serena.

One night we went out to a nightclub and there was a big group of us and both of the girls at the hostel who were really into me came along and since it was myself Serena and these two other girls in a taxi together on the way there, she noticed that they were competing for me and she suddenly became a lot more interested.

So we got to the nightclub and everywhere we went the hostel crowd wanted to follow Serena around and I realized that this was my window of opportunity, if I was going to have a chance with this beautiful Irish Goddess then it would have to be at Club Pacha in Buenos Aires.

So I came up with a way to isolate her from everyone else and I got to show me some dance moves and as she was getting close to me I decided it was now or never and I went for a kiss half expecting to get rejected but knowing that if I didn’t then I would always have to live with that regret and that would be unbearable.

So I kissed her and she kissed me back and that night we went to the hostel and we had great sex, and then we had sex again the next morning and for the next week I tried to have as much sex with her as humanely possible because I feared that she would eventually realize that I was unworthy and she would dump me.

Well if you believe in something strongly enough then generally it will come true for you, it becomes a self-fulfiling prophecy and it work both positively and negatively.

Because I believed I wasn’t worthy, I became jealous and insecure and what could of been something beautiful and amazing with a really cool beautiful girl turned into something ugly and awkward and I was so heart broken when she told me our little fling was over, that I packed my bags and I headed for Europe.

You might be thinking… How is that a failure, you got to have sex with a cool, beautiful Irish bartender?

Well the reason I believe that was a failure was because I wasn’t the strong confident man that I should of been; that I NEEDED to be in order to see it through and make it a positive experience.

One positve though, was that I learnt a valuable lesson, ‘if I don’t believe I am good enough for beautiful women, then why would they ever believe that I am good enough for them?’


These aren’t the only stories of Player failures that I have either… I have hundreds, thousands but most of them I don’t remember because I learnt from them and I moved on. And because of that, even though I may have failed in these little things, I have won in the big things because I didn’t let these little failures stop me from achieving my destiny as a man instead I used them to propel myself forward to better and greater heights.

There is no shame in trying but there is shame in not trying, if you’re at a place in your life where you’re not failing then you are not growing as a person either.

I hope that my stories have inspired you to make some of your own Player stories because one day when you are old and grey these stories that you make now, these crazy things that you do while you’re living your life to the fullest; these memories will keep you happy in your old age because you know that you dared to live and be the man that you wanted to be.

By Kieran Black


Click Here To Read Part 2

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