Well, I have been meaning to do this for the last couple of days but I just never got round to doing it. Now I have some spare time I have no excuse to not do it.
A bit of background info on myself: I am 20 and currently work as a manager for McDonalds (though I am looking for a new job and have been all 2013 but because my confidence keeps getting knocked I fail at interviews...a lot.)
The last 2 years I have slept with 5 girls, 3 of which I tried to make work with a relationship but for some reason I keep getting screwed over and my head messed with...so a lot of the time I have a bad case of oneitis. 4 of these girls are who I work/did work with so a lot of the time my work environment has been very awkward for me but some how I manage to pretend that I don't care and that I am a cocky arrogant son of a bitch (something which I don't like about myself but I don't know any other way to be.)
So I am not sure how I manage to keep getting girls that I work with, because I struggle to approach girls on a night out or even during the day.

I will start the day I feel that I started taking this seriously...

Saturday 14th Decemeber:
After having an awful day at work (we had our main inspection over the weekend and I failed badly...) I was sat in my car just looking and I saw my friend walking over with her little brother so I rolled my window down and started talking to her and she said that she needed to go into town to do her xmas shopping so I offered to give her a lift in.
On the way there I explained how I felt shit about everything and she said that I should go home get a shower and changed and then meet them in town in half an hour...I reluctantly agreed because I don't really go out much and I had some shopping to do myself.
So after getting changed and all that jazz I drive back into town and meet up with Claire (seems pointless just saying my friend all the time.) and we decided to grab a coffee before we do anything so we go to a cafe we like brought what we wanted and sat down, then she started having digs (taking the piss) out of her little brother for being a virgin still etc and me having my fake confidence act on tries to push him to talk to girls that walk passed hoping one of them would challenge me to do it and break me out of my shell.
Eventually it happens, a cute looking red head walked passed and Claire says "What about her Ash, go talk to her and show him how its done." I instantly know I cannot back down or I will look like an idiot so I get up heart racing, nervous as hell and I finally get there and go with the generic line I have read and watched all over the internet the last month or so:
Me: Hey
HB7: Hello
Me: I was just sat over there and thought you looked cute and wanted to come meet you
HB7: Oh erm thank you
Me: You're welcome
HB7: Is this a dare or something? Nobody does this anymore
Me: No it's not a dare I am just trying to bring chivalry back
HB7: Oh ok, its kind of scary
Me: I am sorry I don't mean to be scaring you, would you like me to leave
HB7: Yes please
Me: Ok no worries nice to have met you

When I sat back down with Claire and her brother and told them that she was waiting for a friend I instantly knew where I had messed up and that I gave up without really even trying...What would you guys have done differently?

Monday 16th December
This was the night of my works Xmas party so I thought it was a prime time to try and approach girls from different stores in my franchise or at least approach someone in the night club after.
The only problem was Hayley (The girl I have bad oneitis for at the minute who fucked me up really bad in November) She looked right at me 5 times at the party and stood next to me at the bar twice and she didn't even say hello to me, its more the principal of the matter...people can still be civil with each other right?
So this got me in a really down mood and i turned to the only thing I have ever believed in since I was 15...i drank...a lot.
A 47 year old woman I work with who I am rather close friends with ended up putting her tongue down my throat...I am not really sure how that happened but I wasn't complaining, shes a hot cougar in my eyes, but after that I went to leave and Hayley just completely ignored me once more so I kicked off and had a go at her stormed out of the party punching a phone box on my way out instantly regretting that decision.
I ended up going to the night club alone and I met a lot of people in there but by this time I was a wreck of my former self, and there was a girl there that I met a couple months back who I stood up for the week previous from a couple guys that were bothering her, she wasn't as drunk as I was but some how we agreed to go back to my place and have sex... It happened twice according to her but in all honesty I cannot remember a damn thing I ended up throwing up a lot, she looked after me until she eventually went home which I cant remember her leaving either because I then passed out.

I need to learn to not drink because of a pathetic girl who does the same thing that hurts her.

What I learned from Monday is that I need to be more confident, yeah a girl has messed me around but without even trying to game anyone I made out with a cougar and also got laid which would have been better if I didn't do a stupid thing.

Firstly, the problem with your approach was incongruence.

That direct approach ("thought you looked cute and wanted to come meet you") works really well if you're actually confident and not nervous. Since you were actually nervous about the approach it felt pretty weird for her.

Next time you find yourself feeling nervous, don't hide it. Admit that you're nervous. Congruency is more important than confidence. This way she won't feel weirded out and she might actually put her guard down.

Imagine a really really confident guy who maintains strong eye contact and has a strong, confident voice. He's slightly smiling and in a very charming way. He's also physically closer to the girl as if he's clearly interested sexually. Then imagine him saying, "I'm nervous because I never approach girls like this before."

Feels fucking weird, right? It's because you can tell he is clearly lying. And when we think people are lying, we assume they're trying to scam us in some way. It's pretty much the same feeling women get when nervous, unconfident guys try to act more confident than they actually are.

The key is to accept how you're feeling at the time, be at peace with it, don't try to hide it, and work with what you've truly got. If you're feeling more confident, go more direct. If you're feeling more nervous, admit it to the girl and find a way to laugh about it and let your desire for her overcome the awkwardness.