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Confidence confuses me

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Just turned 30 and to be fair I had a family death a few weeks before my 21st, then a year long murder trial/wait for the trial then people in local town saying my family killed them and covered it up.

Because of the shock to my system that was I basically stalled my confidence growing for a few years and I went back to uni aged 25 then dropped out and tried again age 26 and 27 then college 28 and 29 but I just get self concious being around 18 year olds who talk about how great their lives are.

Anyway going back to when I was 17 and I first left home, I felt so good that one day I told myself that I am a good catch for a women so suddenly switched on confidence, that lasted a few days of me just being confident and flirty and even getting a few girls phone numbers then one day I thought to myself "what if I am not good looking and women dont fancy me?" that put me back down again and I was unable to directly turn it back on.

When I was 20 I started gaining some self esteem, started clubbing every week and flirted a little but was a little shy to chat women up(though did get a few numbers) until the death put me right down which I never recovered from.

Anyway what I was thinking was its all a frame of mind, I did it when I was 17 and built it up slowly aged 20 so it seems personally to me its just a case of believing what I say so I have no doubts, I am so used to knock backs that I do not try or if a girl does fancy me I do not chat her up as my mind races with reasons why it will go badly.

How can I make myself put these fears at ease apart from the logical just try it since that is what freaks me out!

Any advice would be appreciated.

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