Hey I know this is a older thread but I wanted to put my two bits in. I am a 40 m that used to weigh 354 a lot of that was muscle mass that I gained from power lifting and the other part is I used to be a flat bed truck driver that I used to lift tons of heavy equipment on a daily basis I quit driving truck and now weigh 271 but I don't have and body definition. First I was wondering how the weight loss is going op? I hear you on the lack of confidence as I suffered from that in my youth now this might sound silly and feel silly but this worked for me so while I would be brushing my teeth in the morning I would look at myself in the mirror and say nothing but positive things about myself stuff like I am good looking and I am smart. Now this took a little bit of time but I really started to believe what I was saying. I don't do that much anymore but if someone came up to me and was to ask me if I thought I was ugly or good looking I would tell them I am the hottest one around. Now from what I could see is you are socially awkward so instead of going to a bar or club full of chicks to pick up one or of your luck two go to a sports bar and start talking to some dude. Now the reason I am saying this is so you can build up some social skills and heck you might make a few friends and who knows down the road they might have a sister or friend that they can hook you up with they might even have a gf that could hook you up with one of her friends. Another place you could try is church for friends or a girl. Now as far as going to clubs you need a nice outfit I would suggest a pair of black pants that you find comfortable to wear and a loose fitting button down shirt I like a shirt with a pattern I like longer ones so I don't have to tuck it in. Oh and you are never to old to go to a club. You just need a little swagger man and that will come in time. Also if you get shot down don't worry about it I don't like to be aggressive when hitting on a girl I like to buy them one drink and get a conversation started and go from there. If I was near you I would take you out to party.
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