why do I feel so bad?

for the last few years ive really felt down overall, diagnosed with severe depression since i was about 16. in my early 20's now, and since i was teenager ive had self-esteem trouble, lack of confidence because ive felt ugly, still trying to figure it all out, why i feel this way. however, i was able to get with attractive women in high school and didn't have to try too hard, girls who were 'popular' and desirable, but it seems because of my own insecurity i came off as "uninterested" of these girls because i was shy, i didn't know how to approach girls because i was mostly approached. in return these girls must have thought I "dissaproved" of their "looks," as if they weren't "good enough" for me, or too ugly. i wasn't really aware of this though, i didn't understand how my insecurity affected others by appearing to be sad and therefore displeased and unhappy with the relationship, when in reality the problem was within myself, i thought i was u gly but failed to realize that if these attractive women were willing to date me, or hook up then i must be good looking to some level and shouldn't feel so sad. the sadness came from a thought that i can never change my looks and who i am, and if im ugly then i could never be with a beautiful woman... i dont know why beauty is so important to me, it represents something.. anyway... recently, i am trying to see the positive about myself. i dont want to feel bad, i want to love and be loved, something real, something with substance and unconditional care: happiness. ive started to come to grips with reality, life and death. ive only got one life to live. its a long story, to make it short i recently i got a new job in a skilled trade working harder than i ever have. ive started to get this new confidence being around working dudes, i started this months before i went to the place this girl works at so i feel like ive become more skilled at what i do, and this confidence seems to be transferring to my daily life. ive felt better. i saw this girl at a small business, shes a clerk kind of position. first time i saw this girl i was like wow, i want to know you. but talking to her? how would i even start a conversation? since highschool i stopped talking to most of my friends, for a few years haven't been meeting a lot of new people, especially girls. ive become rusty. there was some small talk after i was about to leave the store, just starting with "hey," but it was almost like she was calling me over, inviting... i DONT KNOW!!! am i just crazy? it was like a "heyyyy".... god damn im clueless... somehow, i told her my name, that im new to the area. she told me her name, was friendly, seemingly flirtatious rather than friendly, thats what it appeared like, genuine, not an act. but i was held back, i didnt know how to take it further than that, should i have waited it out like i did, kept it cool? it was a brief conversation, i made an exit and she said she'd see me around in a smiley manner.. ugh.. i don t understand these social situations... i dont want to say the wrong thing, i want to say the right thing. i am fearful, but trying to overcome and face this. im trying to let it come naturally and not rush anything, but this seems to be painful because of time, i feel lonely. i hate being alone, it feels like no one is there. at the same time, i really want to say "wow, you are so beautiful, your eyes, your hair, that smile... you are an angel, and that laugh.." but i feel like ill come off as a creep, as a strange man... then i went in today, didn't even want to because i became afraid, and i forced myself to go. my god, she was there at the front. i was kind of shocked, she seemed flirtatious again, smiling, leaning over... and i tried keeping it cool, just staying relevant to why i was there, when really inside i wanted to break the barrier, ask her out, but the fear overwhelms me of rejection, prevents me from climbing the mountain before my mind. i made small talk, then went into their office for a few minutes to get something, came back out and she was on the phone. i am a customer there. she said "one second" to me. i was going to ask a simple question to make small talk, to initiate the conversation maybe into something further, like a phone number. i was open to whatever came, not having really any expectations.. but then some guido looking guy came in trying to show off his muscles, and immediately this girls co-worker came out and asked me what i needed, i said something retarded th at would have only made sense to the girl i wanted to really talk to. the girl was still on the phone, i just turned around and left. i didnt want to come off as a weirdo standing around there waiting to talk to this girl, i feel like such a failure though. why do i feel so shitty? i cant even explain it, i forced myself to talk to a girl like that... it took so much out of me to do that, and i was trying sooo god damn hard to overcome my problems, and then it got fucked up when i attempted to know this girl further. i feel like absolute shit, i got into my car and screamed the loudest i have in anger in a long time, turned up some loud metal and just screamed, im so pissed off. i feel like ive failed, i feel like ill never get another chance again. why do i feel so sad? i just want to cry, i dont know why i got like this, so down in the dumps.

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