I don't know that it will do this thread's OP any good to hear this, but i am nearly 27 and have also never had a gf. A lot of what you said parallels my own life, I get very lonely, you beat me with the at least having many girls who were friends (i'm lucky if I have 1 or 2 friends in my entire life, both being guys) .. i'm not trying to trivialize your plight, just maybe try and look at that as a positive in your life?
Same thing happened to me in grade school with a girl i liked and i've never got over it and rejection fear is so great I can't even attempt to even talk to a girl never mind flirt with her.
Basically all i'm saying is you have my deepest sympathies, I wish I could offer you more, but maybe you can get some solice out of knowing you're not alone (it helps me sometimes to know i'm not alone, though its the meds i'm on that have probably kept my head above water, I have no passion, desire, or positive emotions in life because of them, but I also don't suffer the crushing depression I used to contend with constantly every day)
I find it especially hard when i'm around someone who trivializes the whole dating component of life, I know they don't mean harm, but most ppl when they talk about relationships shrug them off as something that happens all the time in their life and their current gf/bf is just another in a string of normal behaviour in life ...
Anyways, i'm sorry, i'm not trying to hijack your thread, I hope some of this babble might mean something, i'm here on this thread today cuz I am feeling particularly lonely and worthless lol (after someone went on for an hour about his past relationships and how trivial they are apparently last night to me).
Anyways, I will hijack your thread for a second (sorry ), if any girls around read this and want to TALK (i'm not talking about dating, I just want experience/practice talking to girls, as well as a girl to confide in) .. and would like a friend who is a girl, please feel free to PM the OP (i'm not that mean to take this thread from you, heh, just don't know how else to go about this whole madness) or me .. you would make this sad heart's day