Thanks for all the replies guys. I definitely think going to a therapist would be a good start for me. Like I said though, I think I'd have big trouble talking about my problem to someone else. I'm also worried that if I'd go to a therapist, and I wouldn't be able to tell the whole thruth, I might not actually get the help I'd need. This is why I've started thinking what the best way for me to do this would be. Maybe I could exercise what I need to say on the first session, like a speech (which I really hate holding myself btw). The other thing I was thinking about was that maybe I could write it down, and ask the therapist to read it? I've never been to a therapist before though, so I'm not sure if that'd work. As for meeting someone spontaneously as you called it, I'm guessing it's one of the most common ways to start a relationship, but here's the main problem as I see it (If we take an example out of a movie): A man and a woman bump into eachother in the street, the woman carries a pile of documents, they fall down all over the ground, the guy immediately apologizes and starts helping her pick them up, they look at eachother and smile, they start talking, have a cup of coffee and whatnot. Here's the version with me: The same thing happens, I bump into the girl, I apologize and help her pick the documents up, however, my guess is that 99% of the time I'd be too scared to actually smile at her in the first place, which in turn would'nt make the rest of the story happen in any case. This was just an example, but something I've noticed over the years is that most women don't seem to think shyness and poor self-esteem are very attractive attributes, and I've got both of them in abundance.