I have dated both shy and under-confident men, and men who were both, mostly under the illusion that since they were literary and bookish or seemed to be thoughtful that there were hidden depths and a rich inner life that made them mysterious and interesting, and I longed to get to know them better and discover what was hidden inside. That didn't happen. None of the quiet shy types that I initially thought had those hidden depths ended up proving me correct. Eventually, I just felt shut out. I wasn't meant to be with a shy person.
There is a big difference between shyness and humility in my opinion. TheBF is not shy at all, but he is so humble about his accomplishments, but proud of them, too, and for good reasons. He doesn't display an attitude of superiority to other people, which I intensely dislike in anyone, but he's so obviously confident the way that he is so fearless in his approach to life and his career, his natural leadership abilities, and his ability to make Really Huge Decisions and never look back. I could not do half the things that he does because I would be second guessing myself all the time and I would not be able to handle the stress, but he has the ability to face the potential consequences without fear and make those decisions and not end up being a frazzled stressed-out wreck at the end of the day, like I would be! To me, that shows real, actual confidence, not a facade of confidence like most people display.
There's also a huge difference between confidence and arrogance. That jerkassboy my friend dated was possibly the most arrogant person I've ever met in my entire life, but his arrogance was so transparent. It was obvious that he suffered from a lack of confidence and that he was over-compensating. He seemed to believe that if he displayed enough arrogance, that he would be demanding respect from other people, and that would somehow help him out socially and in his career, when his arrogance was simply a display of disrespect for everyone else. Ugh! I'll never forget the time when we argued over it. He told me that he didn't believe that anyone deserved any respect until that person proved that he or she deserved it, and it was okay to be rude to people who were "nobody" (as I suppose he thought I was when he tried to pick me up in such an insulting way, not realizing that his future SO would be one of my good friends) so I watched as he literally burned bridge after bridge with people who actually could have helped him out socially and career-wise because he acted like a jackass towards stranger after stranger whom he didn't realize might have been helpful to him someday, which seems so just and karmic.
And there's also a big difference between being outgoing and being confident, although a person can have both, like TheBF does. The jealous guy that I loved but whom I could not convince of that, he was outgoing but lacked confidence and he constantly suffered from insecurities that he was not as desirable as other men, or that other people looked down on him. In the end, he became so self-absorbed with his own feelings of inadequacy that he acted intolerably selfish all the time, incapable of thinking about anything other than how he felt about a situation, never what other people were experiencing or how his behavior affected others. There is a level of insecurity that makes a person absolutely selfish and so self-absorbed that it's not possible to have a healthy relationship with them. They can't see past their own noses.
I suppose I need someone who is the opposite of me! I need someone outgoing. I am much shyer than I would like to be, and sometimes it requires effort for me to be outgoing because I do feel insecure or worried about how I'm being perceived. I hate that about myself. TheBF is naturally outgoing, and I admire that so much! He makes friends with people so easily. He's so good about showing interest in other people when they meet, and he treats everyone as his equal and habitually sets other people at ease. There are little friendly and kind things that he does that impressed me about him when we first began dating, things that showed his confidence and his humility and his outgoing nature all at once. Most people ignore the guy at the register or the person walking by struggling with a package who needs a helping hand, but TheBF looks them in the eye and habitually does little things to help strangers out, like helping to make change or carry a bulky package or hold a door, and he makes a joke to establish a rapport with them and easily engages in conversation with anyone about anything, like with other people standing in line with us, which makes even the smallest interaction with him really uplifting and nice, and sometimes, those people that he's been chatting with end up being friends. I admire that ability to do that and I wish I was more like that.
So, yes, I've given shy guys a chance, but I don't believe that we were compatible and eventually, I stopped giving them chances altogether. Every guy I've been happy with or been with for a long time has been the "more outgoing than me" type.