I have always been an extremely shy guy. I feared rejection, so I never asked many people out. I had a few girlfriends through the years. Most were just dumb luck in the way we ended up together. They typically ended badly. About six months ago, I finally got the nerve up to ask someone out, and it's been one of the greatest decisions I've ever made.
It's really easy to tell people, "Just go for it? What do you have to lose? No one cares if you strike out. No one pays attention.", etc. In reality, that's not true, or at least, it wasn't. My whole life growing up, I was made fun of, bullied, and every move I made was scrutinized. If I asked a girl out, I was immediately made fun of, regardless of what she said, and she was so humiliated that, typically, she would always be pressured to say no. There were always multiple people doing this, so fighting wasn't an option. Eventually, I just learned to keep my head down and just try to get through life without causing a scene.
This carried on into my adult life with my job. I was very shy, introverted, and constantly tried to stay in the shadows. Luckily, I made some really amazing friends that forced me out of my shell. It's amazing what happens when other people believe in you; you start believing in yourself for once. You start having opinions, making bolder decisions, and eventually taking risks.
It took several years before I finally started getting out more a realizing that not every place was like my childhood. Many people were genuinely kind, supportive, and at the very least, really didn't care what you were doing. Most people were so busy with their own lives that they didn't have time to worry about mine. Several friends pushed me constantly to get out of my comfort zone. I had asked a couple of people out, they said yes, and it didn't work out, but that wasn't the point. Several people said no, several actually, and that was the point: getting comfortable with rejection. I had finally learned that there was nothing wrong with someone telling me they didn't like me, didn't find me attractive, didn't find me interesting, nothing. It wasn't the end of the world. My friends laughed it off, made me feel better, and we moved on to another failure. I actually learned to make fun of myself with them.
Eventually, this carried on to my professional life as well. I no longer fear failure, rejection, ridicule. I learned that it's okay to fail, but the only way to learn something is to keep doing it. I'm not fearless by any means. I still have moments of insecurity, shyness, and doubt. I still have a long way to go as well, but by no means am I anywhere near where I was ten years ago.