Alright, story time: I had to learn a lot about taking risks before me and my girlfriend started dating. I knew her for about 4 years but we didn't become friends until about 3 years ago and I soon developed a major crush on her. I had a ton of competition (mostly guys like me) and she didn't really think that much of me. I was shy and watched as she dated other guys (both were abusive and it hurt so much to watch this). She moves in with her newest boyfriend and signs a two year lease with him and his friends despite everyone saying it was a bad idea. She gets stuck in the house and, to make matters worse, she breaks up with him only a few months later. About two years ago I noticed her going through a serious bout of depression and talking about it on Facebook. We had never had an extended conversation at that point but I got her number from a mutual friend and found the courage to call her to tell her that if she ever needed someone to talk to that I was available. We start talking on the phone and Facebook almost daily and see each other several times a week. About three months pass and I, kid you not, one of my professors and classmates made asking her out an assignment for me as part of my Group Therapy course. I ask her out and tell her how I feel. She LITERALLY laughs in my face... but I take it surprisingly well.
We stay friends. We still talk and I end up dating someone else for about a month. That relationship failed to go anywhere largely because it was obvious who I really wanted to date. I didn't want to give up on her. I spend the next 3 months helping her move out of her abusive exe's house. She sees that I'm genuinely concerned about her welfare and we start seeing each other daily. Things start getting pretty serious. I take an ENORMOUS gambit and use the L word. She starts pushing me away, saying she's afraid that I'll eventually hurt her. I take yet another chance and tell her that I want her to be happy, even if we just stay as friends. After a month of debating, her coworkers and my friends talk her into it. I take her on the boardwalk in my town on a cool October night, sing Van Morrison's Moon Dance to her, she tells me she loves me too, and we kiss in the rain. Cue credits.
Lessons learned: step out of your comfort zone, take risks, not every setback is failure, and, jesus pancake flippin' christ, confidence is essential.