Aw shit bro. Been there :(
"Well, son... it's better to regret something you have done than to regret something you haven't. And if you see your mom this weekend, be sure and tell her 'Satan!'" -Butthole Surfers, opening of "Sweat Loaf" It's true. I learned when I was in sales that you go for a close and expect a 'no'. Don't fear the no: embrace it. No is not the end because it's not the end of the conversation: it's a starting point for handling objections. If the person says 'no' and walks away, then it's even better! Why? Because it's totally over. Now you're free to start the next attempt. You don't even need to look back: be polite and move to the next event. Sales taught me how to flirt and ask people out. It taught me how to read people, almost as much as spending time in a place where I barely knew the language. I tried and I grew from it.
Go for it, and then you guys can end up like me ;) Just kidding. Seriously, go for the romantic adventures. Go for all adventures. I believe in saying yes to things - especially any theoretical plans anyone ever suggests. (Unless it's like, let's go kill a human.) It gives you a list when this question comes up, but it also means you're continually entertained, have great stories to tell, and if you are intelligent and reflective, you learn from everything you do. You learn more about yourself, more about the people you're interacting with, more about the way things make you feel... And you will never (hopefully) feel like you are missing out on life.
Amen. That, and to no longer throw your balls in the trash and run away when you have golden opportunities to talk to a girl :(