CastleRock, I'm a firm believer that when those situations occur, it's because that person has something to teach you, or tell you, or whatever.
The universe may keep putting him in your path until you resolve that lesson. Or, you may lose your opportunity to, if you don't find the nerve to *make* it happen.
MAKE it happen! What's the worse that can happen, you'll feel silly? Look silly? So what! What's the best that can happen? He could be your ideal mate, and you've yet to find out his name~!
So do it!
I walk up to strangers all the time! It's fun! The only trick is to walk straight to him without hesitating, and then smile right at him, right into his eyes.
Go up and say, "You don't know know me, but..."
Or, "Hi, my name's ... I see you on the bus all the time, what's your name?"
Or, "You seem to take the same bus as me a lot, hi ... my name's ..., mind if I sit with you today?"
Or, "I see you on this route all the time, where are you always going?"
(I know it's hard, esp. when it's a *boy* but I swear, you can do it!)
(Here's an example of Alissa approaching strangers to make you laugh ... earlier this year I was at a wool festival in Taos and at lunch I saw a woman who looked so much like Janet Leigh I couldn't stand it. I kept staring at her.
Finally, when my friend slipped out to the restroom, I walked over to her table, where she was lunching with a male companion, and said, "Excuse me, I don't mean to bother you, but I just have to tell you, you look so much like Janet Leigh!"
And she started laughing, complimented obviously.
"And, if you are Ms. Leigh, then I want to tell you what a pleasure it is to meet you."
She shook her head, still tickled. "I'm not Janet Leigh! I've never even been told that before!"
I shook my head and smiled back. "You look just like her, you're beautiful," I said and walked away.)