(what do you mean when you say "meet" ... I'm sure it's not a person you found on the street but someone you are taking the time to know well... right?)

SPEAK UP !!! Wrost thing you will recieve is something like " are you freaking crazy?!?" ...and let's face it, you will survive that. 

Another thing : even if you prefer not to say anything try not to look at that as a mistake or something you are missing, you just didn't choose to take that opportunity and that's fine too. 

i know...but keeping silent means missing...

as Roxana says it depends, and usually it depends on both sides, I mean if the other side is easygoing, it's easier to have a conversation, but if he/she isn't talkative and doesn't know how to initiate, it gets a bit difficult, especially if you're like him'her too

It depends on the circumstances, though I'd rather prefer to speak out than keep silent.