Sometimes... it's like getting into a cold pool. You just got to jump in. No dancing around. No pussy-footing in. Just dive.
For example, I remember being in a church once and I just decided I was going to go up to people, tell them I was new, and introduce myself. That broke the ice fast. I do not always do this, but doing it has usually turned out to be a good choice.
Another example... I remember, maybe... 9 years ago (Sept 2012?)... I encountered an attractive Filipina in a laundromat (I mention her ethnicity because I have a preference for what I, as a westerner, would call 'exotic'). We had a little rapport going on throughout our time there and decided I wanted to ask her out.
Ask out a stranger, right there, now?!? Just throw myself out there?? Yes. I decided I would do it.
But, I told God I needed an "in". So, as I got ready to leave, I said something along the lines of 'Good night,' and I told her my name (Keith). She said, if memory serves, that she was Brittainy, and that it was good to bump into a stranger who was nice. That's an 'in' if ever there was one.
So, I said, "Would you like to get to know one another a little better?" She looked away, closed her eyes, looked back and said, "I'm sorry, I'm taken." I said, "Oh, alright then," and picked up my basket. But, she said, "Maybe we'll bump into each other again." That made no sense to me. I mean, why even consider that? So I answered, "I hardly ever see the same person twice in a laundromat," and I walked off, clearly with a changed demeanor.
But, I was happy. Why? Because I walked through a door when it was opened. The worst that was going to happen was that she'd say 'no'. I couldn't brush that off? C'mon. Despite the disappointment, it was worth it.