This is frustrating isn't it?
A couple of years ago there was a girl I used to see semi-regularly 'cos we had mutual friends in common. The first time we seemed to quite like each other but nothing actually happened.
Then the second time I happened to be somewhere where she was, a few of her friends made a point of telling me she was there but when we spoke there was just no real conversation there...
Then after that I'd see her every month or so, there'd be this weird thing where we'd approach each other wanting to talk to each other, stop, smile and then realise neither of us had anything whatsoever to say, then giggle awkwardly for a second, make some kind of banal small talk then escape as quickly as possible.
I'm sure both of us wanted to break the ice but we just never managed it. Has anyone else had similarly frustrating experiences of this?