How do you tell if someone is pleased to hear from you?

[tallulah2014]

OK, rubbish title I know.

I'm a fairly shy, socially awkward kind of person and I find it almost impossible to talk to people, either in person or via message/text.

I'm in an awkward Facebook conversation at the moment that isn't really going anywhere and have no idea how to get it 'somewhere. The person I'm talking to is someone I had a fling with years ago and who always speaks to me when he sees me around town (only once or twice a year, but he is the one that initiates conversation, calls me over if he sees me, etc).

Anyway, I just sent him Facebook message asking after him, as it must be at least 2 years since we last spoke. He's replying, but in a polite "what are you up to" kind of way. Ideally, I'd love to be, kind of... friends with him. He's single, as am I, but I don't know how to get the conversation moving and make my intentions clear without either making myself look full-on and creepy, or sounding like I'm hitting on him!

Can anyone offer any advice, as I've run out of things to say :(

If he’s responding then he’s pleased to hear from you.

Stop tying yourself in knots and just ask him out for a drink.

Forgot to add; I don't know whether he's just chatting to me out of politeness because I messaged him first, or whether he actually wants to talk to me - he keeps asking how I am, what I'm up to etc but I can't tell whether I'm kind of forcing him into a conversation he would rather not have, or whether he is enjoying talking to me. If that makes sense.

As I said, I'm socially awkward :/

Ask him for a drink/walk whatever date activity you like and see what he says.Good luck!

But you are hitting on him .

Just be straightforward and suggest a coffee sometime. If he says no or flakes out, then you know.

Ha, I was going to say the same - you are hitting on him. Own it and ask him out.

What have you got to lose? Just ask him if he wants to meet up for coffee