How do you know you're forcing yourself on to someone?

There's this guy I've known for about two years, but we didn't really talk one on one since he's my friends' friend. My friend has been trying to match us (mostly jokes). Recently, I sent him a friend request, and we've started messaging each other.

He told me before to let him know if I want to game together or to give him an update about things that have been going on. This gives me the impression he is interested in talking but is waiting for me to take the initiative. Which makes me wonder why?

How do you know a guy is interested in talking, or is just replying out of politeness?
How do you know you're forcing yourself on to someone?
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