I agree that it is really difficult to tell. I often misread people's intentions so usually now I'm really cautious. Sometimes I think people aren't interested when they possibly really are.

Just to give an example of what I meant though, you could maybe send a first email / text saying, "Hey its me, I know it's been a while but thought it would be nice to catch up". Catch up is quite a vague term, it could mean meeting, or just having a chat so you've given them the opportunity to expand on that if they want to without trying to pin them down to anything specific.

Maybe not those exact words but something like that. Then it's a case of waiting and seeing what happens. No reply at all probably means they're not interested and you can then move on (although it could mean they've changed their number or it's an old email address).

If they do reply and you're not sure of the tone / what they mean, you could always come back on here and ask advice. Or even PM someone if you didn't feel comfortable posting on an open forum.

If you really like him, I think it's worth taking the risk. Good luck whatever you decide to do.