I suppose nobody can know that for sure. Sometimes people do expect things to be "weird," but something in their heart says that it would still be worthwhile. ;)
In any event, I hope that you find the courage one of these times — if you do want to see him again — to take him up on or to extend one of these invitations yourself. If your heart seeks some kind of closure or resolution, I hope that you find it, and in the best of ways.
Thank you for being so vulnerable with your own story, Lola! And may life eventually bring you an enduring, requited love that erases any sadness for loves-past.