Dear birds of a feather:

“A friend (not sure if we are still friends) just started a new job and we are no longer in the same social circle“- having read the rest of your post, seems to me that he was a job & social circle friend.  Since he is now in a new job and a new social circle, he is an acquaintance, no longer a friend.

“I have this feeling of him not wanting to invest time and energy into this relationship – which is incredibly hurtful to me for some reason“-maybe his lessened interest and availability triggered an old hurt, maybe a parent’s loss of interest and availability to you..?

“I’m not sure how to respond to his question of how about meeting up at so and so date (two to there months away)… How should I respond?“- I think that you feel too hurt to  act as if you are not hurt. If I was you, I would tell him about how I feel, I would say that I feel hurt (I wouldn’t elaborate and say to him, at this point, “feel very hurtful”, or “incredibly hurtful”, your words in the post) and see how he responds.

What do you think about my suggestion?

anita