Maybe because in the first chart Jupiter (him) is applying to Saturn (her) but she goes retrograde, but then he goes retrograde too, their meeting will not come to pass. Maybe, just trying to figure it out.
there is TOL in both charts
that is the problem.
if there was no perfection of an aspect, I would have said something.
plus saturn and jup wlll reunite once both planets begin to chase one another
take a look at empheresis to see when that happens.
NOT saying that you should be freaking out but the fact that his reaction is emotional (he hasnt made peace with his past) is worrysome.
There are 3 stages in post breakup : going over your mind all the pain one caused / what did i do wrong? / why he/she broke my heart 2nd stage -- complete numbness 3rd stage - letting go and opening the doors for the others.
Normally, you would say I let the pain go or we had the good and bad times but things change and people change.. here it is like an auto anti-body (i dont wanna talk about it or however else he says.. you got the drift) .. out of personal experience if if a person you are dating has that kind of reaction i'd wary of how this relationship will evolve. you are not his post breakup therapist nor you are his rebound gf
Keep your eye on his attachment styles communication. Is he emotionaly opened. Does he speak freely about how he feels? Is he the one that comes over and hugs you? Little things that shows he is confident and comfortable with you, less chances of him to have you as his rebound gf. if he is like a condesed milk, then you have a problem.
You want a secure bf. Anything less than that will get your wheels spinning and you might be wasting your time on fixing him (not your job).
I hope you get my drift.