My man can't cry!

My fiance is a very sweet, very caring thoughtful and a loving individual. He is sensitive,he listens to me when I talk and is all around amazing. He has ocd, anxiety and depression. He was in the air force. He was raised by his father (who also served) to never show emotion. Whether it be anger or sadness. And to never under any circumstances he should never cry. I understand it was implanted in him as a small child and it's just how it is. But it kills me bc he longs to cry, to have that release of emotion that's been bottled up for years. And it also kills me bc since we've been together I've had 3 miscarriages....they were torturous times that left me huddled in bed, away from my other two LOs bawling for hours. While he, being raised like he was, showed no emotion whatsoever. Which made it worse for me bc I felt it didn't bother him and he didn't care. Idk what to do or what he can do. He's tried therapy and it didn't work. He'll try to cry and it only leaves him nauseous and shaky. I'm at a loss.....help us.....help him....