If you look back at the last few relationships you’ve been in, you can see a pattern: you seem to always be attracted to emotionally unavailable men.
Despite your best efforts to get them to open up, you always end up hurt and frustrated that they never reciprocate the affection or love you feel for them.
When something happens that you believe should have a significant emotional reaction (his dog died, his brother ran over his foot with the car, his roommate drank his beer), prod him gently for a reaction.
He can (and likely will) defer the question, but at least you’re making an effort to engage in dialogue about his feelings.
I’m not saying he needs to buy that homeless lady a house, but maybe throw her a few coins and appreciate that she’s down on her luck. He should realize that people make mistakes, and if his waiter gave him the wrong order, politeness would remedy the situation better than anger.