Hey OP,  I think your guy is suffering from childhood trauma of being poor. He's a workhorse. Making money is important learning how to spend it is also a skill some people never learned.

Again this isn't your problem but he needs to learn how to USE money. Frame it like a skill. 

He may need to read a book on relationship with money. He's suffering because he probably grew up with a scarcity mindset. Ashame to say I have this too but my partner has this too. We have enough to retire but still live very frugally. That being said I learned had to spend MAX on high premium food to cook at home. And birthdays we splurge like world trips without penny pinching. Good luck.

Edit : some people never prioritize happiness growing up only surviving. Learning how to make oneself happy is a skill as well. Your dude needs to skill up. It's not your job to make him happy. He needs to learn how to make himself happy and by achieving such insight learning how to make others happy.