The Mandate: How to help a boyfriend when he's down on his luck

I have been with my boyfriend for 2 years, and I love him a lot. I'm worried that he might be struggling financially and I want to be able to help him. I'm in a place right now where I can afford to help him out but I'm worried he'll be embarrassed and lash out. What should I do?  Financial struggles are a thing of the past, haven't you heard? The struggling artist is dead! I can only imagine your boyfriend is an artist, or you're hiding the fact that he's unemployed, which, by the way is okay. The easiest thing to do is to sit your boy down and have a little chit chat action, but in reality that's also the hardest. Confronting the matter head on will make that turtle's head pop back in it's shell quicker than you can say, "I support you." The major thing you have going for you in this scenario is time. You two have been together for two years, so there are ways you can broach the subject that make it seem like a natural progression in your relationship. This all depends on how comfortable you are with him, but "I love him a lot," usually means that you love him? a lot. It's around the two year mark that you really should be making the next step into living together. That's also cost efficient as you'll be splitting the rent then/ If he has roommates, you might have to suck it up for a little while, ditch your digs so you can help him out with his. Hey! You love him a lot, right? If moving in together is too big of a leap for you, ask him if he'd be interested in opening a joint checking account. Red flags may go up in his head, but explain that it's not about marriage, it's about reliance. How your partner handles money is a real determining factor on your future together. You don't want to have an empty checking account while little babe Tommy is crying for some warm milk. See what kind of a man he is, and maybe this will explain why he's "struggling." Check online for discount rates, deals, etc. If you guys want to go on a date, have the coupon ready and present it at the end of dinner, any sooner and it'll spoil the evening. When the check is plopped down, he'll be too full to argue, and might even appreciate the gesture. He shouldn't get pissed about it, if he does he's kind of a tool. Deflect by telling him that things aren't going so great financially for you either, this should motivate him to work harder. If it doesn't, then he's definitely a tool. DO NOT try getting him a job where you work! EVER! Encourage him to consider other areas of employment, but make sure they're far as fuck from where you work. You need space in a relationship. Relish it. If all else fails, dump the tool and give me a call. I'm always happy to be a kept man.