I had a few friends like that. One of them was out of work for almost a year and to keep his spirits up, I'd always shout him his dinner without making a fuss, just so he occasionally got out of the house. Then, once he gets a job as a lawyer, I fall on hard times and tell him I can't afford to go out. He gives me heaps and I end up going out but saying I'll have to keep my spending to a minimum. He has starters, main, dessert, a couple of beers and a bottle of wine then at the end of the meal (when I'm expecting he'll graciously offer to pay for the one course I had) pronounces that we'll just split the bill 50/50.
We're not in touch any more.