If you burn more calories than you eat, you lose weight. If you eat more calories than you burn, you gain weight. I know, this isn't news.  The key to him gaining weight is to eat more!
I was in a similar situation - I dropped to about 20lbs below my ideal weight. What helped me was quick breads (banana bread, pumpkin, zucchini, etc) and muffins - higher in calories without feeling quite so much like "junk food" like cake would - and, believe it or not, potatoes. I learned early on that if I cut up potatoes into something like oven fries, I can easily eat 3 large potatoes' worth in one sitting... and I'm not a big girl! I always recommend finding something safe that he finds irresistable, and making sure you ALWAYS have it around for munching.
Safe protein shakes - SpiruTein is the best - might also be a good idea. The same thing could really be accomplished with a good smoothie, though - some peaches, a frozen banana, a little honey or sugar, and some soy milk, in the blender. The idea is to replace water he's drinking with something that has calories... that will help too.
Good luck! Gaining weight is definitely possible - I put on 20lbs in a couple months! LOL 
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It's all about calories!
