Sounds really good! I'm glad you are doing so well!
If there's a way you could meet up with some friends for a beer and pizza or something like that, it might work...if you can keep it light and fun. But I think quiet, one on one time...that sometimes just feels so full of pressure. At least it did in my case (and really, for both of us).
With regards to his working out...if he's doing cardio, consider getting him Insanity. If he's doing weights, consider P90X. You can get these pretty cheap used (lots of people try it and give up) and you can do them right at home. If the focus is just getting healthy (and not socializing), then they are great for the money, especially if he's using a trainer and you'd like to save those dollars.
