You have to remember, Jack, that he's going home to your boyfriend. The more bruised and battered he is, the more sympathy he'll get. He may be invested in working this out but that doesn't mean he won't put himself first when it really counts.
"You're both terrible at this." He did talk to Ianto yesterday and gave him a similar speech to this one. "It'll take time. Chances are he doesn't know what you can do because he doesn't feel like he deserves the help."