Sounds like T is really a good one! I really like the boat example. I wish The X and I had found your T instead of the disaster of a traditional MC we went to!
As for the ring - why not decide to give your H till the end of February. If he is still ringless - maybe ask him then. Work with the T and see what he/she thinks.
I don't want to offer false hope - but Valentine's Day is coming up - maybe he wants to make an occasion of it when he puts the ring back on.