I felt that too with some of the things my T said. ("One day you'll have to kill me off. You have to own that" while at the same time telling me he's still close to his former therapist).
Actually I think he was just insensitive, and your T's comment sounds quite similar. Like a really clumsy way of reminding us (as if we needed reminding!) that the relationship is finite and professional. Probably not intended to hurt but perhaps naïve on our Ts' part.
It's great you have another T to fall back on who already knows you. My new T is having to sort of fill in the gaps himself because I'm so keen to get on with processing the transference that I'm not giving him a chance to get to know me.