I can't see how cleverly avoiding or spinning those type questions makes the problem better or go away. Answering like a politician ...a non answer, misdirection, spin does in effect answer the question. "I don't like questions like that...it upsets me" ... response... "WHY" ...why would that simple question upset you? Outside of the fact you don't want to hurt my feelings ...why ? See how this could slide.
Lets say you can say all the words right ....phrase it perfectly ...spin it beautifully ...the energy and body language...your eyes can all give the opposite message. Which could in fact cause other problems revolving around honesty in words ....basic trust issues.
The idea he's being fed something from an outside source seems like a huge leap not knowing him, his history, and friends and family. Also lets not forget HE'S NOT enough ...he doesn't need an additional third party to tell him that.... she's been telling him that twice a week and on some weekend's ...for how long? ...a year or 2?