"She was unbelievably cool, shockingly cool" when he first told her he was pursuing it, he said. "But as time went on and the reality started to set in, I felt her pulling away from me a little bit. And then when my voice started to change," after he began receiving testosterone shots, "is when it really hit her."
A counseling session ended badly. "The hard thing for my mom, I think, is because she's a public figure and because she has this personality of being so cool about stuff and progressive, people forget that she's a parent."
Winfrey used the interview as an opportunity to promote the documentary "Becoming Chaz," airing Tuesday on Winfrey's cable channel, OWN.