Comedian Rosie O'Donnell revealed in a Facebook Watch conversation Wednesday that...

Comedian Rosie O'Donnell revealed in a Facebook Watch conversation Wednesday that she dated a man before coming out as a lesbian. Credit: Invision / AP / Greg Allen

In a conversation about the delicate balance of coming out to one's family as gay, comedian and LGBTQ activist Rosie O'Donnell recalled her own issues with doing so, and revealed that she had dated a man at one point.

On the Wednesday edition of music star Gloria Estefan's Facebook Watch discussion show "Red Table Talk: The Estefans," the singer's 25-year-old gay daughter Emily expressed regret over not having told her late grandmother, due to Gloria Estefan saying the revelation might harm the old-world woman.

Speaking via remote video, the Commack born-and-raised O'Donnell, 58 — a family friend who has known Emily since the girl's early childhood — said she herself had faced a similar situation. "When I told my older brother I was gay," O'Donnell, recalled, "he told me, 'Don't tell dad — he could have a heart attack and it would kill him.' "

O'Donnell — whose brother, state Assem. Daniel O'Donnell (D-Manhattan), also is gay — then spoke of her own regret for hiding her relationship with Kelli Carpenter, her partner from 1998 to 2007.

"My publicist, she was like a surrogate mother to me," the comic said, referring to the late Lois Smith, who represented O'Donnell from 1996 to 2001. "She would say to me, 'Don't sit next to Kelli [at public events],' so that nobody could tell we were together and a couple. And every time she did it, it hurt my feelings. And every time I told her, she said, 'You're paying me to protect you, and I'm protecting you.' " O'Donnell came out publicly in February 2002 during a cancer-benefit performance at the comedy club Caroline’s on Broadway.

O'Donnell told Emily that long prior, "Right before I met your mom, I dated a man for two years — a lovely, lovely, warm man. But I would find myself staying in the bathroom, popping pimples, doing anything not to get to bed. Even though when I got to bed, we had a wonderful — it wasn't the sex that was the problem, necessarily, it was the emotional connection."

Top Stories