'Who's the Boss?' actor Danny Pintauro reveals 'iffy' relationship with co-star Alyssa Milano

August 2024 · 2 minute read

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Despite forming tight-knit relationships on the set of the 1980s classic “Who’s the Boss?” Danny Pintauro has revealed there was one castmate with whom he struggled: Alyssa Milano.

Pintauro — who played Jonathan Bower on the hit sitcom, which ran from 1984 to 1992 — reminisced about his time on the show, admitting he had “iffy moments” with Milano, who played Samantha Micelli.

“It couldn’t have been a better experience. We really did come together as a family,” the 46-year-old said on David Yontef’s podcast, “Behind the Velvet Rope.”

However, he chalked up differences with Milano to their sibling dynamic.

“We did Christmas gifts. I got Judith Light ‘Merry Christmas, Mom’ stuff, and I got Katherine Helmond grandma stuff,” he reminisced. “I loved being there, but Alyssa and I had iffy moments — that was really because she was a teenager, and I was the younger brother.

“She was like, ‘Get out of here!’ and slammed the door in my face,” he continued. “There was no malice to it — just older sister/younger brother things.”

Characters played by Danny Pintauro and Alyssa Milano annoy each other in a scene from “Who’s the Boss?” ©Columbia Tristar/Courtesy Everett Collection
Alyssa Milano, Katherine Helmond, Tony Danza, Judith Light, and Danny Pintauro are shown in a Season 6 promotional photo for “Who’s the Boss?” ©Columbia Pictures/Courtesy Everett Collection
Danny Pintauro said he and Alyssa Milano were not close for years during and after filming the sitcom “Who’s the Boss?” Getty Images

Pintauro admitted he kept in touch with Milano, 50, the least out of all the cast for about a decade after the show ended, saying they “never developed that sort of bond.” But their relationship shifted when found out that he came out as HIV positive.

“She was totally caught off guard,” he said, noting that she had a “bit of a teary moment” while on “The View” after the news emerged.

“Right after that episode, I got a text from her, and our relationship developed a lot more,” he told Yontef.

“Who’s the Boss?” cast members Judith Light, Danny Pintauro, Tony Danza, Alyssa Milano, and Katherine Helmond are shown in 1984. ©Columbia Pictures/Courtesy Everett Collection

Pintauro recently returned to acting after a 30-year break, appearing in a Lifetime Christmas movie, “A Country Christmas Harmony.”

The Post has reached out for comment from representatives for contacted Milano.

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