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Alison Pill: My Newsroom Costar Tom Sadoski Played Part in Joshua Leonard’s Proposal: Details!

Alison Pill and Joshua Leonard
Alison Pill and her new fiance Joshua Leonard attended the premiere of his new HBO series Togetherness on Jan. 6.

Leave it to Don Keefer to document the major moments! Right after the New Year, actress Alison Pill announced her engagement to actor Joshua Leonard, flashing her ring on Instagram. But behind the scenes (as always) was Pill’s Newsroom costar and on-screen ex Tom Sadoski, who played producer Don Keefer on the HBO journalism drama.

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“I had been on a rocky mountain top in Joshua Tree, and Tommy Sadoski, who is like my older brother, who plays Don [Keefer] on The Newsroom, documented with his camera the entire thing,” Pill, 29, told Us Weekly at the L.A. premiere for her fiancé’s new HBO series Togetherness on Jan. 6.

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But Pill almost didn’t make it to the proposal part. 

thomas sadowski
Tom Sadowski played producer Don Keefer on The Newsroom.

“We should also add that just before it happened Alison nearly fell off the rocky cliffside, so I ushered her over under the guise of protecting her from falling to her death,” Leonard, 39, added. 

It was then that the actor got down on one knee on a bed of rocks and popped the question. 

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“It was pretty amazing. I thought we were about to take a picture when he said, ‘Tommy let’s do this!’ I was like, ‘Alright let’s… Wha, What?!!’” Pill said. “And unbeknownst to me he had already cleared it with my parents!”

“Her family is in Canada, and we were back there over the holidays and I cornered them while she was taking the dog out for a walk,” Leonard explained. “Alison comes from a feminist household, so I figured it would be important to ask both parents’ permission, lest it seem too patriarchal, and they were both very supportive, as are my parents, so it’s very exciting.”

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Leonard picked at 1920s vintage-style ring, designed by the father of a friend. 

When asked about a possible wedding date, he laughed, replying, ”We have no idea. It’s been four days! Give us a break!” 

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