Jeremy Sisto Reminisces About His First Actress Girlfriend Reese Witherspoon: “I Was So Into Her”

Jeremy Sisto Reminisces About His First Girlfriend Reese Witherspoon
In his Reddit AMA, Wicked City actor Jeremy Sisto recalled his relationship with his first actress girlfriend, Reese Witherspoon. Steve Granitz/WireImage; John Shearer/Getty Images for Draper James

The cutest trip down memory lane! Wicked City actor Jeremy Sisto conducted his Reddit Ask Me Anything on Monday, Nov. 2, and revealed what it was like to date his first actress girlfriend, Reese Witherspoon.

Sisto, now 41, met Witherspoon on the 1992 TV movie drama Desperate Choices: To Save My Child. In it, a then-unknown Witherspoon, now 39, portrayed a teenage girl whose life turns upside down when when she's diagnosed with leukemia. A fan brought up the movie and Sisto's subsequent real-life relationship with the future Legally Blonde star.

"You played the boyfriend of a then-unknown Reese Witherspoon in the TV-movie Desperate Choices: To Save My Child," the AMA user wrote. "Again, what was it like working with her?"

"Great," Sisto replied. "She was my first actress girlfriend. We had a long distance relationship for a long time. I was so into her."

But, like every great romance, theirs ended — with some miscommunication. "Then she went to Africa to do a movie," he recalled of Witherspoon's 1993 film, A Far Off Place. "And i guess i thought she had broken up with me because she didnt call that much so i moved on and met my ex-wife Marisa [Ryan]. When she returned i found out that wasnt her intention but i had already gotten involved. Felt badly. She's a great person."

Though the exes cleared the air, they almost had a near reunion on the 1995 set of Clueless. The cult classic's writer-director, Amy Heckerling, shared this past summer in As If!: The Oral History of Clueless, that Alicia Silverstone faced some strong contenders for the role of Cher.

"I had my heart set on Alicia. [But] Fox . . . wanted me to explore all the [options]," Heckerling wrote. "Then they go, 'You've got to see the girl in [Flesh and Bone].' I never got to see her. I guess she was off on other things. That turned out to be Gwyneth Paltrow."

There was also Witherspoon. "I met with Reese because everyone said, 'This girl's amazing. She's going to be huge.' I saw some movie where she had a southern accent. Maybe it was on TV, a movie of the week. But I did see some scenes of hers and went, 'Wow. She's amazing.' But Alicia is Cher."

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