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Celebrity kids often date within the same circles. From Patrick Schwarzenegger and Miley Cyrus to Brooklyn Beckham and Nicola Peltz, these pairings are usually hardly news. Steven R. McQueen and Sean Penn’s daughter Dylan Penn dated for a while before moving on with other people.

Steven R. McQueen and Dylan Penn had a brief fling

Dylan Penn attends the 2022 Brooklyn Film Festival Opening Night
Model and actor Dylan Penn in 2022 | Arturo Holmes/Getty Images

News broke in 2014 that McQueen was dating Dylan Penn, the daughter of actor Sean Penn. The pair attended Sean’s Help Haiti Home Gala where the actor was also seen cozying up to Charlize Theron.

US Weekly reported that Dylan and McQueen packed on the PDA at the event and even posed for a few photos together. When asked about her relationship status, Dylan played coy, stating she was single. Her mother, Robin Wright, said her daughter was “singly happy.”

Despite Dylan’s denial of a relationship with McQueen, the publication wrote that Steve McQueen‘s grandson was the ultimate gentleman at the party, reportedly picking her up, kissing her, and carrying the model out of the party when she complained that her feet hurt.

The couple kept their romance a secret, but a source close to them said they’d been dating for some time. The source revealed that Dylan and Steven had “met a while back.” They started dating pretty quickly. Lots of attraction there,” the source said.

They continued, “Dylan [Penn] is a fun chick. Whatever she had with Patterson was very brief, if at all. Steven had met Sean before the event last night.” The source further revealed that Sean wanted what was best for his daughter, and “whatever makes her happy is fine with him.”

Dylan Penn and Steven R. McQueen broke up months later

Two months after the pair became official, they called it quits, ending their brief relationship. A source told E! News that there were no hard feelings between the model and Steven, saying, “I think it just fizzled out.”

Dylan had previously been linked to Twilight star Robert Pattinson. But in an interview with GQ, the model revealed that all the rumors were “bulls–t,” saying they were “actually kind of funny.”

Rumors about the two surfaced in 2013 when they were spotted at Chateau Marmont and attended a private book party a month later. While Dylan refuted the claims of a hookup with Pattinson, sources revealed the two dated.

Steven and Dylan moved on with other people


‘The Vampire Diaries’: Why Did Steven R. McQueen Leave the Show?

After his relationship with Dylan, Steven moved on with Olivia Pickren. The two dated for two years from 2014 before calling it quits in 2016. He announced in 2018 that he was engaged to model Alexandra Silva with a black and white picture captioned “She said yes.” The duo called off their engagement months later, in May 2018.

Not much is known about Dylan’s personal life. Since she and Steven went their separate ways in 2014, the star’s career has taken precedent even in tabloids with news about whom she is cozying up to being nonexistent.

Steven has been busy with back-to-back projects, having appeared in The Vampire Diaries throughout its entirety and moving to One Chicago in 2015. He appeared in Chicago Fire in 2015 and 2016 before moving to Chicago P.D. in 2016. He also had a role in Legacies and a guest role in Medal of Honor.

On the other hand, Dylan has had a busy schedule, having graced covers and walked runways for major fashion labels. She had her acting debut in Condemned. She also appeared in Elvis & Nixon and costarred with her father in Flag Day in 2021.