Sylvester Stallone has admitted that seeing his eldest daughter, Sophia, embark on a new chapter with her engagement is "hard," despite his strong approval of her fiancé, Michael Sheehan. Speaking to Jimmy Fallon on Sunday night, the actor reflected on the family milestone and shared a humorous anecdote about once dressing as Rambo to scare off a boyfriend at another father’s request.

"It's hard for me to say it because it's time to have a new life of her own," Sylvester said of Sophia. "But she found a great man, great fiancé, Michael." Sophia, 30, announced her engagement to Michael Sheehan in August, sharing photographs of the proposal on Instagram.

Jimmy Fallon acknowledged the daunting prospect of dating the daughter of a Hollywood action star. "It is. It is tough," Sylvester agreed, before reassuring Fallon that Michael had made an excellent impression. "I like him very, very much," he stated. "I think he's a stand-up guy. Great. Good-looking, got everything going."

The conversation offered a glimpse into Sylvester's adjustment to his daughter's engagement, balancing his feelings about her growing independence with his enthusiasm for her future husband. Sophia is the eldest of his three daughters with wife Jennifer Flavin, alongside Sistine and Scarlet, whose relationships are also explored in their reality series, The Family Stallone.

Michael's warm reception prompted Sylvester to recall a very different encounter. Without naming names, the actor explained that a famous father had asked him to intervene with his daughter's boyfriend. "So I went home, got my Rambo outfit, headband, fake blood," Sylvester told Jimmy, adding that the costume also included a knife and an ammunition belt.

Dressed as his iconic action character, he then answered the door to the unsuspecting visitor. Sylvester described the boyfriend as a "little comedian type guy" wearing his hat sideways, before demonstrating his intimidating greeting: "What do you want?" Recounting the warning he delivered in character, Sylvester continued: "If you touch her, it's like touching me." Jimmy asked if the encounter had sent the visitor away, and Sylvester indicated that it had, making it clear the boyfriend was unaware it was a prank. "I love that you did it," Jimmy responded.

Sophia's engagement announcement came on August 28, shortly after her 30th birthday. Photographs from the proposal showed the couple embracing amid candles and white roses, with other pictures offering a closer look at her engagement ring. "Forever with my best friend," she wrote alongside the announcement. Sylvester also publicly celebrated the news on Instagram, stating, "We are so ecstatic." His recent comments to Jimmy Fallon further underscored his clear affection for Michael, describing his future son-in-law simply as "a great man," despite his own intimidating reputation from playing Rocky and Rambo.