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Fox Network’s series Party of Five became a critic’s favorite when it premiered in 1994, but almost went on the chopping block due to low ratings. Thanks to winning a Golden Globe Award, and the appeal generated by some of the young male leads, the show continued for six seasons. One of those leads revealed that he was dating a co-star while on the show, after his engagement to actress Alyssa Milano ended.

Matthew Fox, Scott Wolf, Lacey Chabert, Paula Devicq and Neve Campbell | Ron Galella, Ltd./Ron Galella Collection via Getty Images

Some solid TV credentials

Actor Scott Wolf made quite an impression once he hit the screen. With his boyish good looks and easy charm, he soon became a fan favorite playing the role of Bailey Salinger on Party of Five. Wolf was part of a cast that included Matthew Fox, Neve Campbell, and Lacey Chabert, all of whom played siblings who lost their parents due to a car accident.

Wolf has also appeared in television shows including Everwood, The Nine, Spin City, and even hosted Saturday Night Live in 1998. In 2019, he was cast as Carson Drew in the CW series Nancy Drew.

Dated his brother’s on-screen girlfriend

Part of the Party of Five storyline included Wolf’s character being involved in a romantic relationship with Sarah, played by Jennifer Love Hewitt. Originally, Hewitt was only supposed to be in a few episodes, but became popular with viewers so she was kept on for several seasons. “Sarah was supposed to be in nine episodes,” Hewitt said, according to E! News. “When it got picked up, they asked me to stay on for another 13, and I thought it was only going to be 13, and then they asked me to do another season so it keeps going and going. I am so incredibly grateful for it.”

Fox played Bailey’s brother Charlie and surrogate father to the siblings, who was in an on-again, off-again relationship with Kirsten, played by Paula Devicq. While those two characters were married in the show’s final season. it was Wolf who actually dated Devicq in real life while on the series, as E! News reports.

Broken engagement

When Wolf started on Party of Five, he was engaged to actress Alyssa Milano. At the time, the two were the epitome of romantic love. “I knew it the second I met him. I called my mom and told her, ‘This is the man I’m gonna marry,’”   Milano revealed to People in a 1994 interview.

Wolf sounded just as smitten. “I could have asked her to marry me two weeks after we met. I’m convinced we’re like two halves of the same soul,” he said at the time. “It’s nice when other people notice. People get all oogily around us.”

The two met when Wolf was pursuing an acting career after graduating from George Washington University with a finance degree. They were both cast in the film Double Dragon in Cleveland, and sparks eventually flew. After filming wrapped and they both went back to California, the couple was afraid their passion would wither on the west coast. “We were both scared to death that it wouldn’t be the same here,” Milano told People. “I’ll never forget the feeling when he drove up to the house. I was so nervous I wanted to throw up.”

But Wolf said it all worked out. “We looked at each other and we knew in a second that it was going to be okay,” he said.

Soon after moving in together, Wolf proposed. At the time, it seemed as though their relationship would last forever, with Milano’s main concern being how they met. “I really don’t want people to look at this as another couple who met on a film set,” she said, afraid others wouldn’t take their relationship seriously. “This is anything but that,” Wolf reassured her. “You can interview us 25 years from now—and we’ll prove it.”

Well, not so fast. The couple soon split, but both eventually found their happy endings. Wolf went on to marry MTV’s Real World star Kelley Limp, and Milano wed CAA agent Dave Bugliari.

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