From her days as a child star on “Who’s the Boss?” to her iconic turn as Phoebe Halliwell on “Charmed,” Alyssa Milano has been a familiar face on television for decades. But while audiences grew up with her on-screen, Milano’s real-life journey – especially in love and relationships – has unfolded with less fanfare and far more complexity than any TV script.
Milano first found fame as a teenager, but life in the Hollywood spotlight brought its own set of challenges. She learned early on that living in the public eye meant every relationship, every date, and every heartbreak could become tabloid fodder. Through it all, she remained unapologetically herself, becoming not just an actress but an activist and outspoken leader, most notably as a driving force behind the #MeToo movement.
Finding Her Match
Today, Milano’s romantic life is less about gossip columns and more about enduring partnership. She’s been married to talent agent Dave Bugliari since 2009, and by all accounts, their relationship is rooted in mutual respect and a shared sense of humor. They met in the mid-2000s through friends in the entertainment industry – a world they both understood but managed to keep separate from their private life. Their wedding, on Bugliari’s family property, was heartfelt and intimate, and now, after more than a decade of marriage and two kids, they’ve weathered the usual ups and downs of family and fame.
Milano’s path to stability, though, wasn’t quick or easy. In her twenties and thirties, romance came with its fair share of lessons. She was briefly married to musician Cinjun Tate in 1999, but the marriage ended after less than a year. There were headline-making relationships with Major League Baseball players Brad Penny, Barry Zito, and Carl Pavano – affairs that, in hindsight, Milano speaks about with a mix of candor and humor. “It was a phase where I thought maybe an athlete would understand my crazy schedule,” she once joked, adding that ultimately, love can’t be scheduled.
Alongside the famous names were plenty of rumors, from musicians to fellow actors. Milano never shied away from acknowledging her high-profile dating life, but she always drew a line between what was public and what was personal. “Lasting love isn’t about perfection – it’s about finding someone who’s willing to work through the hard parts,” she told an interviewer a decade ago, a quote that’s only gained meaning as her marriage has endured.
Growing Up, Growing Together
In many ways, Milano’s perspective on love has matured alongside her career. She’s open about the mistakes and messiness of her twenties, how the whirlwind of Hollywood can make it easy to conflate excitement with real connection. Now, she puts more value on partnership – having someone in her corner when parenting is hard or activism becomes exhausting.
Despite the attention on her public outspokenness, especially in recent years, those closest to her say her home life is strikingly ordinary. Milano and Bugliari go to kids’ soccer games, argue over dinner plans, and make time for quiet moments out of the spotlight. Friends describe them as a team, with a sense of normalcy that’s rare in show business.
Past Relationships
Dave Bugliari
Brad Penny
Barry Zito
Carl Pavano
Eric Dane
Fred Durst
Justin Timberlake
Josh Shambaugh
Brian Krause
Greg Vaughan
Jason Behr
Cinjun Tate
Eric Nies
Scott Wolf
David Arquette
Wayne McBean
Corey Haim
Corey Feldman
Kirk Cameron
It’s a far cry from Phoebe Halliwell’s supernatural love dramas, but for Milano, real life has brought something a little slower, a little less magical, and much more meaningful. Her story, at its heart, is about growing up and figuring out what really matters – both in Hollywood and at home.
