18 Dates That Were About Anything but Not Romance

Demi Moore and Ashton Kutcher’s relationship once captivated Hollywood, with its whirlwind romance, headline-making moments, and emotional ups and downs. Now, more than a decade after their split, new reflections from both Demi and those close to her are shedding light on what really led to their divorce.
The two met in 2003 at a dinner party, and despite a 15-year age gap, sparks flew quickly. By 2005, they married in a Beverly Hills home ceremony. Friends described the wedding as full of love and authenticity, a true reflection of who they were as a couple. In public, they often laughed off the age difference, even poking fun at it during an episode of Saturday Night Live.
But privately, they were navigating challenges. Moore had a miscarriage six months into her pregnancy, something she later revealed left her feeling “lost” and “empty.” The couple tried fertility treatments and explored adoption, but the emotional toll was heavy. In her 2019 memoir Inside Out, Moore shared how these personal losses and Kutcher’s alleged infidelity chipped away at their marriage.
Kutcher embraced Moore’s daughters (Rumer, Scout, and Tallulah), whom she shares with ex-husband Bruce Willis. And there seemed to be mutual respect between Kutcher and Willis, with Moore saying they approached parenting “as a team.”
By 2011, however, Moore and Kutcher announced their separation. The divorce wasn’t finalized until 2013, and both have since moved forward; Kutcher marrying Mila Kunis and Moore continuing to share her story through interviews and writing. Even years later, Kutcher reflected on that chapter of his life, admitting the divorce made him feel like “a failure,” but also expressing enduring respect for Moore and her daughters.
By 2011, the cracks in Moore and Kutcher’s marriage had deepened. That year, a 22-year-old woman came forward claiming she had an encounter with Kutcher in a Los Angeles hotel room. Moore later revealed in her memoir that she found out through a Google alert on her phone.
“I got a Google alert on my phone,” she wrote. “‘Ashton Kutcher caught cheating’ flashed across my screen. Our anniversary had just passed. There were quotes from a young blonde replaying Ashton’s pickup lines. I felt sick to my stomach: I knew those words. I knew she wasn’t lying.” Their marriage ended soon after.
Well, here’s a blast from the past: More than ten years after Demi Moore and Ashton Kutcher called it quits, Tallulah Willis, Demi’s daughter, is opening up about her ex-stepdad. In April 2025, she popped into the comment section of an Instagram post by Gwyneth Paltrow, who was talking about blended families, and Tallulah had some real talk to share.
“I have a lot to say on this! Especially how to move through an ex-step parent. No one needs to be the bad guy for a situation to be healed, there’s room for everyone,” she wrote, hinting at her relationship with Kutcher.
He shared in a 2020 interview on WTF with Marc Maron, “I was never trying to be their father... If they don’t want an engagement with me, I’m not going to force it. But they all do, and it’s great.”
Even with the challenges, Demi, Ashton, and their extended family have often shown grace and humor when speaking about their past. From Super Bowl commercials to interviews years later, there seems to be mutual respect—and a shared understanding that healing doesn’t mean picking sides.
And most recently, Tallulah’s comment reminded everyone that families—blended, broken, or somewhere in between—don’t always follow the usual script. As she put it, “there’s room for everyone.”