Eric Dane and Alyssa Milano had a brief romance that turned into a decades-long friendship. Dane and Milano dated in the early 2000s before he landed a role on Charmed, which starred Milano, Holly Marie Combs and Rose McGowan. After splitting up, Dane went on to marry wife Rebecca Gayheart in October 2004. Milano, for her part, wed husband David Bugliari in August 2009. Following their split, Dane and Milano remained cordial over the years. In April 2025, Dane revealed he was diagnosed with ALS. The Grey's Anatomy alum died the following year at age 53. "With heavy hearts, we share that Eric Dane passed on Thursday afternoon following a courageous battle with ALS. He spent his final days surrounded by dear friends, his devoted wife and his two beautiful daughters, Billie and Georgia, who were the center of his world," a statement from the Dane family read. "Throughout his journey with ALS, Eric became a passionate advocate for awareness and research, determined to make a difference for others facing the same fight. He will be deeply missed and lovingly remembered always." After news broke of Dane's death in February 2026, Milano paid tribute to her late friend. "I can't stop seeing that spark in Eric's eye right before he'd say something that would either make you spit out your drink or rethink your entire perspective," she wrote via Instagram at the time. "He had a razor-sharp sense of humor. He loved the absurdity of things. He loved catching people off guard." Keep scrolling for a look inside Dane and Milano's friendship over the years: 2000s Alyssa Milano and Eric Dane dated in the early 2000s. The pair enjoyed a night out at the 2003 premiere for the movie Dickie Roberts: Former Child Star. 2003-2004 Eric Dane joined the cast of Charmed in season 5. Dane played Jason Dean, who was a love interest for Milano's character Phoebe Halliwell. Dane was on the WB series for two seasons. 2024 During a July 2024 episode of Dax Shepard's "Armchair Expert" podcast, Eric Dane opened up about his past romance with Alyssa Milano. "I had a massive crush on Alyssa when I was 14. By the time I was 28, and we were dating, I wasn't a child anymore and she was a person. A lovely wonderful person," he recalled. "We dated for a little bit and she was obviously doing the show Charmed. She asked me if I wanted to be on it. I think I ended up doing like 10 episodes." Dane joked that his role was limited because they "broke up" in real life. 2026 After news broke of Eric Dane's death, Alyssa Milano sent her condolences to his family in a touching tribute. "When it came to his daughters and Rebecca, everything in him softened. He carried them with him even in rooms where they weren't present," she wrote via Instagram. "You could see it in the way his voice changed when he said their names. A breathtakingly beautiful family." Milano also looked back fondly on her memories with Dane. "The spark. The mischief. The tenderness he kept guarded but never totally hidden," she continued. "He convinced me to get my pixie cut and my nose piercing. He also was with me on the walk when we found Lucy, my beloved rescue chihuahua. He called me "Milano," as if it was the only part of my name that mattered. My heart is with the people who were lucky enough to be his home."