Matthew Perry’s dating history contained a mixture of celebrities and normal women, but he and Dunn shared a special bond. Their relationship spanned from 2003 to 2005; however, it’s clear Perry still held a special place in his heart for his one-time love. Although Perry was never engaged or married to Dunn, he once came super close to popping the question. “The relationship had deepened to the point where there was now a question, I urgently needed to ask her,” Perry recalled in his 2022 memoir, “Friends, Lovers, and the Big, Terrible Thing” (via Us Weekly). “One day, I said, ‘I think we should stop kidding ourselves. We love each other,’ and she didn’t disagree.”
Unfortunately, Perry never scrounged up the courage to ask for Dunn’s hand in marriage. “I often think if I’d asked, now we’d have two kids and a house with no view, who knows — I wouldn’t need the view, because I’d have her to look at; the kids, too,” said Perry. “Instead, I’m some schmuck who’s alone in his house at 53, looking down at an unquiet ocean.” Based on his writings, it seems that Perry never truly got over Dunn, despite embarking on several more relationships in subsequent years. The extent of Perry’s communication with Dunn before his death is unknown. As for Hurwitz, fans will probably never know why Perry didn’t feel a need to update his will and include her in the mix.
