Ione Skye's Candid Sex Confession About Matthew Perry Is Unbelievably Tragic

The world was devastated when news broke that "Friends" star Matthew Perry had died. Fans across the globe poured out their condolences, and many of his industry friends paid their respects as well — including "Say Anything" actor Ione Skye, who would later reveal that once upon a time, she had a fling with Perry that barely anyone knew about. But while their last exchange was sweet, she admitted their final in-person interactions didn't exactly go as well as she'd hoped.

Skye and Perry first met as fledgling actors in the 1988 film "A Night in the Life of Jimmy Reardon," alongside River Phoenix. While their careers ultimately took different turns, they managed to stay in touch over the years — right up until days before Perry's untimely death. In a since-deleted Instagram post, Skye shared their final text exchange, revealing a surprisingly sentimental message from Perry: "Hi! I hope all is well. I was meditating (I meditate now) and 'In [Your] Eyes' started playing. And I instantly thought of you and how beautiful you are." Skye responded with a simple, "Awe. I love that. Xo" (via People). Perry went on to wish her happiness, and sadly, just days later, he was gone.

For years, no one knew the extent of their relationship aside from the fact that they were co-stars when they were starting out. But in 2025, Skye set the record straight in her book "Say Everything," revealing they had a brief fling — one that, for her, was far from a rom-com moment. It also added a new chapter to Perry's star-studded dating history. Skye didn't go into the nitty-gritty of it all, but she made it clear that Perry's behavior left her unsettled, noting that even back then, she knew that he wasn't in a great place.

Ione Skye didn't hold back in her memoir, "Say Everything," revealing that she had a few secret Hollywood flings the public barely knew about. As it turns out, she had a relationship with Red Hot Chili Peppers frontman Anthony Kiedis, hooked up with her "Say Anything" co-star John Cusack, and had a brief fling with Matthew Perry. Before settling down with her second husband, she and Perry, who struggled with addiction, reconnected — decades after not speaking — when he invited her over for a "sober drink."

"I only had to think about it for approximately 15 seconds," Skye wrote. "I hadn't talked to Matthew since we made 'A Night in the Life of Jimmy Reardon' almost 20 years earlier, and I normally didn't accept booty calls, which I assumed this was ... but it was Matthew Perry! I was curious, and he was adorable and handsome and rich and presumably sober." But instead of the quick-witted Chandler Bing fans knew from "Friends," Skye saw the boy she'd met as a teenager. "The sex was perfectly pleasant. Though the silent talking heads on the flat-screen distracted me and Matthew seemed far away. Neither of us gave it our all," she recalled, admitting their first time wasn't "that fun." However, they gave it another shot, just in case something serious could come of it. It didn't. Perry remained "emotionally distant," and that was that.

"That was the last time I ever saw him, though for years he'd text to say hi every so often. Even through his distance, he was always endearing and sincere," she wrote, adding that she wished she'd called him to properly catch up. Instead, their story ended with that brief text exchange — one she'll always treasure.