Matthew Perry’s ‘emotionally distant’ sex sessions with ‘Say Anything’ star Ione Skye detailed in her new book

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Ione Skye Opens Up About a Brief, Unexpected Romance with Matthew Perry in Her New Memoir

Actress Ione Skye, best known for her roles in iconic films like Say Anything and River’s Edge, has shared a candid and intriguing story about a fleeting romance with Friends star Matthew Perry in her newly released memoir, Say Everything. The book offers a deeply personal glimpse into Skye’s life, including her experiences in Hollywood and her encounters with some of its most recognizable stars. In one particularly surprising revelation, Skye details a brief but memorable connection with Perry, a relationship that unfolded over two decades after their initial meeting.

The story begins in 1986, when Skye and Perry first crossed paths on the set of the teen comedy A Night in the Life of Jimmy Reardon. At the time, both were newcomers to the industry; it was Perry’s first film, while Skye was already gaining attention for her roles in River’s Edge and other early projects. Despite their shared inexperience, Skye admits she wasn’t immediately drawn to Perry. Instead, her attention was captured by the film’s star, River Phoenix, with whom she shared a romantic kissing scene. As Skye writes, “River was still dating Martha Plimpton, so we never kissed off camera, as much as I’d have liked to.”

A Reconnection Years Later

Fast-forward nearly two decades, and Skye found herself single and at a crossroads in her personal life. It was during this time that Perry reached out to her “out of the blue,” inviting her over for a “sober drink.” Skye recounts that she didn’t have to think twice about accepting the invitation—largely because it was Matthew Perry. While she assumed the evening might be a casual hookup, she was intrigued by the possibility of reconnecting with someone she had known early in her career.

The evening unfolded with ease. Over bubbly water and a shared cigarette, the two caught up on old times before retreating to Perry’s bedroom to “watch a movie.” Skye describes the encounter as “perfectly pleasant,” though she notes that the connection felt somewhat distant. Perry, too, seemed emotionally detached, and neither of them fully immersed themselves in the moment. Afterward, Perry casually remarked that the experience had been “fun” and suggested they “do it again sometime.”

A Fleeting Connection

Encouraged by the possibility of a budding romance, Skye returned to Perry’s home the following week. However, the second encounter was eerily similar to the first—down to the single cigarette in the kitchen, the banter over bubbly water, and the emotionally distant sex. When Skye proposed turning their meetings into a weekly ritual, Perry responded with a quizzical look, leaving her feeling uncertain and unfulfilled. That evening would mark the last time the two saw each other in person.

Though their romance fizzled out, Perry occasionally reached out to Skye over the years with friendly texts. Their final exchange occurred just one week before Perry’s tragic death on October 28, 2023, at the age of 54, due to a ketamine overdose. Perry’s message was warm and nostalgic, mentioning how the song “In Your Eyes” by Peter Gabriel—a track famously featured in Say Anything—had made him think of her and her beauty. Skye, who had become synonymous with that song, remained silent, a decision she now regrets.

A Bittersweet Reflection on Love and Loss

Skye’s memoir paints a picture of two souls navigating the ups and downs of life, love, and fame. While her romance with Perry was brief and lacked the depth she had once hoped for, it serves as a reminder of the unpredictability of human connections. Skye’s story also highlights the complexities of Perry’s life, a man who charmed millions with his wit and talent but struggled with his own demons. Her account of their relationship is both a tribute to Perry’s memory and a poignant reflection on the fragility of life and the importance of cherishing moments with loved ones.

In sharing her story, Skye invites readers to reflect on their own experiences with love, loss, and regret. Her memoir is not just a celebrity tell-all but a deeply human exploration of the moments that shape us—and the ones that slip away.

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