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“I Cried Every Single Day For Half A Year”: Val Kilmer’s Memoir Dating Confessions Resurface
Val Kilmer, who once described women as “butterflies” and men as “big oafy elephants,” had a dating history with as much drama, passion, and heartbreak as his blockbuster movies.
From Cindy Crawford to Angelina Jolie, he dated numerous Hollywood starlets. He was also one of the few men to break the heart of Cher, who was about 14 years older than him.
Highlights
- Val Kilmer has dated a string of Hollywood stars since the 80s.
- He once revealed that there was one actress who left him heartbroken and crying for 6 months.
- Cher described him as one of the few men who broke his heart.
- Despite a long dating history, Kilmer said he experienced loneliness over the last couple of decades before his passing.
But the late actor revealed in his memoir that there was one actress who left him shattered and crying “every single day for half a year.”
“I’ve always found women infinitely more interesting than men,” the Top Gun star wrote in his 2020 memoir I’m Your Huckleberry. “Perhaps that’s why we’ve always gotten along.”
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Despite dating some of the most iconic women in Hollywood, Val Kilmer admitted to struggling with loneliness
Image credits: Terje Oegema
Kilmer succumbed to pneumonia on April 1 at the age of 65.
Prior to his passing, he revealed that he struggled with loneliness despite his romances with multiple Hollywood starlets.
“I haven’t had a girlfriend in 20 years. The truth is I am lonely part of every day,” he wrote in his memoir.
Kilmer’s dating history with famous women goes all the way back to the 80s, when he met Cher at a birthday party fresh out of Julliard School.
Cher described Val as someone unlike anybody she’s ever known but said their age gap was “a bigger deal back then.”
Cher admitted he was one of the few men to break her heart
Image credits: Barry King/WireImage
Their relationship went from friendship to “madly in love and laughing hysterically” to “respecting each other’s ability,” Cher told People in 2024.
The Believe singer admitted he was one of the “few” men to ever have broken her heart.
“I was madly in love with Val Kilmer and he left,” she told Howard Stern’s SiriusXM.
Image credits: cher
“He’s like nobody I’ve ever known,” she told People in 2021. “He is exasperating and hysterical. Thrilling and funny, and doesn’t do what anyone else does.”
“And he was so beautiful. It went from madly in love and laughing hysterically to respecting each other’s ability.”
Reflecting on how she was 36 and Val was 23 when they were dating, she argued that younger men weren’t “intimidated” by her.
Val fondly wrote about Cher in his memoir and said she was a pillar of support for him to lean on when he was diagnosed with throat cancer in 2014.
“Once Cher works her way inside your head and heart, she never leaves. For her true friends, her steadfast love and loyalty never die,” he wrote.
Kilmer said there was a “secret pain” about his connection with Michelle Pfeiffer
Image credits: ©ABC/Courtesy Everett Collection/ Vida Press
Kilmer was briefly linked with Michelle Pfeiffer after they met on the set of One Too Many. They became friends, with the actress being comfortable enough to confide in him about her tumultuous marriage with Peter Horton, whom she eventually divorced.
Not much is known about Kilmer’s romance with Pfeiffer, but it is believed they briefly dated in the 1980s.
“The secret pain that Michelle and I shared created an intimacy between us,” The Doors actor wrote in his memoir.
Ellen Barkin was “one of the enchantresses who got away”
Image credits: Vinnie Zuffante/Getty Images
Decades after his romance with Ellen Barkin, Kilmer still remembered her “wit,” her “sultry eyes,” and her laugh.”
She had “the best smile in all five boroughs,” he penned in I’m Your Huckleberry.
The pair used to enjoy window-shopping on Rodeo Drive by day and barbecuing at night. But Barkin eventually became “one of the enchantresses who got away.”
Kilmer was convinced his “unmanageable preoccupations” and “neglect” were the reasons for their split.
The legendary actor admitted he fell madly and hopelessly in love with Carly Simon
Image credits: Ron Galella, Ltd./Ron Galella Collection
During the New York premiere of Top Gun in 1986, Val crossed paths with Carly Simon and went on to fall “madly, hopelessly in love with her.”
“I’m not sure I ever spoke those words, but you must have known, Carly,” he wrote.
A week after the Top Gun premiere in NYC, he said he paid her a visit at her Upper West side home, and they talked about “everything under the sun.”
“She had utter power over me,” he said. But things did not work out, and Kilmer believed it was because she realized it was “too overwhelming” for him.
Kilmer found out about his divorce with Joanne Whalle while watching CNN in a hotel room
Image credits: Ron Galella, Ltd./Ron Galella Collection
The one and only woman that Kilmer walked down the aisle for was Joanne Whalley, whom he met on the set of George Lucas’s fantasy epic Willow (1988).
After tying the knot in 1988, they became parents to daughter Mercedes, 33, and son Jack, 29.
Kilmer once told Tampa Bay Times that he found out Whalley was divorcing him due to “irreconciliable differences” while watching CNN in a hotel room.
“It was no fun,” he told the outlet in 1999.
Cindy Crawford helped him find love again after his divorce
Image credits: Georges DeKeerle/Sygma
Following his divorce, Kilmer credited Cindy Crawford for helping him find happiness and love.
He described her as “smart” and a “fantastic cook” with a “great sense of humor.”
The Birthday Cake actor gushed with praise for her during a Good Morning America interview in 2020.
“Oh God, I loved Cindy and just kept loving her, I thought I could have died from her love because its delight was simply too much to bear. I would die of happiness,” he said.
Kilmer dated Jaycee Gossett for a couple of years and called her his “best friend” at the time
Image credits: Ron Galella, Ltd./Ron Galella Collection
When his two-year romance with Crawford came to an end, Kilmer found his way to Jaycee Gossett, whom he dated between 1988 and 2000.
He said she was his “best friend” at the time and had visited the White House with her in 2018.
Kilmer’s breakup with Daryl Hannah left him crying every single day for six months
Image credits: Frank Trapper/Corbis
Perhaps the most heartbreaking romance for Kilmer was the one he shared with Daryl Hannah, whom he dated briefly in 2001.
While writing his memoir, he said he was “still in love with Daryl,” and their breakup was “by far the most painful of all.”
He said he was sure he would love her “with [his] whole heart forever” and that his love for her had “lost none of its strength” when he wrote his memoir.
“When we finally broke up, I cried every single day for half a year,” he penned.
The Top Gun star wrote about having a “tragic” and “soulful” fling with co-star Angelina Jolie
Image credits: SGranitz/WireImage
Among some of the flings he had, Kilmer also had a brief something-something with his Alexander co-star Angelina Jolie.
“[I] couldn’t wait to kiss her,” he wrote about their time together on set.
During their “tragic” and “soulful” fling, he said Jolie was the “angel” who “recused [him] from an icy inferno of solitude.”
“Perhaps the most soulful and serious of them all,” Jolie was “more gorgeous, more wise, more tragic, more magic, more grounded,” he wrote.
Fans shared their grief over Val Kilmer‘s passing this week
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