Fans are sending well wishes to Crystal Hefner after her dog Charlie passed away.
The 30-year-old wife of Hugh Hefner, 90, shared the sad news on Instagram, writing a touching message to her Cavalier King Charles Spaniel, which was a gift from her husband.
"Saying goodbye tonight," the model captioned a photo of her furry friend. "This is one of the hardest things I've ever done in my life. I love you more than you could ever know Charlie."
The blonde beauty previously opened up about her pup, who appeared on the July 2011 cover of Playboy, saying, "Charlie is always so happy to see me — that’s our dog’s greatest gift to us."