Jessica Simpson and Dane Cook had rumors swirling that they were dating in 2006, although they never confirmed the relationship. Jessica was 26 while Dane was 30.
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Racquel Houghton was 28 when she ended her relationship with Dane, which lasted on and off for over five years. He was 37.
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He was then spotted out with Nicole Scherzinger, leading to rumors that the two were hooking up. He was 39 at the time.
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Nicole was a bit more age-appropriate at 33.
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Julianne Hough was photographed multiple times on dates with Dane in 2010. She was 22.
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He was 38.
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Amanda Cerny dated Dane from 2011 to 2014, starting the relationship when she was just 20 years old. He was 39.
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His latest girlfriend is aspiring singer Kelsi Taylor. They were recently spotted kissing and frolicking in Hawaii, and Dane isn’t shy about showing her off on social media. She is 19 years old while Dane is 45.
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