Dane Cook and Girlfriend Kelsi Taylor's Relationship Timeline

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Dane Cook knows his relationship with a woman 26 years his junior raises eyebrows, but the 46-year-old shows a healthy sense of humor about dating 20-year-old Kelsi Taylor.

“Sometimes I actually find myself saying, ‘Where has she been all my life?’” the Good Luck Chuck star mused during a recent appearance on Jimmy Kimmel Live! “And then I realize she wasn’t alive for the first 26 years of it.”

He continued: “People are like, ‘You’re robbing the cradle.’ I was like, ‘She hasn’t slept in the cradle for like nine years. Relax.’”

All jokes aside, Cook praised the singer-songwriter, whom he’s been dating since 2017. “Here’s the thing: I love her,” he told Jimmy Kimmel. “She is the kindest, sweetest, just my favorite — my best friend.”

The comedian opened up about the couple’s origin story during August 2018 Instagram Stories Q&A, revealing that he met Taylor at a game night he hosted at his home. After staying friends “for a while,” the duo soon “fell in like with each [other] and then upgraded to love,” Cook told followers.

When asked for advice on dating despite an age gap, he joked, “The only thing you have to do is plan that your deaths will be somewhat far apart.”

And when an Instagram user asked the comic about his and Taylor’s favorite aspects of one another, he replied, “Kelsi is smart, kind, creative, loyal & honest. As for me, I think Kelsi would [say] I’m tolerable. LOL.”

That Q&A wasn’t the only time Cook waxed romantic over his girlfriend via Instagram. “We’ve already made amazing memories & I can’t wait to see what’s next,” he wrote in one recent upload. “Well, besides us binge watching every season of Game of Thrones all over again before the new season.”

Scroll through the relationship timeline below to see loving posts of his and other details from their relationship.

March 2019

The “Longing” singer wished her significant other a happy birthday on Instagram on March 18, 2019. “Happy birthday lover. Your bright, happy face, brain that never stops working, never ending energy, jokes that bring out my annoying laugh, determination that keeps me inspired, heart that just has a way of melting mine,” she wrote. “I couldn’t imagine a world without you! You’re so important to me and I can’t wait for all the other birthdays we will spend together. Thanks for being my ride or die. … ! I love you, I hope you have a day as special as you are. Let’s eat some cake!!!!!”

Courtesy Kelsi Taylor/Instagram

January 2019

“Dane is so in love with Kelsi,” a source exclusively told Us Weekly in January 2019, shortly before the couple were spotted packing on the PDA on a Hawaiian beach. “He treats her as though she’s his wife even though he’s said he’ll never get married. … This is definitely the most serious relationship he’s had so far.”

Courtesy of Kelsi Taylor/Instagram

February 2018

“I can’t say enough good stuff about this incredible woman,” Cook said of Taylor as he uploaded this selfie on Valentine’s Day 2019. “I’m a lucky sap to have her by my side. I like this pic because it captures how happy we are.”

Courtesy of Dane Cook/Instagram

February 2018

When the American Gods actor mentioned the pair’s 26-year age gap during his February 2018 Jimmy Kimmel Live! appearance, he noticed an audible reaction from the audience. “Thank you for the snickers of approval,” Cook told the crowd. “I’m sure that wasn’t judgment at all.”

ABC/Randy Holmes

January 2018

Just after captioning this selfie with the hashtag “#relationshipgoals” in January 2018, Cook posted another Instagram tribute, calling Taylor “simply a gift.”

Courtesy of Dane Cook/Instagram