Dane Cook and Kelsi Taylor’s Relationship Timeline: From Dating a Teen to Marrying His ‘Best Friend’

Dane Cook‘s marriage to Kelsi Taylor was meant to be, even though the Good Luck Chuck star has taken a lot of ribbing over the years about their 26-year age gap. The couple began dating when she was in her late teens and six years later they tied the knot in an intimate Hawaiian ceremony on September 23, 2023. Their relationship timeline shows how Dane and Kelsi have been wildly in love since meeting and their adoration has never wavered. There’s a good reason why Dane has gushed on numerous occasions that she’s his “best friend.”

Scroll down to see Dane and Kelsi’s full dating timeline.

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April 2017

Dane announced the couple’s romance in an Instagram post where he told fans, “My girl @itskelsitaylor is one of my favorite people on the planet,” adding, “She’s a talented singer but more importantly she’s a genuine person. Check out her music and get to know her. She’s gonna go far!”

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2018

During an appearance on Jimmy Kimmel Live! , Dane roasted himself about the couple’s age difference, joking, “Sometimes I actually find myself saying, ‘Where has she been all my life?’ 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.’”

Dane then gushed about his girlfriend, saying, “Here’s the thing: I love her. She is the kindest, sweetest, just my favorite — my best friend.”

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March 2019

Dane shared a loving birthday tribute to Kelsi, posting a photo of the couple on vacation and writing in the caption, “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… I couldn’t imagine a world without you!”

He continued, “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. You don’t really care about birthdays so I’ll just hold all the excitement for ya! I love you, I hope you have a day as special as you are. Let’s eat some cake!!!!!”

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May 2019

On their second dating anniversary, Dane told fans how much Kelsi meant to him, writing a post next to a black and white Hawaiian vacation photo, “When I met Kelsi I had zero idea I was actually meeting my best friend. I’ve never felt so loved & I’ve never been able to give the amount of love that I can with her. This is a special relationship and she is a special human being and she makes me feel special too. That’s not always easy for me to feel because I’m wired to compete and to reestablish, reassemble & reboot – that can leave you feeling partially complete or mostly not.”

“That all went away with Kelsi. I’m happier in my life & career than I’ve ever been before. Her support and love is the greatest. Happy 2 years baby-baby. You’re one of a kind. I’m grateful to have you as my gf and to see you smile a lot. I can’t wait to see what we do next,” Dane added.

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December 2020

Next to a Christmas Day selfie of the duo, Dane wrote, “Merry Christmas from @itskelsitaylor and I. KT and I didn’t get to see each other for weeks once she got sick. Thankful to have had another xmas together.”

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November 2021

“I love you @danecook. We’re heading into our 5th Thanksgiving together and ooooooh I’m grateful. Also putting up the Christmas tree tonight – who else is team tree before Thanksgiving?! ” Kelsi captioned this cute selfie of the couple.

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August 2022

One month after proposing to Kelsi, Dane gushed about their romance in an Instagram post next to a professional photo taken by his sister Courtney Cook. In the caption he wrote, “My sister @courtneycookimagery took this photograph of my beautiful fiancée @itskelsitaylor throwing me that smile I adore. We’ve spent the last month basking in this moment, soaking up all the goodwill and love as we plan our future together. Her kindness and strength are unmatched, Kelsi radiates a light you just want to be around.”

“Life is a hard road often, it can throw so much at you all at once – even during the moments of enjoying blessings you can find yourself alone and lost… but not anymore, not for us,” Dane added along with the hashtags, “happy couple” and “engaged life.”

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May 2023

When celebrating six years together as a couple, Kelsi wrote to Dane in the caption of this photo, “Happy happy anniversary, my love! Year 6 – this is going to be our best year yet. The year we get married! So beyond excited to be your wife. Our worlds colliding was the greatest gift. I can’t wait for what’s next for us + the life we are building together.”

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September 2023

Kelsi and Dane shared various professional photos from their wedding, with captions including, “The Cooks – 9.23.23,” and “Walking into the rest of my life with @danecook.” The couple wed at a private resort in Oahu, Hawaii, in front of 20 close friends and relatives.