Dane Cook and Kelsi Taylor Relationship Timeline: Photos (2024)

Dane Cook knows his relationship with a woman 26 years his junior raises eyebrows, but he's shown a sense of humor about dating Kelsi Taylor.“Sometimes I actually find myself saying, ‘Where has she been all my life?’” Cook mused during a 2018 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.”[sendtonews type="float" key="z1OCsavm6A-2834120-14453"]The comedian opened up about the couple’s origin story during an 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 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.

Dane Cook knows his relationship with a woman 26 years his junior raises eyebrows, but he's shown a sense of humor about dating Kelsi Taylor.“Sometimes I actually find myself saying, ‘Where has she been all my life?’” Cook mused during a 2018 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.”[sendtonews type="float" key="z1OCsavm6A-2834120-14453"]The comedian opened up about the couple’s origin story during an 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 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.

“My girl @itskelsitaylor is one of my favorite people on the planet,” Cook said of Taylor on Instagram in April 2017, shortly after they started dating. “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!”

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

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.”

“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.”

“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.”

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!!!!!"

The comedian and the singer celebrated their second anniversary on May 6, 2019. “When I met Kelsi I had zero idea I was actually meeting my best friend," Cook gushed on Instagram. "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. ... I’m happier in my life & career than I’ve ever been before. Her support and love is the greatest."

Taylor, who showed off pink and red roses from the Good Luck Chuck star on Instagram Stories, also shared a sweet photo with her man to her page, writing, "You brighten up all my days and make me wanna happy dance all the time. You’re always in my heart & always on my mind. I love you and can’t wait for the years to come!"

The comedian shared a sweet message to Taylor via Instagram on his birthday. "Celebrating my day of birth with the gif of laugher & love that is @itskelsitaylor aka KTITPTB aka Little Bullet aka Baby Baby," he captioned a GIF of himself picking Taylor up as they both cheer. "These are strange times to be celebrating anything but it actually feels like a cosmic reminder we all are spinning on this watery orb surrounded by an infinity of unexplored space and a sun illuminating us as we evolve."

Cook opened up about how grateful he is for his relationship with Taylor. “I’m one of the lucky people that’s not trying to date in quarantine. Right? It’s like being in jail and having a conjugal visit. ‘I hope this goes my way, I hope I don’t get caught,’” he joked on the “On the List with Brett Gursky” podcast. “I’ve been fortunate because I’m in a really healthy relationship with somebody, both physically healthy and the relationship itself.”

The comedian continued, “We both really maintained a great kind of, like, mutual understanding that we both want to do our own independent things, but in some ways, we’re more of a robust relationship in the center because we worked on all the stuff that you should be working on also when you’re independent and then you come back to the table, it’s more time at the table and then taking that outward.”

He also noted that their relationship “has actually found a lot of growth” amid the coronavirus quarantine, but it’s still “work” at the end of the day. “It’s still always, like, a constant passing of the ball and baton and being able to remember to check-in and ‘What do you need?’ and ‘How can I help you to feel health and wellness?’” he explained. “So, all that stuff, all the boxes have been checked.”

The duo confirmed their engagement after five years together. "The secret’s out! @danecook and I are engaged," Taylor wrote via Instagram at the time. "A couple weeks ago, Dane got on one knee and asked me to be his wife and I couldn’t have asked for a more perfect moment. I love this man and love spending my life with him. I can’t wait for what’s to come." In a tweet, Cook added: "Feeling the best I’ve ever felt."

The comedian revealed that he will address the pair’s 27-year age gap in his upcoming stand-up special during an interview with E! News.

"She saw everything that I was working on for the show," he explained. "And she was like, ‘Keep that in. I think that part will be great.' There's even some fun at our own expense."

The Good Luck Chuck star added, “If we can't laugh at it, then nobody else is allowed.”

Cook and Taylor tied the knot at a private estate in Oahu, Hawaii, after six years together. “First day as Mr. and Mrs. Cook,” Taylor wrote via Instagram one day after the ceremony. “Couldn’t be more over the moon.”

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