Dane Cook’s New Fiancée Was a Teen When They Started Dating and It’s Creeping People Out

Dane Cook set the internet ablaze on Tuesday for the first time in years—and it’s not his jokes that have people talking.

The 50-year-old comedian announced his engagement to Kelsi Taylor, a 23-year-old aspiring singer and Pilates instructor from Los Angeles, via a coordinated and effusive piece in People magazine.

“I was asking my best friend, the woman who I’ve shared some of the greatest times of my life with, to marry me so we can start the next chapter of our lives together. I was also thinking of how absolutely stunning she looked,” the comic said.

Taylor added: “The second he began to reach for his back pocket, my stomach flipped. I couldn’t have asked for the moment to have been more perfect. All that was going through my brain was, ‘Wait, is this actually happening right now? Is he proposing?’”

A few hours later on Instagram, he shared a video of the July 13 proposal, which took place at his vacation home in York Beach, Maine. The Massachusetts native says the town holds special significance to him, having spent a lot of his time as a child there and even scattering his mother’s ashes in the seaside village at her request.

The clip shows Taylor smiling and holding up her ring for the camera. Drone footage of the picturesque shore and throwbacks to the couple’s five-year relationship round out the celebratory post. Beyond the size of the rock or how he kept the plans under wraps, it’s their 26-year age gap that’s sparked most of the online chatter about the pair.

To be clear: Cook started dating Taylor in 2017 when she was just 18 years old.

The May-December romance, to put it generously, has kicked off quite a bit of conversation about age differences and “grooming,” that dreaded word that’s been co-opted by the right to refer to anything gay people do but that still has a specific meaning, believe it or not.

“Cut Dane Cook some slack. His only choice was to date someone too young to have heard of him,” said one person. “Chris delia and dane cook walk into a bar and their dates have to wait outside,” joked another, referring to the stand-up comedian and Whitney actor who was dropped from his agents after numerous women accused him of pursuing them online when they were underage. Cook was further compared to other adult male celebrities who have previously dated teenagers, including Jerry Seinfeld and Elvis Presley.

In 2018, Cook said that he met the songstress during a game night at his house. During an Instagram Q&A, he said they were friends “for a while” before they “fell in like with each [other] and then upgraded to love,” according to Us Weekly.

Not much is known about Taylor. Her Spotify page counts a mere 17 monthly listeners. Her latest single, 2019’s “Fall In Love,” has amassed 1,163 plays as of Tuesday afternoon. “This ain’t how you fall in love. But I don’t wanna stop because it might be time for me to drop my guard. I know you been trying so hard, but I can’t take another scar,” she sings over a lush piano arrangement with a delicate yet powerful voice.

Cook has promoted her budding career on Instagram a few times, writing in April 2017, “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!”

The comic’s star has dimmed considerably since his heyday in 2007. Things started taking off for Cook at the turn of the century, about a decade after he first started performing in 1990. A once omnipotent comedian with the power to fill arenas across the country, his younger-skewing crowd (who make up today’s elder millennials) eventually outgrew his cartoonishly energetic stage persona that was short on punchlines and high on volume. That, combined with a joke-stealing scandal that was briefly addressed on Louie, has kept him out of the headlines for much of the past decade.

In an interview with the Daily Beast podcast The Last Laugh, Cook attributed this lull to typecasting in the industry and a feeling of personal fulfillment. “I took comedy to everywhere I dreamed of taking it. There wasn’t a place left that I wanted to bring stand-up comedy,” he said. During a comeback media blitz in 2019, Cook mentioned Taylor twice, both times to noticeably reticent reactions from the studio audiences.

People are like, ‘You’re robbing the cradle,’ and I’m like, ‘She hasn’t been in the cradle for nine years…’

“People are like, ‘You’re robbing the cradle,’ and I’m like, ‘She hasn’t been in the cradle for nine years,’” he said to sparse laughter during a 2019 appearance on Jimmy Kimmel Live!

A few months later, he appeared on The Tonight Show Starring Jimmy Fallon where he again harped on Taylor’s age.

“Where people get a little bit persnickety sometimes with the relationship is I’m 47, she’s 20,” Cook said to a few bemused “ohs” that turned into raucous laughter when everyone realized they were equally uncomfortable with the subject. “Oh thank you, that was the best laugh of approval I’ve ever heard,” he added, gesturing to the audience across him.

On social media, at least, it doesn’t seem like there’s a happier relationship out there.

“Spent the day walking downtown, taking pics in the arcade at Fun-O-Rama, and got myself a good ol’ york beach sweatshirt. Playing tourist is so so fun,” Taylor wrote on the day of her engagement, weeks before it was revealed to the world.

For more, listen to Dane Cook on The Last Laugh podcast.

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