The “put a finger down” TikTok challenge started as a playful way to see if you related to something—like whether you’re a “green flag” or a “red flag,” or how innocent (or toxic) you really are.
Lately though, creators have been using it to share personal stories—usually ones so specific, they figure no one else can relate.
That’s exactly what TikTok creator Ruby York (@rubyyork) did in a recent video, which has gone viral with more than 2.4 million views.
She starts by asking viewers to put a finger down “if you were a teenager and dated a professional skateboarder and you were just totally in love with him.”
So far, so good.
But then—of course, there’s a twist. “One day you were at a party with him and you were kissing and some girl walks up to you and pushes you off of him and she’s like, ‘That’s my man.’”
York says she didn’t want to start a fight, so she backed off and let the girl have him.
What happened next?
According to York, the skater ended up marrying that same girl. They had two kids together and moved on with their lives.
Until recently.
“About four days ago,” York says, “you’re living your life and you’re in your 30s now… and you open your DMs, and it’s from said pro skateboarder being like, ‘Hey, do you remember me?’”
Of course, she remembered him. The conversation reportedly quickly turned into an update from the past: The skater acknowledged that he got married and had two kids, but now he was divorced.
Then, he allegedly asked her, “Can I take you out to dinner?” York answered, “No, thank you.”
“They always come back,” she said, concluding the video.
She addresses commenters’ speculations
As the video gained traction, commenters started speculating about who the professional skater might be.
One name popped up again and again: Ryan Sheckler—professional skateboarder and star of the TV series Life of Ryan.
It gained so much steam that Sheckler himself chimed in under the original video—and York responded right away with a follow-up.
“These comments are crazy!” Sheckler wrote. “I’m very much still married and in love with my wife and we are doing just fine! I am curious now about who she is talking about tho!?!?”
York replied to his comment in a video, saying, “I just want to say I never once said it was your name. I never once mentioned you.”
She then dropped a hint for anyone trying to figure it out, referencing two iconic skate films from the 2000s.
“As far as who the person is, the only clue I’m gonna say is the time period and the era is from Elementality Vol. 1, all the way up until Fully Flared,” she explained. “And if you don’t know what that means, then you probably shouldn’t be part of this narrative.”
Other commenters shared more thoughts
In the comments, viewers shared their own reactions—some shocked, some amused.
“So he just, had you on the back burner for all these years?” one person wrote. “I had a crush on him decades ago and then suddenly one day he gave me the ick and I didn’t know why but I just couldn’t stand him.”
Another added, “Bruh I need therapy bc I would’ve been like sure.”
And a third joked, referencing the popular Avril Lavigne song “So you’re saying he was a skater boy and you said seeya later boy?”
@rubyyork They always come back #storytime #datingtok #theyalwayscomeback ♬ original sound – Ruby
The Daily Dot has reached out to York via email for comment.
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