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[TOMT] [movie] [tv] [early 2000s] Help solve the mystery between a family joke.
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ThankfulImposter is in TV
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There is a running joke between my husband and I where he makes a goofy smile that exposes his teeth and says, "Will you skate with me?"

He explains that back in the early 2000s he and a friend were flipping channels and watched a short clip where a kind of needy boy walks up to a girl and asks, "will you skate with me?" Then smiles big and off-putting. They changed the channel shortly after. Clearly the clip made an impression on him because he still talks about it 20 years later.

I know it's a long shot but does anyone happen to remember seeing something like this? I would love to blow my husbands mind by finding the clip and randomly playing it when he's not expecting it.

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9 months ago