Break-Up Rumors, Is Charlie Winston Single Again?

Is the 48-year-old singer officially back on the market?

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Are celebrities more likely to divorce or break up? Earlier this week news reports surfaced that Charlie Winston, 48, and his partner had split up. Is the singer best known for his hit song Like a Hobo really single again?

UPDATE 18/09/2026 : This story seems to be false. (read more)

Winston spotted alone

A fan spotted Charlie Winston walking alone, probably coming back from picking up his mail at the end of his several mile long driveway, on the afternoon of September 16, 2026. Was he all alone? “Definitely yes,” says the fan, adding that “He was wearing a large sweater and looked really cute!”

Is Charlie back on the market?

A rep for Charlie Winston was not immediately available for comment.

Truth or rumor, when news that the singer was splitting hit the internet Thursday (September 17), Twitter immediately exploded with pithy commentary. It seems everyone had an opinion on the matter:

“Has anyone Charlie’s phone number?”
— Michelle Whedon (@mimiwhedon) September 17, 2026

“So very sad… Those 2 were so great as a couple. So cute together.”
— Crystal (@crystal_clear) September 17, 2026

Based on the facts (Winston spotted alone with a cute sweater), is there trouble in paradise or is it much ado about nothing?

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