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Come Fan with UsSaturday, June 20, 2026

The funniest/saddest places the Internet has placed sports bets

Covers.com asked Twitter for the “sketchiest” places it had ever placed a bet. The answers were ... something.

Stuart Franklin

Covers.com is not a person. It is a website that pulls together the various betting lines on various sporting events, although we might as well presume that it was one of the people that works at that website who took to Twitter earlier this week with a seemingly innocuous question.

Generally, this sort of #brand-to-human communication comes off uncanny and sort of wrong, landing on a vibe something like a Stop&Shop self-checkout station attempting to make Siri-voiced small talk about Derek Jeter. In this case, though, the question asked by a gambling website’s Twitter elicited a series of beguiling, weird, intermittently very depressing, and otherwise extremely human responses.

If this sort of virtual human/brand interaction is what The Singularity is going to look like, let’s at least give it points for being honest about being a terrible husband and having done federal time in Oregon.

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