Until The Bachelorette can finally start filming , it appears Peter Weber's season of The Bachelor is technically still going. The pilot went from Madison Prewett to Hannah Ann Sluss to Madison Prewett again, but almost as soon as that two-day relationship came to an end, he was spotted with another contestant: Kelley Flanagan. The two were seen strolling by the river in Chicago and later quarantining on TikTok , but no matter how many times fans shouted to the sky in wonder about their relationship status, the pair seemed determined to elude us. Getting to the bottom of that mystery was a job only Nick Viall, Rachel Lindsay, and Becca Kufrin could handle.