Booth and Underwood's relationship dates all the way back to January , when they went on a hike in Runyon Canyon together with a couple of foster puppies. (Hence the puppies in Booth's tweet.) Underwood later appeared on Becca Kufrin's season of The Bachelorette, where he admitted to having a history with Booth, one of Kufrin's friends. Underwood did not win that season — he was dumped just before Fantasy Suites — nor did he "win" at Paradise. He left the beach empty-handed after having flickered in and out of a relationship with Booth. If this information seems confusing to you now, never fear: Underwood's season of The Bachelor is going to rehash it and rehash it and rehash it. Booth may not return to the season as a contestant, but she'll certainly materialize as some sort of guidance counselor for her tearful, vest-loving ex.