Jared Haibon and Ashley's romance began when they were both were on season two of Bachelor in Paradise. Things seemed to be going well for the most part, until Jared questioned whether or not their chemistry was something that he was looking for. It was later revealed that Jared couldn't fully invest himself in their relationship because he still held a torch for season 11 Bachelorette Kaitlyn Bristowe. Heartbroken, Ashley proceeded to call Bristowe in the confessional, telling her, "he's obsessed with you."