1. Bentley Williams, The Bachelorette Season 7
He's not called "Bad News Bentley" for nothing. On paper, Bentley Williams was great — a good-looking single dad from Utah. Unfortunately, as he expressed multiple times to the cameras, he was disappointed that Ashley Hebert turned out to be his season's Bachelorette, deeming her an “ugly duckling.” But, instead of just being honest with her, he toyed with her emotions and played the game, pretending to care while insulting her during his confessionals. Ashley's fellow Bachelor Season 15 contestant Michelle Money was friends with Bentley's ex-wife and warned Ashley ahead of time that Bentley was there for the wrong reasons, but Ashley wanted to make up her own mind. She fell hard for Bentley, and her emotional collapse at his decision to leave the show led viewers to start disliking her, too. Bentley came back later in the season to give Ashley closure, but viewers saw it as an opportunity for him to get a free trip to Thailand. Bentley is still the only suitor to be shown openly dissing a Bachelorette behind her back, making him a strong contender for "Most Hated Contestant Ever."