Aired: May 12, 2012 (season 16 finale)

Easygoing Rafael Nadal lookalike Ben Flajnik had major audience support after his incredibly raw and angry reaction to Ashley Hebert's humiliating rejection of his proposal on The Bachelorette. All that emotional capital was quickly squandered when he was the man handing out the roses. He quickly lived up to every horrible cliché falling for resident model mean girl Courtney Robinson, whose serial baby-talking and Charlie Sheen-style declarations that she was ''Winning!'' rubbed everyone — on and off the TV — the wrong way. Despite being the very definition of the ''here for the wrong reasons'' contestant, Courtney's strategically half-naked rule-breaking (including a late-night skinny dipping session) assured she had the repeatedly warned, nobody-to-blame-but-himself Flajnik wrapped around her little finger. When their just-for-show engagement was on the rocks by Ben's After the Finale Rose episode, the bitter far outweighed the sweet in terms of satisfaction. —Sarah Caldwell

SPOILER ALERT: The next slide features plot details from the How I Met Your Mother series finale (originally aired March 31, 2014). If you'd prefer not to know what happened, click the link to skip over it and see the rest of our frustrating TV finale picks.