Years Active: 2013-2014, and 2016
Probability They Were Actually Dating in 2013-2014: 100%
Probability They Were Actually Dating in 2016: 30%
Probability Kendall Will Revisit That D Again in 2016: 100%

Kendall’s most public relationship happened during the winter of 2013 and 2014 when she started dating One Directioner, Harry Styles. Their relationship only lasted three months, most likely due to the rampant torture one was required to endure when dating a One Direction member in their prime. Their story didn’t end in 2014, though, as they were linked to one another yet again in February of this year after being photographed on multiple occasions—most notably seen kissing on a yacht. Both of their mothers and Ellen Degeneres were all aboard, so you know there's some real support for Hendall 2.0 (and any future versions).