Years Active: 2016
Probability They Were Actually Dating: 80%

There have been rumors about these two since spring 2016, and they flared up again this past Fourth of July weekend. Everything about this makes sense. Kendall skews towards the athletic type and Jordan towards the models (a recent ex of his was Chanel Iman). However, like many of Kendall’s “suitors,” there have only been rare sightings of the two, but in the few we’ve seen, they've seemed pretty cozy. This probably happened, but it probably isn’t that serious.