Years Active: Summer 2015
Probability They Were Actually Dating: 70%
Another reported Summer 2015 romance, Kendall was connected to Orlando Bloom, a 38-year-old recently divorced father. Kendall is just Orlando’s type (dark hair, way younger), so this really isn’t that shocking a duo. Plus, they were spotted on a few dates, according to sources. If Orlando hadn’t claimed he doesn’t even have Kendall Jenner’s number while accepting a Humanitarian Award that fall, this could have possibly been a sure thing.