Taylor and Harry were first linked back in December of 2012, and even though they only dated for a couple of months, their romance inspired half of Taylor's 1989 album.
Just like Taylor, Kendall only briefly dated Harry after they were first linked in November 2013.
Dating all the way back to 2008, you could frequently catch them making appearances in each other's vines, and they even shot You Tube videos together.
In 2012, Josh started dating actress Zoey Deutch, and they even got serious enough to spend the holidays together before calling it quits.
Taylor even went on a double date with Gigi and Joe.