3. SELENA GOMEZ AND JUSTIN BIEBER

The teen heartthrobs’ breakup is especially awkward because they just can’t seem to quit each other. They dated on and off from 2010 to 2015 and were even seen hanging out before he got engaged to his now-wife, Hailey Baldwin.

Selena dropped two songs — “Lose You to Love Me” and “Look At Her Now” — at the end of October 2019 that fans think are about her tumultuous relationship with the pop star.