Camille Rowe
Next came a year-long relationship with actress-and-model Camille Rowe - who appeared on the cover of Playboy in 2016.
The two were introduced by a mutual friend in 2017 and rumors of their romance went wild after fans pointed out his voice in an Instagram story posted by Camille.
The ‘Sign of the Times’ singer even introduced Rowe to his family while they were dating and when they broke up he was heartbroken.
Many commentators and fans believe the split was one of the main inspirations for his 2019 album ‘Fine Line,’ although that has never been confirmed by the singer.