John Mayer and Katy Perry - The couple co-wrote the song for Mayer's album 'Paradise Valley' (2013) and appeared in the music video together. But they parted ways less than a year later.
Demi Lovato and Joe Jonas - Together they recorded the song 'This Is Me,' which featured on the 'Camp Rock' (2008) soundtrack. The pair didn't stick together after 'Camp Rock.'
Chris Brown and Rihanna - They collaborated on a track for her album 'Unapologetic' (2012). But by May 2013, Chris Brown confirmed in an interview that the two had broken up.
Drake and Rihanna - Most famously, they worked together on 'What's My Name' (2010), but Rihanna also featured on Drake's 'Take Care' (2012). They reportedly split in 2016.
Jessica Simpson and Nick Lachey - When they recorded 'Where You Are' (2000), they had been dating for two years. They had a number of joint musical pursuits before they split in 2005.
Jennifer Lopez and Marc Anthony - They first met during the 1990s, and they recorded the duet 'No Me Ames' in 1999. They toured together in 2007 before they parted ways in 2011.
Mac Miller and Ariana Grande - While together, they recorded the duet 'My Favorite Part' (2016). The couple split in 2018, just months before Miller would die tragically from a drug overdose.
Jason Derulo and Jordin Sparks - Together they recorded the song 'Vertigo,' which appeared on Derulo's 2013 album 'Talk Dirty.' Derulo and Sparks parted ways in 2014.
Halsey and Yungblud - Ashley Frangipane (Halsey) and Dominic Harrison (Yungblud) dated for a very short time during 2019, but they did manage worked together on the rock duet '11 Minutes' (2019).
Wiz Khalifa and Amber Rose - The couple worked together on the track 'Never Been (Part II).' Rose filed for divorce in 2014, citing irreconcilable differences.