Selena Gomez has had a turbulent dating history.

Iconic singer and Disney actress Selena Gomez has had several rough and bad patches thrown her way after she became successful in the music industry. From dating Justin Bieber to dating The Weeknd, the singer doesn’t seem to have found the one.

In an interview with David Letterman, the show host joked that the last time Justin Bieber was there on the show, David Letterman made him cry. Laughing at the scene, Selena Gomez stated that she too had made Justin Bieber cry once!

When Selena Gomez Made Justin Bieber Cry

Gomez and Bieber were adored by the world when they were entangled in a romantic relationship in December 2010. Breaking up with the Canadian singer, Gomez focused on her music career while being confused by the nature of her and Bieber’s relationship.

Selena Gomez and Justin Bieber

It wasn’t until 2018 that they announced a final breakup and never got back together. In an interview, Gomez sat down for a chat with David Letterman on the Late Show with David Letterman. During the interview, Letterman and Gomez had a hilarious interaction.

“Now, the last time he [Justin Bieber] was on [the show], he and I got into a conversation. He said something, then I said something and then he said something and something and I made him cry” said Letterman.

Selena Gomez gave out a hearty chuckle and stated,

“Well then that makes two of us.”

David Letterman burst out into laughter and was forced to give Selena Gomez a fistbump as he was essentially left speechless.

Selena Gomez’s Dating History

Gomez had a brief entanglement with The Weeknd

Selena Gomez has had a pretty chaotic dating history over the years. The singer has also suffered a lot of mental and physical health issues over the years which had an impact on her professional career.

Starting with Nick Jonas in 2008, the actress moved on to date Justin Bieber in 2010. From 2010 to 2018, she had an on-and-off relationship with the Canadian singer. In the midst, Gomez dated DJ artist DJ Zedd but broke up that same year.

In 2017, Selena Gomez was romantically involved with The Weeknd and they moved in together for a short while but things didn’t work out with them. Ever since The Weeknd, Gomez has been quiet about her personal life and seems to be focusing on her music career more.

The Weeknd’s infamous HBO series The Idol is alleged to have been inspired by Selena Gomez’s life as they share a lot of similarities but nothing has been confirmed or denied.