Scott Disick

An entrepreneur and self-proclaimed Lord, Scott Disick gained fame on E!’s Keeping Up With the Kardashians as the on-again, off-again boyfriend of Kourtney Kardashian.

Disick and Kardashian, who first got together in 2006, split in February 2009 after Kardashian suspected her boyfriend of cheating. In August 2009, Kardashian announced that she was pregnant with Disick’s baby and the duo reunited. Their son Mason was born in December 2009.

Disick proposed to Kardashian in 2010, but she said no. Despite the rejection of marriage, the couple stayed together. They welcomed daughter Penelope in July 2012 and son Reign in December 2014.

Known for his partying and alcohol and drug abuse, Disick checked himself into rehab in March 2015 but stayed less than one week. Kardashian then broke up with him in July that year. In October 2015, Disick entered rehab once again.

Although Disick and Kardashian are no longer dating, the two are often spotted spending time together and keeping in communication as they raise their children.