KOURTNEY KARDASHIAN & SCOTT DISICK
The Keeping Up With the Kardashian stars got together in 2006 but split in 2009 due to too many trust issues. They reconciled when Scott surprised Kourtney in Miami, and soon after she became pregnant with their son Mason. Kourtney called it off at least once during her pregnancy, but by the time Mason was born in December 2009, they were back together. They broke up again, with Kourtney saying Scott wasn’t being good enough dad material, but ultimately they were together again and daughter Penelope arrived in July 2012. Together they stayed, despite the occasional bump in the road (usually due to Scott’s partying), and son Reign was born in December 2014. Kourtney called it off for good in July 2015, Scott having partied too hard one too many times.