Colton Underwood's past relationship with Cassie Randolph - and her restraining order against him - resurfaced during his stint on The Traitors, but what actually happened between the exes? Underwood's love life became a topic of conversation on The Bachelorette when he joined Becca Kufrin's season 14 in 2018. He later appeared on season 5 of Bachelor in Paradise before becoming the season 23 Bachelor lead in 2019. The reality star formed a connection with Randolph that resulted in that iconic fence-jumping scene.