Chris Bukowski

Bukowski made his Bachelor franchise debut on Emily Maynard's season of The Bachelorette in 2012. He reached the hometown dates and was eliminated in fourth place.

He returned that year for the third season of Bachelor Pad, where he partnered with Sarah Newlon and finished as the runner-up. In 2014, he attempted to join Andi Dorfman's season of The Bachelorette on limo night, but Dorfman declined to add him to the cast and security escorted him from the mansion.

Bukowski appeared on the first season of Bachelor in Paradise in 2014 and formed a relationship with Elise Mosca. He left the show with Mosca during the third week after suffering a knee injury. They tried dating after filming but separated after about a month.

He returned midway through the second season in 2015 intending to ask Tenley Molzahn on a date. After Molzahn turned him down, he gave his date card to another contestant and left the beach. Bukowski then announced his retirement from reality television, before returning for the sixth season in 2019. On that season, he met Katie Morton, and the couple became engaged during the finale before announcing their breakup in December 2019.

Bukowski and Anna Redman announced their relationship in March 2022. Although both had appeared on several Bachelor Nation programs, they met off-screen while living in Chicago, Illinois.

Redman has described their age difference as something they discuss occasionally but not as a major barrier in the relationship. She characterized their dynamic as a mix in which Bukowski keeps her wise while she keeps him up to date with newer trends.