Reality TV viewers met Bukowski on Emily Maynard’s season 8 of The Bachelorette, which aired in 2012. After finishing as the runner-up on season 3 of Bachelor Pad, he attempted to join Andi Dorfman’s season 10 of The Bachelorette. Bukowski went on to appear on seasons 1, 2 and 6 of Bachelor in Paradise. While he seemingly found The One with Katie Morton on the 2019 installment, they called off their engagement that December, months after the Mexico proposal aired.
Redman, meanwhile, competed for Matt James’ affections on season 25 of The Bachelor before hitting the beach for season 7 of BiP during summer 2021. She left the series solo.
Joe Amabile and Serena Pitt, who appeared on the 2021 season of the spinoff with Redman, introduced the copywriter to Bukowski months after BiP season 7 wrapped.
“I forgot exactly how it went down, [but] Serena is friends with Anna, so Serena was, like, on the phone with Anna. I think she [had] mentioned, like, she’s sick of being single,” Amabile recalled on an April 2022 episode of his “Click Bait” podcast, noting the details are fuzzy. “And then that night, I met up with a few people to watch whatever game was on — I think there was some sporting event on. And I met with Chris and I think he was like, ‘Yeah, I’m sick of being single.’ I was like, ‘Well, I actually know somebody who is also sick of being single.’”
The former grocery store owner subsequently gave Bukowski Redman’s number. “I think I texted Serena. I’m like, ‘Hey, I think Chris would be into Anna,’ and then that was it,” Amabile continued. “He knew she was because Chris is from Chicago, she lives in Chicago. He knew she existed. And he’s like, ‘Yeah, definitely that’s my type.’”
The twosome went public with their romance in March 2022 after months of speculation.
“Hard launch,” Redman wrote alongside snaps of the pair via Instagram at the time.
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