Chronology of the relationship between Chris Bukowski and Anna Redman from Bachelor Nation


A marriage made outside of paradise! After Chris Bukowski seemingly left Bachelor Nation (again), he met Anna Redman, the former star of Bachelor in Paradise.

Viewers of the reality show met Bukowski in the 8th season of Emily Maynard’s “Bachelorette Party”, which was broadcast in 2012. After finishing second in season 3 of “The Bachelor Apartment,” he tried to join Andy Dorfman’s season 10 of “The Bachelorette.” Bukowski went on to appear in seasons 1, 2 and 6 of Bachelor in Paradise. Although he seemingly found The One with Katie Morton in the 2019 edition, they called off their engagement in December of that year, a few months after Mexico’s proposal was aired.

Meanwhile, Redman fought for Matt James’ affections in season 25 of “The Bachelor,” and then went to the beach in season 7 of BiP in the summer of 2021. She left the series alone.

Joe Amabile and Serena Pitt, who appeared in the 2021 spin-off season with Redman, introduced copywriter Bukowski a few months after the conclusion of season 7 of BiP.

“I forgot exactly how it happened, [but] Serena is friends with Anna, so Serena talked to Anna on the phone. I think she mentioned that she was tired of being single,” Amabile recalled in an April 2022 episode of his podcast “Click Bait,” noting that the details are fuzzy. “And then that night I met with a few people to see what kind of game was going on — I think there was some kind of sporting event. And I met Chris, and I think he said, “Yeah, I’m tired of being single.” I said, “Well, I do know someone who is also tired of being lonely.”

Subsequently, the former grocery store owner gave Bukowski Redman’s phone number. “I think I texted Serena. I’m like, ‘Hey, I think Chris would love Anna,’ and that’s it,” Amabile continued. “He knew it was her because Chris is from Chicago, she lives in Chicago. He knew she existed. And he’s like, “Yeah, that’s definitely my type.”

The couple made their romance public in March 2022 after months of speculation.

“Tough launch,” Redman wrote along with the couple’s Instagram shots at the time.

Scroll through their timeline:

End of 2021

Amabile did not give a specific date when he told Bukowski to contact Redman, but made it clear that the bar owner should act quickly.

“I thought, ‘Chris, do it now.’ I was like, “Text her right now while it’s fucking hot in the kitchen, because if you wait, she might not answer,” he recalled in “Click Bait.” in April 2022. “I’m like this:”This is the perfect time, you have to take advantage of the moment.””

January 2022

After keen-eyed fans noticed Bukowski and Redman sharing social media posts with similar backgrounds, he was asked about their relationship during a January 2022 appearance on the “She’s All Bach” podcast.

“I’m not going to confirm or deny these accusations. But I know Anna. She’s a great girl. … We’re definitely friends. I like spending time with her,” he said. “I’m just really enjoying my time, you know, currently dating, and I don’t want to draw extra attention to it in any way, because sincerely, like, for the first time in a long time [I’m] happy without stress behind it. [I’m] just, you know, enjoying good company. …Stress-free, very free, very natural. It’s all very unexpected, but obviously, you know, I’m happy that this is happening to whoever it is.”

March 2022

The couple was at a wedding in Costa Rica when they made an official Instagram.

April 2022

Redman called herself a “crazy kitten” during a Q&A on Instagram. “That’s it. This person is the kindest, most caring, best, sweetest, most wonderful [literally insert all the good things] person I have ever met,” she said.