Bachelor Nation’s Chris Bukowski and Anna Redman’s Relationship Timeline

Credit: Courtesy Anna Redman/Instagram

Bachelor Nation's Chris Bukowski and Anna Redman's Relationship Timeline

A match made outside of Paradise! After Chris Bukowski seemingly retired from Bachelor Nation (again), he met Anna Redman, a fellow former Bachelor in Paradise star. 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. [jwplayer nUF6mhgX-zhNYySv2] 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. Scroll through for their timeline:

Credit: Jordan Strauss/Invision/AP/Shutterstock

Late 2021

Amabile didn’t give a specific date for when he told Bukowski to contact Redman, but he made it clear the bar owner should act quickly.

“I was like, ‘Chris, do it now.’ I'm like, ‘Text her right now while the kitchen is f—king hot because if you wait, she might not respond,’” he recalled on “Click Bait” in April 2022. “I’m like, ’It’s perfect timing, you gotta take advantage of timing.’”

Credit: Courtesy Chris Bukowski/Instagram

January 2022

After eagle-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 those allegations. But I know Anna. She’s a great girl. … We’re definitely friends. I enjoy spending time with her,” he said. “I’m just really kind of enjoying my time, you know, currently dating, and I don’t want to put an extra spotlight on it by any means because genuinely, like, for the first time in a long time, [I’m] happy with no stress behind it. [I’m] just kind of, you know, enjoying good company. … No stress, very free, very natural. All of it very unexpected, but obviously, you know, happy that it’s happening with whoever that might be."

Credit: Courtesy Anna Redman/Instagram

March 2022

The couple were at a wedding in Costa Rica when they made things Instagram official.

Credit: Courtesy Chris Bukowski/Instagram

April 2022

Redman called herself a “smitten kitten” during an Instagram Q&A. “Y’all. This man is the kindest, most thoughtful, best, cutest, loveliest, [literally insert every good thing] person I’ve ever met,” she gushed.

He reposted the Instagram Story, adding, “Go team” with a red heart emoji.

Credit: Courtesy of Anna Redman/TikTok

September 2022

“And they were roommates,” Redman captioned a TikTok video with Bukowski as they kissed in their new kitchen.

Credit: Courtesy of Anna Redman/Instagram

November 2022

Shortly after the Bachelor Nation pair moved in together, they adopted a Schnauzer and poodle mixed-breed pup.

“WE GOT A PUPPY!!!! Her name is Dolly Jo Bukowski-Redman & she’s very loved,” Redman gushed via Instagram, sharing the canine’s first pic.