Bachelor Nation couple Chris Bukowski and Anna Redman have revealed how exactly they began dating and the bold moves Chris made to advance their relationship.

Following months of dating speculation, Anna and Chris went Instagram official with their relationship in March 2022 by posting photos from a wedding they had attended together in Costa Rica.


Bachelor in Paradise spouses Joe Amabile and Serena Pitt previously revealed they had actually hooked up Chris and Anna, who currently live together in Chicago, IL, and now the friends are spilling the details of how that all went down.

Chris and Anna opened up about the first few weeks of their love story during the May 11 episode of the "Click Bait with Bachelor Nation" podcast.

The podcast's co-host Joe Amabile kicked off the story by sharing, "It was the night before Thanksgiving [2021]... It's freezing cold out and Serena was feeling a little under the weather, so I was going to meet some friends and Chris Bukowski so happened to be one of them."

Joe and Chris recalled how they had met up at a popular bar in Chicago called Butch McGuire's but it was so crowded that they decided to leave.

"It was me, you, and one of your buddies, I guess," Chris noted.

After Joe pointed out how Clay Harbor was with them, Chris continued, "We walked over to the bar across the street because it was so packed at Butch McGuire's and we were watching some game and then we started talking."

Joe said he and Chris were betting on sports and talking about crypto before the conversation took a turn into Chris' love life and relationship status.

"You mentioned that you were single," Joe said.

"And I was like, 'Oh, that's actually funny you said that because Serena was just on the phone with Anna before I left and she was complaining about being single.' And I was like, 'This could kind of be perfect.' So I texted Serena and she was like, 'I'll ask Anna.'"


Joe then revealed to Chris at the bar that Anna seemed "into" him and he "should hit her up."

Chris therefore reached out to Anna on social media.

"So then I slid into the DMs and shot her a message," Chris disclosed.

"I have to look back to see what it says, but I'm sure it was great. And then she responded and [Joe] was like, 'You have to hang out with her tonight because if not, you're going to blow it!' So I was like, 'Okay, I'll hang out with her tonight! I had nothing else going on anyway.' And I hit up Anna and of course she was in Minnesota."

Anna went on to share her side of the story and how Joe didn't exactly keep his cool as the couple's matchmaker.

"Joe, I also remember that you DMed me with his Instagram handle saying, '@chrisbukowski thinks you're hot and he's single, successful, and chill. You guys should date!'" Anna recalled with a laugh.

"And a lot of people were talking you up, [Chris]! So I was like, 'I've got to do it!'"

Anna said she decided to give Chris a shot and so she responded to his message "right away."

Anna shared, "I was sitting on the couch with my family back home in Minnesota and we were watching Hallmark movies or something. All of a sudden I was like, 'Mom, guess what? Chris Bukowski thinks I'm hot.'"

Anna admitted everyone was looking over her shoulder, trying to figure out how she was going to reply to Chris' DM.

"That was me with my mom and my sister responding to Chris," Anna noted.

While Chris looked for love five times on different The Bachelor spinoffs and came up empty, he said, "With the show, what it comes back to, is [without it], I would've never met Anna."

"I would have never met Anna if it wasn't for the show or knowing [Joe]," Chris elaborated. "[The franchise] gives you this openness of wanting to connect with other people... It is obviously a great story."


Chris then took Anna to a tavern restaurant for their first date since she doesn't like seafood.

"Actually, he did something amazing that I think all guys should take note of. When I said 'yes' to a date, he sent me two options, and he was like, 'I already have reservations at both of these, which one do you want to go to?' It was so smooth," Anna gushed.

Chris, who was living in Denver at the time, was home in Chicago for Thanksgiving to visit his family and so he got a hotel the night he took Anna out.

"It was a Monday night and they kicked us out," Anna proudly stated. "We stayed until I think it was 11:30PM, and they were like, 'You guys have gotta leave,' which was kind of embarrassing -- but it was a good date!"

When asked if he thought the relationship could go the distance after just one date, Chris admitted he was "very attracted" to Anna and she's "absolutely" his type.

"So I was super excited, because honestly, up to that point, I just kind of threw in the towel, like, 'I'm good. I'm just chilling and having a great career and just seeing what happens,'" Chris confessed.

"So I wasn't really forcing the issue, and that's why I'm so lucky and happy that it happened."

About two weeks after their first date, Chris admitted he received an invitation in the mail for a wedding in Costa Rica and made the bold move of filling in Anna's name as his plus-one -- without even asking her first.

Anna said once Chris asked her to go on the vacation with him, she was totally onboard.

"It was a little fast, but hey!" Anna joked.

"I was really excited. I didn't have many expectations going in, because you never know, and then also, this man has a sparkle you just don't see through a screen, and I was just smitten."

Anna gushed about Chris' great smile and blue eyes, and Chris ultimately committed to a move to back to Chicago, where his family resides.

"We're now looking at other possible places to live, like South Carolina," Chris said.

"I think we both want to be on the ocean at one point and always have a home base in Chicago," Anna added.

Anna originally competed on Matt James' season of The Bachelor, and Chris appeared on "five-and-a-half" seasons of The Bachelor franchise.

Chris began dating Anna after his failed engagement to Katie Morton, whom he proposed marriage to on Season 6 of Bachelor in Paradise in 2019.

Chris and Katie worked on their relationship for several months but announced they had decided to call it quits and end their engagement in December 2019.

In January 2022, Chris said on the "She's All Bach" podcast that his dating life was "good," according to Us Weekly.

"You know, it was bad for a while. After Katie, I didn't date anybody really. Recently, it's been pretty good," Chris said.

But Chris wouldn't admit that he had a romantic connection with Anna brewing at the time.

"I'm not going to confirm or deny those allegations," Chris said of dating rumors that had been floating around. "But I know Anna. She's a great girl... We're definitely friends. I enjoy spending time with her."

Chris said he was really enjoying his time dating off-camera and on his own terms.

"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," Chris shared on the podcast.

"[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."

Chris found fame when he competed for Emily Maynard's heart on The Bachelorette's eighth season. He later appeared on Season 3 of Bachelor Pad and finished as the runner-up.

Chris crashed Andi Dorfman's season of The Bachelorette but she rejected his advances and didn't allow him to join the cast.

Chris then returned for Season 1 of Bachelor in Paradise, after which he announced his retirement from The Bachelor franchise. However, he decided to look for love once again on television via Season 6 of Bachelor in Paradise.

For Anna's part, she attempted a relationship with James Bonsall in Paradise in Summer 2021 but left the show single.


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About The Author: Elizabeth Kwiatkowski
Elizabeth Kwiatkowski is Associate Editor of Reality TV World and has been covering the reality TV genre for more than a decade.