Anna, 25, took to Instagram on Friday and posted two pictures with Chris while attending a destination wedding in Costa Rica as dates.
"Hard launch," The Bachelor 25 alum captioned the post, which included one photo of the blonde bachelorette kissing Chris on a beach.
Chris, 35, commented, "Lucky guy," on Anna's upload and also posted a slideshow of photos with her on his own Instagram account.
"When ordering lobster mac n cheese without lobster starts to make total sense," Chris wrote alongside the sweet images, including one picture of Anna kissing him on the cheek.
Anna, who replied, "It always makes sense," also shared more photos of the couple on her Instagram Story on Friday.
She captioned one photo of the pair making out, "Happy and sun-kissed here in Costa Rica," according toUs Weekly.
Anna, who originally competed on Matt James' season of The Bachelor, and Chris, who has appeared on multiple seasons of The Bachelor franchise, both live in Chicago, IL, and so their romance apparently started out as a friendship.
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.
One month later, Chris said on the "She's All Bach" podcast that his dating life was "good," according to the magazine.
"You know, it was bad for a while. After Katie, I didn't date anybody really. Recently, it's been pretty good," Chris said in January.
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."