That same month, The Bachelorette alum Joe Amabile proudly revealed on his "Click Bait with Bachelor Nation" podcast how he had hooked Chris and Anna up because he's pals with Chris and his fiancee, Serena Pitt, is close friends with Anna.
Joe recalled both Anna and Chris saying earlier this year that they were "sick of being single."
Anna, who originally competed on Matt James' season of The Bachelor, and Chris, who has appeared on multiple seasons of The Bachelor franchise, started out as friends before they became exclusive.
"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.