After panellist Tommy Little laughed awkwardly, Kyle suggested he knows more about their relationship than we do, implying the seemingly perfect couple's marriage is on the rocks.
"Hmmm... I feel there's trouble there," the 48-year-old continued. "No, no there's no trouble there," he then said, mimicking Anna."Watch that space. Something's going on!"
Realising he was a little too harsh, Kyle backtracked saying: "They're a super nice couple, they're like what we all pretend we want to be, we just know it'll never be right."
Kyle also took a dig at the couple live on air yesterday morning on The Kyle and Jackie O show, saying he was, once again, "worried" about their long-term relationship.
"I think that Tim has abandoned her with the move down to Melbourne for Neighbours. She's still living in Sydney, and that worries me. 'He's moved down there permanently and he's left her behind."
After being alerted of his nasty comments, the 37-year-old— who rose to fame after handing out roses on The Bachelor and later married Anna in 2018— told the Daily Mail that "Anna and I knuckle down into work during the week and have plenty of quality time on the weekends."
He continued: "We're actually surprised how well we've made the circumstances work. I was getting a little jealous of how much she was saying she loves Kyle but hopefully they just keep that romance in the courtroom"
As we know, the reality TV star turned actor permanently moved to Melbourne in March after landing a full-time role on Neighbours. While Anna previously said the move was tough, the couple sees each other every weekend.
While the controversial radio personality didn't hold back, Anna recently said working with Kyle on their Network 10 pilot series, Trial By Kyle, was an absolute treat.
“That is the number one question people ask me,” Anna said. “But I had a really enjoyable time working with him. He is so fabulous and I don’t think anyone else could be put in that situation and do as well as him.
“Initially, when I heard about the show and I heard that Kyle was doing it I didn’t know how it would work, only because I’ve only ever seen Judge Judy."