The 49-year-old was talking to Ali on-air as she's currently starring in SAS Australia and shared how "remorseful" he felt after seeing her cry on the show while speaking about her breakup with Taite Radley.
The shock jock would often bring up rumours that Ali was caught in a sex act on a staircase by ex-boyfriend Grant Kemp with one of his friends, however, after seeing Ali's interrogation on the show, he changed his tune.
"I was watching it by myself on the chair at home and I teared up when you started crying, because I thought, 'Jesus, I'm part of that culture that talked about you shone the spotlight on things you may not have wanted to talk about’,” Kyle said.
"And I felt, for the first time ever, very remorseful about my part in that, so I just wanted to let you know that."
He added: "You suffered it, you had the anxiety and all that stuff, and I felt like a piece of s**t."
Clearly, Ali hadn't expected to hear this apology and seemed taken aback by the admission, but thanked him.
"I regret that, I didn't realise that you were going through such a tough time," Kyle said.
"It felt fun at the time ... you forget sometimes that people on TV are real human beings."
Just last week, Kyle brought up the staircase scandal while chatting with Firass Dirani.
"We haven't seen Ali be interrogated yet, but do you think they'll bring up when she [engaged in a sex act] on the stairs?" he asked the actor.
Firass laughed awkwardly, attempting to deflect the question, "Um... what time is it? Is it too early for this? Are the kids on the way to school yet?"
Ali's ex Grant publicly accused her of cheating on him with a friend of his, claiming he walked in on them on a staircase at his home in Los Angeles.
The reality star never denied the incident, but has been quizzed by Kyle about it in the past.
Before the Bachelorette finale, Kyle questioned her about the incident and she told him he'd gone too far.
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