Giuliana Rancic's Forgotten Ex Before Bill Lifts The Lid On Their Split: 'We Broke Up Poorly'

It seems that Giuliana Rancic didn't have the best of boyfriends before settling down with Bill Rancic. Her ex-boyfriend, Jerry O'Connell, admitted that his breakup with Rancic back in 2004 wasn't pretty. The actor and TV show host opened up about his relationship with the entertainment reporter during a July 2026 appearance on SiriusXM's "Let's Talk Off Camera with Kelly Ripa." The split was originally detailed in Rancic's tell-all memoir, "Going off Script," released in 2015. O'Connell provided more pieces to the puzzle while discussing the topic with Kelly Ripa.

"I gotta say, we had a lot of fun together," he reminisced. "But we did break up on — we broke up poorly." This reveal didn't come without an apology. "Let me take this moment to apologize to Giuliana Rancic — I'm not kidding — for being a terrible boyfriend. I was the worst. I wasn't the worst. ... I was just not a great boyfriend." After explaining everything that went down, it's safe to say that an apology was absolutely required. That's right — O'Connell is a celebrity cheater who got caught in the act.

In her memoir, Rancic details how the two ended their relationship over O'Connell's building intercom. O'Connell admitted that he had someone else at his place when Rancic came over unannounced, which is why he didn't let her in. According to Rancic, O'Connell told her, "Nope. Sorry, homegirl. Things change. But you take care, okay?" (via Entertainment Weekly). When faced with his own words, O'Connell told Ripa, "It doesn't sound like something I would say, but, again, if I was writing a memoir, it made for a good quote."

One sad detail that Giuliana Rancic revealed in her memoir is that Jerry O'Connell had cheated on her twice in their short relationship. O'Connell didn't cheat with anyone low-profile either. The first time around, he cheated on Rancic with Geri Halliwell (Ginger Spice) of the Spice Girls, whose love lives have taken some interesting twists and turns. Rancic's harsh bites that she typically saved while co-hosting "Fashion Police" weren't toned down in her memoir when she referred to Halliwell as "one of the lesser Spices" (via Page Six). Despite this, she decided to give O'Connell another chance. The chance didn't last long when she discovered O'Connell getting cozy with his now-wife, actor Rebecca Romijn.

This realization led to Rancic's unannounced confrontation through O'Connell's intercom. O'Connell wouldn't dare reveal who exactly was in his condominium that fateful day he and Rancic broke up, although Kelly Ripa did make sure to inquire. While a relationship didn't work out for them, Rancic and O'Connell have now settled down. Both Rancic and O'Connell married their partners in 2007. At least O'Connell had the guts to admit that he was wrong, which is more than we can say for most infidelitous celebrities.