Jessica Simpson Shades Ex Tony Romo After Unexpected Run-In: Singer Laughs Off ‘Bizarre Interaction’ and Declares She’s ‘So Glad We Didn’t Work Out’

Jessica Simpson has never been one to hold back her feelings — and this week, the pop icon and fashion mogul delivered a shade-filled moment that instantly went viral. After a surprising and somewhat awkward run-in with her former flame Tony Romo, Simpson publicly declared she’s “so glad we didn’t work out,” leaving fans buzzing about the bizarre encounter and the singer’s brutally honest reaction.

The moment unfolded when Simpson, 45, crossed paths with Romo, 45, during a charity event in Los Angeles. According to onlookers, what was supposed to be a cordial exchange between the exes quickly turned into an uncomfortable, almost comical interaction that highlighted the pair’s rocky history. Though Simpson has long since moved on — happily married to former NFL player Eric Johnson — she didn’t hesitate to poke fun at her failed romance with Romo, who is now married with kids.

Speaking to friends after the run-in, Simpson reportedly joked that she was “relieved” their relationship ended when it did. “It was one of those moments where you realize how far you’ve come,” she told a source. “I’m so glad we didn’t work out, and seeing him just reminded me of that in the funniest, strangest way.”

Simpson and Romo dated from 2007 to 2009, a relationship that played out heavily in the tabloids, with the quarterback’s career struggles often unfairly blamed on her presence at games. Their split was messy, with reports at the time suggesting trust issues, miscommunication, and intense media scrutiny were too much for the couple to handle.

Fans have long speculated about lingering tension between the two, but Simpson’s recent comments make it clear she’s moved on with confidence and humor. Social media erupted after her remarks spread, with many praising her for being candid and unapologetically honest about an ex. “Jessica is the queen of saying what we’re all thinking,” one fan posted on X (formerly Twitter). Another added, “That’s the kind of closure we all need with our exes — just laugh and move on.”

While Romo has not publicly addressed Simpson’s playful shade, the encounter highlights how the singer has reframed her past relationships with empowerment rather than regret. In recent years, Simpson has leaned into her brand of transparency, whether in her memoir Open Book or in interviews where she openly discusses heartbreak, motherhood, and growth.

For Simpson, this latest headline-making moment is less about rekindling drama and more about celebrating personal growth. She’s thriving with her family, overseeing her billion-dollar fashion empire, and keeping her sense of humor firmly intact. And if her reaction to Romo is any indication, Simpson isn’t looking back — only forward.

As one fan perfectly summed it up: “Jessica won the breakup — and she knows it.”