The scene was the 2025 Women Who Rock Benefit Concert in Pittsburgh, where Simpson took the stage and delighted the audience with a curious tale. According to fan footage from the event, everything started with a phone call—to her mom.

“A couple weeks ago, my mom got a phone call,” Jessica told the crowd. “It was Tony, calling my mom, saying, ‘Well, Tina, I’m selling the boat.’” Her mother, seemingly puzzled, simply replied, “OK… and?”

Turns out, the boat in question was the same speedboat—reportedly worth around $100,000—that Simpson had gifted Romo for his 28th birthday back in 2009. Apparently, her name was still on the title.

“So then I get paperwork in the mail,” Jessica explained, “and I have to sign over this boat so he can finally sell it.”

But the real punchline came when Romo tried to thank her. Instead of flowers or a heartfelt note, his gratitude came in the form of… plastic cups.

“He gave me plastic cups,” Simpson joked, quipping to the audience: “I was like, ‘Wow… I’m really glad we didn’t work out.’”

The two dated from 2007 to 2009 before going their separate ways. Simpson went on to marry former NFL player Eric Johnson in 2014. The couple share three children: Maxwell, Ace, and Birdie.

Earlier this year, however, Simpson confirmed that she and Johnson had separated after nearly a decade together. In a statement posted in January, she emphasized that their focus remains on co-parenting and putting their children first.

Now, Simpson is making a return to music after stepping away from the industry for more than 15 years. She just released a new project, Nashville Canyon, Pt. 2, on September 4th.

And although she’s been busy with her musical comeback, she was also spotted recently with ex Eric Johnson—while supporting her sister Ashlee Simpson at her Las Vegas residency. TMZ captured video of the two keeping it friendly but low-key among a group of friends. There was no PDA, and no confirmation of anything more—leaving fans guessing about what this reconnection might really mean.