current events | January 16, 2026

Kenny Chesney says he didn’t break up Jessica Simpson and Tony Romo

jessica simpson macys 071208
I have to say, I am rather surprised by all the media coverage of the Tony Romo-Jessica Simpson breakup. To me, they were one of the most boring D-List couples in Hollywood. A washed-up pop-turned-country singer airhead and her dingbat jockstrap of a boyfriend. Snooze city! But since the breakup, numerous theories on what ended the relationship have surfaced: Tony was cheating on Jessica because she was needy, a drunk, or too fat. Jessica was cheating on Tony with John Mayer. Tony was having an emotional affair with some other blond bimbo that he met at a Jessica Simpson show. And here’s the latest: Tony dumped Jessica because she was flirting with country singer Kenny “I’m Not Bald, I Swear!” Chesney at a 4th of July barbeque.

Kenny Chesney is blasting a tabloid report that he and Jessica Simpson flirted in front of Tony Romo at a July 4 party just days before the couple’s breakup.

“Tony’s a friend, and I wouldn’t flirt with a buddy’s girlfriend,” Chesney tells PEOPLE. “More importantly, Jessica was just being sweet and there was nothing else to it. It’s not funny. There were no problems. Everybody got along great. After the party, everybody went their own way and nobody thought anything more about it. Period. End of story.”

The party was thrown by Chesney’s friend, Sean Payton, coach of pro football’s New Orleans Saints, Chesney says.

“If a girl and her boyfriend can’t go to someone’s house for a Fourth of July party and talk to the other guests without it turning into a big nightmare … , then I feel really sorry for Jessica and Tony, who’re both really nice people,” Chesney says. “I wonder if I wasn’t famous if anyone would even care. But the fact of the matter is I talked to a bunch of guests, hung out, had a good time.”

Simpson and Romo, the quarterback for the Dallas Cowboys, split five days later on July 9 – the night before Simpson’s 29th birthday.

[From People]

Well, Kenny, that’s awfully nice of you to set the record straight. And you are right – if you weren’t famous, nobody would care. In fact, I’m finding it awfully hard to care even though you are famous. Seriously- did anyone think these two were going to last? Get back to me when she’s dating someone interesting.

Jessica Simpson is shown no 12/16/08. Kenny Chesney is shown on 5/19/09. Credit: WENN.com