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After her grandmother stepped in to bankroll her first album 19-year-old Simpson found herself struggling against the massive success of edgier Billboard-toppers Spears and Aguilera. I really feel equipped for what's going to come." But there were growing pains, too.While on tour that year with 98 Degrees, Simpson struck up a steamy, real-life relationship with oft-sleeveless frontman Nick Lachey, after playing his diner-waitress girlfriend in his boy-band's music video, "My Everything". For five months that year, Simpson broke it off with then-boyfriend Lachey.

And we were talking back and forth, all while she was in the trunk," reported in 2008."It's not fair that women look in the mirror and feel disgust because of what society has made them believe about beauty," she said in a 2009 interview with After announcing she was expecting her first child with former NFL tight end Eric Johnson in 2011, a pregnant Jessica Simpson endured even more criticism when haters said she looked like she had "gained too much weight" during her pregnancy.Still, the mama-to-be embraced her new, curvier figure, even posing nude for the cover of The new mom was glowing after the birth of her daughter, Maxwell, though she admitted slimming down post-baby wasn't easy. More than I thought I would," Simpson said, according to .Earlier, in May of that year — in the wake of 9/11, bride-to-be Simpson wiped up the stage at Rockin' for America in Ft.Lauderdale, FL, singing her hit single "Irresistible" for U. servicemen and women, and wearing a "cold shoulder"-style blouse that would trend again over a decade later in 2016.

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"I can't promote squats and step-ups enough," Alexander told , Simpson eased up on her stringent diet and workout routine, although she still hit the gym three times a week.