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The funny thing is, Simpson isn't even his most inappropriate choice as of late.
In April he went to the Bravo A-List Awards with D-list internet skank Tila Tequila.
And before we watch her return to reality TV on Monday night (March 15) with her show, "The Price of Beauty," on VH1, MTV News decided to take a look back at the highs and lows of her career and personal life so far.
November 23, 1999: Simpson released her debut album, Sweet Kisses.
Jessica Simpson was spotted out on a date with her husband Eric Johnson this past weekend in NYC – and it looks like the heels she wore may have been a bit too big.
The 35-year-old's foot was photographed sliding out of the front of her shoes, making her toes nearly touch the ground. (Photo Credit: Splash News) Click through the gallery to see more celebs whose feet have given us pause.
And they didn't waste any time."We had sex the first night we met," he said, before also sharing that he told his new gal-pal, "I think you're the hottest girl in the entire f---ing universe."Smooth. In 2009, the actress was spotted having a lunch date with Adam following her split from model Paul Sculfor.
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Branded as a cleaner-cut pop star than cotemporaries Christina Aguilera and Britney Spears, the 19-year-old didn't roll around in the sand or get her Lolita on in schoolgirl uniforms.
Simpson became the pop-star-next-door thanks to her ballad, "I Wanna Love You Forever," followed by her duet with Nick Lachey "Where Are You." 1999: She began dating Lachey after touring with his band, 98 Degrees.
News today that the Maroon 5 frontman is engaged to Prinsloo after proposing last weekend in Los Angeles.
You may have heard—either by the shriek from your neighbor or the sobbing phone call from your bestie—that the hunky musician has popped the question to girlfriend Behati Prinsloo, shattering the dream of many who hoped of one day becoming his next love interest.(No, but really, congratulations.)The singer's rep confirmed to E!