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2005

Jessica Simpson

October

Simpson's Operation Smile

Simpson takes a 10-day trip to Kenya as a goodwill ambassador for Operation Smile, an international charity that provides free reconstructive surgery to children born with facial deformities. Lachey does not accompany her on the trip. In the November 2006 issue of Jane magazine, she pinpoints this trip as the beginning of the end. "I went there on our three-year wedding anniversary," she says to the magazine. "He stayed home."

Jessica Simpson

November 23

Newly Separated

After denying reports of a marital rift for several months, Simpson and Lachey announce their separation. "This is the mutual decision of two people with an enormous amount of respect and admiration for each other," they say in a statement. Simpson files for divorce in December, and it is finalized the following June.

2006

Jessica Simpson

October 06

Work & Love

Simpson's second film, Employee of the Month, hits theaters. Playing the hot employee at a warehouse superstore opposite Dane Cook, Simpson gets the chance to showcase her comedic chops. A month later, Simpson also seems to have moved on romantically as she is seen with singer John Mayer at Paradise Cove Café in Malibu and other L.A. nightclubs.

2007

Jessica Simpson

January 01

The New Year With Mayer

Simpson and Mayer spend New Year's Eve together in New York, and then Simpson visits the musician on tour in Miami. When Mayer is asked by Ryan Seacrest about his frequent companion, Mayer responds in Japanese saying, "She's a lovely woman and I'm glad to be with her." The pair date until May 2007.

Jessica Simpson

December 16

Jessica Supports Her Cowboy

Simpson, 27, supports her new man 27-year-old quarterback Tony Romo at a Dallas Cowboys game. With a miniature Romo jersey, a dolled-up Simpson proves to be a distraction for Romo, who throws three interceptions and fumbles the ball twice before losing the game. With her attendance spawning negative headlines, she opts for a vacation with her boyfriend instead of cheering at his games.

2008

Jessica Simpson

Spring

'Can You Feel' The Love?

"I love this guy," Simpson tells Glamour. "Can you feel it?" The guy in question is Romo, her steady since Thanksgiving. Simpson, who recently fed the QB cake at his birthday bash and danced with him at her sister's wedding, says, "What he's done for me is irreplaceable. He reintroduced me to myself." In 2009, Romo breaks up with Simpson the night before her 29th birthday.

Jessica Simpson

May 28

Country Music's Next Blonde

Simpson returns to music with a new single, "Come On Over," off of her country album, Do You Know. When the LP debuts in September, it hits No. 4 on the Billboard album chart, selling 65,000 copies. "She's a singer from top to bottom," Simpson's father tells PEOPLE. "And everything in the music business, especially pop music, has moved away from singers. And I think country is the only pure, storytelling kind of genre left."

2009

Jessica Simpson

January 25

Body Bullying

Photos of Simpson performing at the 99.9 KISS Country Chili Cookoff feature the star's new curves in unflattering mom jeans that spark national news criticizing her weight. "I am completely disgusted by the headlines concerning my sister's weight," her sister Ashlee says.

2010

Jessica Simpson

March 15

Jessica's Real 'Beauty'

Simpson returns to her reality TV roots, producing and starring in VH1's The Price of Beauty, where she travels the world exploring different beauty rituals. "It changed me completely because I haven't always had an inner confidence," the singer says of her show. "The journey really was finding something beautiful inside me, and [knowing that] I own it."

Jessica Simpson

May

A 'Better' Offer

Called "sexual napalm" by ex John Mayer, Simpson finds a steady in former San Francisco 49er Eric Johnson. "I love him!" she later gushes to PEOPLE. "I couldn't ask for a better man in my life right now." In November, Johnson proposes with a Neil Lane ruby ring – and Simpson says yes

Photo Credits

BIOGRAPHY (top to bottom): Joe Simpson; amazon.com; Splash News; LM Otero/AP, Dave Einsel/Getty Images; Flynet; amazon.com; VH1; Grifoni Sarmiento/Splash News Online

Edited by Julia Wang

Jessica Simpson

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