Breakups

Update Monday December 28, 2009 01:00 AM EST Originally posted Monday December 28, 2009 01:00 AM EST

• Facebook
• Tweet

TOGETHER TWO YEARS

Jake Gyllenhaal & Reese Witherspoon

THE SPLIT: One month after she gushed to In Style about spending blissful weekends at her California farmhouse with Gyllenhaal, 29, and her children (Ava, 10, and Deacon, 6) from her marriage to Ryan Phillippe, Witherspoon, 33, gently broke things off with her man around Thanksgiving. Though Gyllenhaal was still calling her his girlfriend Dec. 3, the couple officially agreed to part ways soon thereafter. "[Reese] was so concerned with her family, she just didn't have the time for him," says a source. "He really demanded that."

THE AFTERMATH: Don't expect Witherspoon to move on quickly. "I don't know how I feel about marriage," she told Parade this year. "Obviously, I'm not far enough out of being married to think about doing it again."

TOGETHER TWO YEARS

USHER & TAMEKA FOSTER RAYMOND

THE SPLIT: Usher, 31, filed for divorce from Foster, 38, in June, ending a brief and rocky union.

THE AFTERMATH: The couple are co-parenting sons Usher V, 2, and Naviyd, 1.

TOGETHER ONE YEAR

MAKSIM CHMERKOVSKIY & KARINA SMIRNOFF

THE SPLIT: The Dancing with the Stars duo (he, 29, she, 31) ended their engagement in September.

THE AFTERMATH: Despite awkwardness on-set, "they think it worked out for the best," says a pal.

TOGETHER 13 YEARS

Robin Wright & Sean Penn

THE SPLIT: After having initiated divorce proceedings twice during their roller-coaster marriage, the couple, who have two children together, Dylan Frances, 18, and Hopper Jack, 16, officially threw in the towel in August.

THE AFTERMATH: Penn, 49, quickly moved on with SPORTS ILLUSTRATED model Jessica White, and Wright, 43, isn't looking back. She told More, "I know what I don't want."

TOGETHER SEVEN YEARS

LEANN RIMES & DEAN SHEREMET

THE SPLIT After falling for her married TV-movie costar Eddie Cibrian, 36, Rimes, 27, announced plans to divorce Sheremet.

THE AFTERMATH While Rimes continues her romance with Cibrian, who is divorcing his wife, Sheremet says of life post-LeAnn, "It's liberating."

TONY ROMO & JESSICA SIMPSON

THE SPLIT: After dating the Dallas Cowboys quarterback, 29, for two years, Simpson got dumped on the eve of her 29th birthday in July. "She expected [an engagement] ring for her birthday," a source told PEOPLE. "He wasn't ready."

THE AFTERMATH: While Romo has recently been linked to Chace Crawford's sister Candice, Simpson has been spending time with Smashing Pumpkins frontman Billy Corrigan, who fits the description for what she's looking for in her next relationship. "I love artistic men," she said recently.

TOGETHER TWO YEARS