When Jessica Simpson announced her split from husband Nick Lachey in 2005, she never guessed she'd be the heartbroken one more than two years later.
But it's true - Nick Lachey has been happily seeing Vanessa Minnillo nude for some time, while Simpson has endured a bevy of high-profile, failed relationships.
The list of douchebags the eldest daughter of Joe Simpson has dated is certainly not short - John Mayer, Adam Levine, Orlando Bloom, Owen Wilson, et cetera.
Jessica Simpson: So much regret. So little talent.
"There is definitely a part of her that really regrets breaking up with Nick now," a Jessica Simpson friend tells Us Weekly in the magazine's new cover story.
That regret is starting to show. On October 26 (what would've been her 5th anniversary), Jessica spent the day "looking through old photo albums that she made with Nick... she said she was just being girly, but she was very somber."
"Jessica thought she would be with someone right by now," the pal said.
Could Jessica Simpson, who has recently started dating Dallas quarterback and celebrity gossip mainstay Tony Romo, be her own worst enemy?
Meanwhile, on a November 15 guest host appearance on The View, Simpson, who is currently recording a country music album in an effort to revive her sagging career, seemed to be pining for a guy ... a guy like Nick Lachey:
"I want a man," she said. "Somebody who's a really great family guy... Gosh, just somebody who's strong enough to be my man."