Jessica Simpson's weekend girls' night out was a welcome bright spot in an otherwise difficult week for the newly single, alleged singer and actress.

Since Tony Romo dumped Jessica Simpson before her 29th birthday, "She's a little depressed," says a family friend of the rapidly declining star.

"She takes breakups really badly. She has a hard time letting go."

Her romantic track record, which includes her divorce from Nick Lachey and her on-again, off-again relationship with douchebag singer John Mayer.

But Tony Romo seemed an ideal match for Jessica Simpson, who last year called the playoff-winless Dallas Cowboys quarterback "the love of my life."

Jessica Simpson has also been working out. [Photo: Fame Pictures]

Simpson has been coping by seeking solace with her parents, who "encourage her to go out and have a good time, like she did this week," says the friend.

But "she feels she's being judged by the world and opts to hide out at home," says the friend. "The family feels bad for Jessica. They worry for her a lot."

That wasn't always the case. "The family used to have such faith in [Jessica Simpson] and they worried about Ashlee," says the family friend.

"Now they are fully confident in Ashlee's choices and they worry most of their days about Jessica. It seems that she just can't catch a break."