07/22/2009 AT 06:05 AM EDT
's recent estrogen-filled weekend
hanging out with her girlfriends and watching chick flicks with her mom was a welcome bright spot in an otherwise difficult week for the newly single singer.
Since Tony Romo broke up with Simpson on the eve of her 29th birthday, "She's a little depressed," says a Simpson family friend.
"She takes breakups really badly," adds another source close to Simpson. "She has a hard time letting go."
The singer-actress has had a rocky romantic record, which includes her divorce from Nick Lachey
and her on-again, off-again relationship with John Mayer
. But Romo seemed an ideal fit for Simpson, who last year called the Dallas Cowboys quarterback "the love of my life."
So far, Simpson has been coping with the split by living a low-key life and seeking solace with her parents, who "encourage her to go out and have a good time, like she did this week," says the Simpson family friend.
But when she's out in public, "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] 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 she just can't catch a break."
With reporting by K.C. BAKER