The Simpson Family is concerned with how 29-year-old star Jessica Simpson is coping with being suddenly single for the hundredth time since her split from Dallas Cowboys quarterback Tony Romo last week.

According to a source close to the Simpson family, her loved ones are worried about the singer.

”[Her parents] encourage her to go out and have a good time, like she did this week,” a family friend told PEOPLE Wednesday.

The family’s attention has reportedly turned from younger sister Ashlee to Jessica.

“The family feels bad for Jessica. They worry for her a lot.”

Although Jessica managed to put on her Big Girl Pants for a Girls Night Out with friends this week, “she feels she’s being judged by the world and opts to hide out at home.”

“The family used to have such faith in [Jessica] and they worried about Ashlee,” the family friend claimed. “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.”