For Ashlee Simpson, life sure seems close to perfect. As OK! was first to reveal, the singer, who is engaged to rocker Pete Wentz of Fallout Boy, is also pregnant with their first child, due in late October. And with her new album, Bittersweet World, getting rave reviews from critics, the 23-year old singer has managed to strike her own path with both her career and personal life.

Not the same can be said for older sister, Jessica Simpson. The 27-year old songstress has notoriously struggled under the influence and interference of her manager father, Joe Simpson. It was even rumored that papa Joe was partly to blame for Jess’ divorce from husband Nick Lachey in 2005.

Even now, despite a blooming relationship with Dallas Cowboys QB, Tony Romo, and the sincere happiness she feels for her younger sister, Jessica is once again feeling her father’s presence in her relationship.


Although Jessica and Tony are very much still together (she threw him a 28th birthday party in Dallas on April 19), OK! has learned that Tony and, in particular, his family, may not be loving the fact that Joe Simpson is constantly popping into the picture.

"His [Tony] family’s view seems to be that Jess and her dad, Joe Simpson, are bringing Tony down," a source tells OK!. "I think they are ruining his image, as well as trying to capitalize on his fame, in order to boost hers."

The source also shared a revelation about the Mexico trip that Jessica and Tony took with his teammates in January, before the NFL playoffs. "Everybody agreed to tell no one about the trip," says the source. "On the day they were flying out, who shows up? Joe Simpson. Tony and the other guys thought it was weird."

The private vacation became very public when photos of the group appeared in magazines. Tony, says the source, recently came to the conclusion that Joe tipped off the paparazzi! Friends say the whole situation destroyed any hope Tony may have had of ever taking Jessica seriously. "Tony says they are just friends with benefits," says the source. "The sex is good, but he doesn’t see it going anywhere."

For the full scoop on Jess and Tony’s relationship, pick up the new copy of OK! — on sale everywhere Thursday!

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