Ashlee Simpson & Pete Wentz

Despite having an uber-famous sister, Ashlee Simpson also made a name for herself in the entertainment scene. During her teenage years, she first appeared in television commercials until she landed a role in the family drama 7th Heaven. She then furthered her investment planning and launched a lucrative music career. Somewhere this time, she met Fall Out Boy band member Pete Wentz. They exchanged vows on May 17, 2008, at Encino, California. Months later, they gave birth to a son named Bronx.

On February 9, 2011, Ashlee filed for separation from Pete. According to him, his marriage with the singer-actress started to go downhill after his band went on hiatus in 2010. Nevertheless, the two have maintained a friendship and are co-parenting their child, who is now 6 years old. Ashlee went on to marry Evan Ross, while Pete is currently in a relationship with Meagan Camper.