10. Christina Aguilera
While they were together, he toured with her and appeared in some music videos. Since they split amicably in 2001, they’re still supportive of each other, and Santos even follows Christina on Twitter.
9. R. Kelly
They had three kids together and she stayed with him through his child pornography charges and trial in 2007. They got divorced in 2009 after 13 years of marriage and Andrea has since appeared on the VH1 reality show Hollywood Exes.
8. Ashely Tisdale
They toured together for the High School Musical: The Concert and he appeared in a few of her her solo music videos as well, but they split in 2009. In 2014, Tisdale married musician Christopher French.
7. Melanie B
They had a daughter, Phoenix, but ended up filing for divorce only two years later. Gulzar blamed Mel’s breast implants and adultery for the split.
6. LeAnn Rimes
She and Sheremet divorced in 2009 after reports that she’d cheated on him with her Lifetime movie co-star, Eddie Cibrian. Cibrian divorced his wife of eight years as well, and he and LeAnn got married in 2011.
5. Geri Halliwell
She reportedly didn’t feel a strong enough spark and didn’t think the relationship was going anywhere. Halliwell is now married to Christian Horner, a race car drive for the Infiniti Red Bull Racing Formula One team.
Garcia was 22 and Prince was 37 when they got married on Valentine’s Day 1996. They had a son, born that October, but tragically, he was born with a rare skull defect and he passed away a week later. They got divorced in 1999, but Mayte has said “although I am not actively in love with him [Prince], I will always love him – he’s a great guy.”
They dated for three years before calling it quits. That wasn’t Madonna’s only young conquest. She also dated model Jesus Luz before Zaibat, and she split from another backup dancer, 26-year-old Timor Steffens, last summer.
2. Britney Spears
Their relationship attracted a lot of media scrutiny and was thought to be the beginning of Britney’s mental decline. Federline was awarded sole physical and legal custody of the boys, which he still has today.
1. Jennifer Lopez
Smart, who is 28, told People magazine, “we’re just being ourselves, just having a good time, that’s all,” when asked about their relationship status. And we can’t forget Lopez’s marriage to backup dancer, Cris Judd, which lasted less than a year.