TLC songstress and baby mother to producer Dallas Austin had a long-term relationship with baby face Usher Raymond.
The legendary R&B crooner was rumored to be boo-loving with Gerald Levert before his unfortunate passing. We see you, Miss Patti.
One-fourth of the 1990’s group X-Scape has been rapper TI’s ride-or-die chick for over a decade, and there is a six-year difference between the PDA-crazed lovers.
Has a rumored teenage daughter (which qualifies her as a MILF) and had a long relationship with Jermaine Dupri who is seven years younger than her.
No babies here, but this beautiful talented actress deserves an honorable mention in the category. She has been going strong with her NBA baller boo who is a decade younger than she is.