The 53-year-old "X Factor" judge who has dated many beautiful women but has refused to marry is reportedly expecting a baby with New York socialite Lauren Silverman.
The 36-year-old brunette is still married to one of Cowell's close pals, Andrew Silverman, who is a real estate mogul in New York City.
"Lauren and Andrew have been unhappy in their marriage for some time, and their divorce has been in the works for a while," a source said.
Lauren is said to be about two and a half months pregnant.
The X Factor judge and Lauren have been dating since late last year after Lauren's marriage to Simon's friend broke down.
Simon Cowell has been engaged twice; to model Louise Payne in 1995 and make-up artist Mezhgan Hussainy from 2010 to 2011 but has never been married.
The multimillionaire who once said he's not cut out to be a dad is finally going to be one.