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He actually encouraged it."A P Diddy insider also described Lopez as Diddy's "fantasy girl" and "the love of his life". Sean "Diddy" Combs revealed how his longtime girlfriend, Cassie, reacted to his reunion with his most-famous ex, Jennifer Lopez, at the 2015 American Music Awards in November, and like Us, she had many, many questions. She had some questions," he reiterated with a laugh. In an interview with Despite the rocky breakup, the multi-hyphenates have remained amicable, found love (multiple times! After their romance, Lopez was married to dancer Cris Judd from 2001 to 2003, followed by her high-profile engagement to Diddy, meanwhile, has been dating “Me & U" singer Cassie Ventura on and off since 2007.Apparently, sources are telling TMZ that it’s “only a matter of time” before the two music powerhouses take their relationship to the next level.Though the two are currently just close friends working on music together, Drizzy and J.19, 2016), Drake reportedly shut down West Hollywood hotspot Delilah, where he hosted his 30th birthday party earlier this year, for an intimate dinner with 20 other guests.Jennifer Lopez's daring, curve-baring dresses on the red carpet since she stepped into the spotlight in the '90s haven't just proved JLo likes to keep it glitzy; they've also put the various boy toys that have appeared alongside her throughout the decades to shame.Jennifer Lopez’s love life hasn’t exactly played out like a Nora Ephron movie, but it’s still hard to believe that she actually dated Diddy at one point in time in her life.Lopez got with Diddy at the tail-end of the ’90s, back when he was known to his millions of fans as Puff Daddy.

Jennifer Lopez and P Diddy have been spotted together in New York, fuelling rumours that they are rekindling their former romance.They were one of the most famous celebrity couples during the late 1990s, so fans were understandably excited to see Jennifer Lopez and P Diddy reunited at a party in November.However, the music mogul's girlfriend Cassie had a few questions about their friendly get-together.The Latina star went on to date former back-up dancer Cris Judd, who she later married but divorced less than a year later. ' Maybe it's a little fast but they were thrilled to see me smiling." After her divorce, Jennifer dated actor Ben Affleck and the two became engaged in 2002 but split in early 2004."I was in this relationship with Puff where I was totally crying, crazy and going nuts, and it really took my life in a whole tailspin," she told in 2013. She began seeing singer Marc Anthony and the pair went on to wed in June of the same year.