Sean "Diddy" Combs' most recent split from Cassie Ventura in 2018 was a shock to many fans as the two had an on-and-off relationship for a whopping 10 years. But, before he and the "Me & U" songstress would start their whirlwind romance in 2012, Diddy was known to have been linked to numerous female celebrities.

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The Bad Boy mogul dated and was rumored to have relationships with many women in Hollywood. From his infamous relationship with Jennifer Lopez in 2000 to his flings with Cameron Diaz and Sienna Miller, this rapper has a pretty impressive dating history.

10 Jennifer Lopez

One of Diddy's most famous relationships would be with "Love Don't Cost A Thing" songstress Jennifer Lopez, who he dated back in 1999 until 2001. The power couple would be spotted on several red carpets, with the 2000 Grammy's one of their most iconic moments, especially when J.Lo would wear that famous green Versace dress.

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The couple broke up in 2001, after Lopez admitted during an interview with Oprah Winfrey that Diddy was not interested in settling down and having a family like she wanted.

9 Aubrey O'Day

Aubrey O'Day met Diddy when she was a part of the girl group Danity Kane, which was formed by the rapper on his MTV reality show Making the Band in 2005. Danity Kane saw major success in the U.S., and it was rumored that Diddy was romantically linked to O'Day at the time.

However, the two would have a rocky relationship and during the series, she and her bandmate, Wanita D. Woods were removed from the band in 2008. O'Day would go on to say some very unpleasant things about Diddy later on.

8 Sarah Chapman

Diddy and Sarah Chapman had a short-lived relationship, even though he would end up fathering one of her kids, a daughter named Chance, in 2006. At the time, he was romantically involved with model Kim Porter, who would also have Diddy's twin's in the same year named Jessie James Combs and D'Lila Star Combs, according to People.

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Chapman and Diddy seemed to put their pasts aside for the sake of their children when in 2019, they were spotted hanging out at a museum with daughter Chance, his twin daughters, and his son, Christian, whom he also shares with the late Porter.

7 Misa Hylton-Brim

Misa Hylton-Brim and Diddy knew one another since she was a teenager. Diddy was working as an A&R intern for Uptown Records and Brim was working as a stylist for his group Jodeci, according to CheatSheet.

In 1995, the pair welcomed a son named Justin, and their split did not end well at the time, with Brim wanting more money in child support. However, they remain on good terms today and are co-parenting their son.

6 Sienna Miller

In 2007, multiple photographs emerged of British model Sienna Miller partying with Diddy. According to TMZ, the rapper, who just welcomed newborn twins with model Kim Porter, was spotted dropping off Miller at her NYC hotel, sparking romance rumors.

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It seemed to be a short-lived romance as well, with neither of the stars confirming or denying that they ever had a relationship.

5 Cameron Diaz

The Bad Boy mogul and actress Cameron Diaz were rumored to have dated from 2008 until 2012, but after their relationship failed to succeed, Diddy admitted that he regretted not pursuing a more serious relationship with Diaz, according to Us Weekly.

Sources claimed to hear Diddy say during dinner about the actress, "If I could turn back time, things would be different!" However, Diaz had already moved on from the rapper and was dating then-boyfriend Benji Madden.

4 Tracey Edmonds

Rumors swirled around Hollywood that Diddy was dating producer Tracey Edmonds back in 2008. Edmonds had previously been married to comedian Eddie Murphy, and after their split, tabloid reports stated that she was quoted saying that Diddy was "the man for me."

However, Edmonds would go on to shoot down those rumors, with her rep stating that they were "a complete fabrication."

3 Kim Porter

One of Diddy's most serious relationships was with model Kim Porter, who he dated throughout the '90s, and welcomed his first child with named Christain in 1998. The pair broke up in 1999, but reconciled in 2003, and welcomed twin daughters in 2006, according to People.

While they never married, the two split for good in 2007, when a year before, Porter would find out that he fathered another child with Sarah Chapman. Sadly, Porter died in 2018, with Diddy later revealing that he "played himself" for not marrying the model.

2 Cassie Ventura

Diddy and Cassie Ventura had an on-and-off relationship for 10 years before they officially split in 2018. They were Hollywood's power couple, but it seemed that Diddy was still not ready to settle down with the songstress.

Ventura would end up leaving the rapper for her personal trainer, Alex Fine, who Diddy hired for the singer while they were together. However, she admitted there was no overlap and she and Diddy were already broken up.

1 Jocelyn Chew

After splitting with Cassie Venture for good, Diddy was rumored to be dating model Jocelyn Chew for a short time at the end of 2018. She seemed to be the rapper's "rebound" after his highly publicized split from the songstress, but by the new year, the two were no longer a couple, according to Page Six.

Currently, it appears that Diddy is single and enjoying every minute of it.

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