Sean Combs, popularly known as Puff Daddy or Diddy, is one of the most notorious rappers in the world of music. The legendary rapper has not only come out with some smash hits, but he's made a massive success with his own record label and fashion line.
Considering the level of Diddy's success, it's no surprise that he finds beautiful women on his arm time and time again. The rapper is not necessarily one to be super public about his relationships, but he's definitely had a few!
The rapper is not only a father to six kids with three different women, but he is known for dating some of the most beautiful models, actresses, and singers to this day. Although he isn't in a serious relationship right now, there's no doubt that he will be walking down the red carpet with someone soon. With that being said, here are 20 stunning photos of the women Diddy has dated.
20 Jocelyn Chew
Diddy has definitely dated his fair share of beautiful women, but it's not stopping anytime soon. The rapper is currently in an alleged relationship with the Canadian model and influence, Jocelyn Chew. The two have been spotted out together a few times, causing rumours to begin about their possible romance.
19 Cassie Ventura
Cassie Ventura is an absolute gem! The singer and actress, who dated Diddy for a whopping 11 years, is easily one of the most beautiful women Diddy has dated. The public was incredibly stunned when the two announced their split this year, causing many to speculate as to why.
18 Tracey Edmonds
Tracey Edmonds was notorious for dating actor Eddie Murphy, however, it appears the star also had a few rendezvous with rapper, P. Diddy! Although there was no official confirmation between either party, Edmonds and Diddy spent quite a lot of time together!
17 Cameron Diaz
Cameron Diaz is known for countless of her films, however, one thing that may surprise you is that she and big-time rapper Diddy, actually dated! The two were never exclusive but spent loads of time together. According to Daily Mail, Diddy wishes he had pursued a romantic relationship with Cameron Diaz and regrets not having snagged her when he should've.
16 Sienna Miller
British star Sienna Miller is yet another beautiful woman who dated Sean Combs. The actress reportedly dated the rapper back in 2007 and was spotted with him several times. Miller first made headlines connected to Diddy when she was spotted going into his hotel in New York City one night.
15 Emma Heming
Before Emma Heming was Emma Heming Willis, she reportedly dated rapper, Sean Combs. The two were seen out quite frequently in 2001, and sources claimed that the two were in fact dating. Although neither Heming or Diddy commented on these rumours, the evidence is there to back it all up.
14 Karrine Steffans
Author Karrine Steffans is another rumoured woman to have dated Diddy. Although it was all speculation, the two were "friends" and seen out quite a lot. They both met at a party in the early 2000s and introduced by a mutual friend. Reports claim that the two were glued to each other afterward, causing rumours to start.
13 Jennifer Lopez
Jennifer Lopez may be with baseball legend A-Rod now, but she once dated Diddy, too! Believe it or not, the 'Get Right' singer date Diddy in 2000 and they were the most talked-about couple for some time! The star even wore her iconic green Versace ensemble while dating the rapper, where the two walked the red carpet together.
12 Sarah Chapman
Sarah Chapman a well-known woman in the fashion world dated Diddy back in the 2000s. The two dated for months, and even share a daughter, Chance Combs, together. Additionally, the two were spotted hanging out this past August at a museum with all of Diddy's kids.
11 Misa Hylton-Brim
When it comes to love, it appears Diddy can move on real quick. Misa Hylton-Brim, a prominent woman in fashion, also shares a baby with Diddy. The two dated briefly and broke things off when Diddy met another woman. Believe it or not, but Diddy met all of his baby mamas in the same exact year!
10 Kim Porter
Speaking of baby mamas, Diddy and Kim Porter also dated right after the rapper broke things off with Jennifer Lopez. The two share four children together and had quite a strong relationship. The couple would attend numerous events together and have been photographed countless times during their years together.
9 Yasmeen Ghauri
Yasmeen Ghauri is a Canadian-born model who briefly dated Diddy in the mid-2000s. The two were never official according to reports and did not last long. Ghauri is not too well known today, but 15 years ago, she was one of the most beautiful models to strut the runway, and we all know how much Diddy loves his models.
8 Aubrey O'Day
Aubrey O'Day made her debut in the entertainment industry as a member of the girl group Danity Kane. O'Day met Diddy as he was the group's manager at the time. The two were romantic during this time, however, things didn't work out. O'Day has even gone on record blaming Diddy for breaking up the group, so it's clear they didn't end things on a good note.
7 Lori Harvey
Lori Harvey made headlines when she and Diddy dated over the summer, however, things didn't last. Lori, who was previously dating Diddy's son, is also the stepdaughter to Steve Harvey. She and Diddy lasted for a mere three months before calling it quits.
6 Naomi Campbell
Diddy, who is one of the biggest rappers in the world, has found himself Naomi, the biggest model in the world. This dynamic duo has conquered both their worlds, so it is no surprise that they'd find each other. Naomi and Diddy have been friends for quite a while, and recently attended an event together as "friends", however, many believe that there is more to the two than just that.
5 Penelope Cruz
Penelope Cruz and Diddy first met when she was featured as the face of his fashion line, Sean by Sean Combs. The two worked on the massive campaign together and have spent many times together, however, many believe that the two have mixed business with pleasure.
4 Lil Kim
Lil Kim and Diddy have had a very long friendship over the years. The two have been very close, and have been rumoured to have dated back in the 90s. The two rap icons, unfortunately, ended their friendship when Kim went to prison. The 'Catch My Wave' rapper claimed Diddy never visited her during her year-long sentence, which put a strain on their friendship.
3 Nicki Minaj
If it isn't a model, Diddy is going after a rapper. Nicki Minaj is amongst the numerous women who have been rumoured to date, Diddy. The two worked together on the "Hello Good Morning" song and became instantly close right after. In fact, the two became so close that the public began to question whether the two were more than just friends.
2 Keyshia Cole
Singer Keyshia Cole was featured on Diddy's song "Last Night". Although the two had been friendly prior to their collab, reports claim that Diddy and Cole both began a romantic relationship after they worked together on their song back in 2015.
1 Ingrid Vanderbosch
To finish off the list is someone you might not know, however, we've saved the best for last. Ingrid Vanderbosch is a model and actress from Belgium that was reported to be dating Diddy back in the 2000s. The couple was seen out a few times, however, it wasn't until Ingrid attended one of Diddy's fashion shows, and had an outburst! Vanderbosch ended up getting seated beside Kim Porter, who was also tied to Diddy romantically. The model got so upset that she caused a scene at the show and refused to be sat Porter, making headlines everywhere.