P. Diddy, one of the biggest rap names to come out of the 90s, has had quite a reputation when it comes to the women on his arm. For a long time, it seemed like the question every fan wanted to answer for was, "who is he dating now?" Despite how fans may have seen it, Diddy seemed to genuinely care for and love those he dated, including Kim Porter, whose death was devastating to all who knew her, including Diddy. He still remains friends with some, such as J-Lo, who was seen recently in a reunion with the rapper.
Diddy, who has been very active on his Instagram lately, is a devoted father and friend. So let's take a look back at a time before social media took over the world, when we relied on celeb magazines to see who was dating who.
15 Lori Harvey Was Rumored To Be A Girlfriend
While it was never actually confirmed, it was rumored that Lori Harvey may have dated Diddy. While their relationship would have been short-lived, the rumors came about after the two were seen wearing matching outfits while out together. They were also photographed at a restaurant seeming to be more than friends, but still... a rumor is a rumor.
14 P. Diddy And Cassie Ventura Didn't Come Out As A Couple Immediately
Interestingly enough, while Diddy met Ventura at the start of the 2000s, the two didn't come out as a couple for some years. Therefore, fans could only assume that the two were friends before anything romantic came about. What transpired over those two years is still a mystery.
13 They Waited Two Full Years Before Confirming Rumors
In 2012, the couple finally announced that they were, indeed, dating. While many may have suspected this was the case prior, there was really no solid proof to back it up. When the couple was out in public, they absolutely dazzled fans, looking sophisticated and classy in their cohesive attire.
12 Their Relationship Spanned Roughly A Decade
It's pretty much all but confirmed that both Diddy and Ventura were able to pull off any kind of look, and the two were magic when they entered a room together. So much so, that the magic lasted roughly ten years before the two finally called it splits. In 2018, Diddy was already moving on.
11 Diddy Was Quick To Move On After Their Breakup
While fans thought that this was a for-sure deal, it seems that not all was as it seemed in Diddy-Ventura land. Even though the two were together for an estimated ten years (it's unclear if they actually started dating shortly after meeting for the first time), it wasn't enough to keep the relationship going.
10 Cameron Diaz And Diddy Dated For Four Years
The next biggest relationship to hit the red carpet that year was the one that transpired between Cameron Diaz and Diddy. While Diaz has a list of her own celebrities (Diddy isn't the first musician to make the list), their relationship lasted a decent amount of time - four years.
9 Jennifer Lopez And Diddy Had A True 90s Romance
Perhaps one of the most favored matchups by fans was the one between Diddy and Jennifer Lopez. He and J-Lo stunned the crowd as one of the music's scenes most attractive couples at the time, and there was simply no stopping this pair once they hit the red carpet.
8 They Were One Of The Hottest Couples To Grace Headlines
Literally, fans gawked over the sheer perfection of a show that these two put on when they headed out in public together. J-Lo had quite the reputation, herself, for being able to shake it like nobody's business, and with Diddy's suave nature and rap king reputation, they were powerful, to say the least.
7 They've Both Moved On But Have Remained Friends
Although the two were hot and heavy from the 90s into the 2000s, the relationship simply didn't work out. They were both still early in their careers, especially J-Lo, who would continue to see success more than a decade later. Fans were saddened by the split, but hey, things happen.
6 Misa Hylton-Brim And Diddy Had And Early 90s Relationship
We're throwing it way back now. Misa Hylton-Brim was fairly well-known because of the fact that they did have a child together. Their relationship, while not the longest Diddy had, clearly meant a lot, as he was devoted parent to his son.
5 They Were Together From 1992 To 1995 And Have A Son Together
Despite the relationship between himself and Hylton-Brim ending, Diddy continued to be a presence in his son's life, who is seen much older in this photo. If there's one thing Diddy can't be knocked for, it's the fact that he still makes time to spend with his children, despite his career.
4 Diddy's Relationship With Kim Porter Was On And Off For Three Years
When most fans think of Diddy, though, it's his relationship with Kim Porter that comes to mind. The two were likely in one of the most serious relationships of Diddy's and did have it in mind to take things to the next level. The two were together for three years, 1994 to 1997.
3 They Had Several Children Together
Although they had never married, Diddy and Porter did have several children together. She made a huge impact on his life and he credits her for him now being a full-time parent, her last words to him being, "Puffy, take care of my babies." The love between the two was obvious.
2 Diddy Says Her Sudden And Tragic Death Was Devastating
After Porter passed on, Diddy claims he "snapped into mommy mode" and even had his son's phone disconnected until he could reach him in person to explain what had happened. Since then, Diddy has been a devoted father, carrying the spirit of Porter, and her compassion, with him.
1 Many People Paid Tribute To Her, Including Diddy
Diddy still thanks Porter to this day for her presence in his life and the fact that she loved him and his family so much. In an interview with CNN in 2019, Diddy said that her memory lives on in his spirit as well as his kids, according to the rapper, and that's something he'll never let go.
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