Diddy's Relationship History: From Kim Porter To J.Lo

Sean Combs, aka Diddy, has gone by many names over the course of his career, but changing the moniker doesn't seem to change the man — the "I Need a Girl" hitmaker remains the same ol' admitted commitment-phobe.

Diddy can boast being a music producer, artist, and record label founder. But while he's learned how to build lasting professional relationships, he readily admits that mastering the art of the give and take required for a healthy romantic partnership is something that alludes him. "I've been successful in a lot of things, but I haven't been successful in the love area," he told The Guardian in 2010. "And that's not just me finding someone to love, that's me loving someone back and being mature enough to sacrifice and not be selfish." Yet, Diddy is ever the optimist. On "The Ellen DeGeneres Show" in May 2022, the rapper even said that Love is his middle name, revealing that he had it legally changed.

Diddy has also devised his own system for allowing himself some leeway to behave badly without completely ruining his relationships — in theory, at least. In an appearance on "The Breakfast Club," he confessed that he makes his romantic partners miserable 25% of the time by being unfaithful and untruthful. "But then there's 75% of, I'm gonna make you the happiest woman in the whole wide world," he added. Unfortunately for Diddy, applying this pizza pie version of amore to his relationships hasn't worked out so well for him.

Diddy met Misa Hylton-Brim before he was famous

In a 2017 appearance on "The Wendy Williams Show," Diddy made a surprising revelation about his children. At the time, he had fathered half a dozen kids with three women, per People. "I met all of them in the same year," he said of the moms. The first was Misa Hylton-Brim.

Diddy started dating Hylton-Brim in the early '90s while he was working as an intern in the A&R division at Uptown Records. She was just 17 years old, per Billboard, but she soon became a top hip-hop stylist after helping Diddy create a fresh new look for Jodeci, an R&B act he had been put in charge of developing. Record exec Andre Harrell was hesitant about her ideas at first, but after seeing her vision, he hired her to style then-up-and-coming artist Mary J. Blige. In addition to launching her fashion career, Hylton-Brim landed a role in The Notorious B.I.G.'s "Big Poppa" music video — that's her pictured above rocking the blonde space buns in the hot tub.

Hylton-Brim and Diddy welcomed their son, Justin Combs, in 1993, but the rapper was apparently not interested in being a family man. In a 2018 appearance on "The Premium Pete Show," Hylton-Brim said that Diddy's rising star doomed their relationship. "He wanted to experience life in a different way," she explained, adding, "He's becoming famous and rich really quickly. ... He wasn't ready to settle down and get married, and I think that's what I wanted."

It was love at first sight when Diddy met Kim Porter

Kim Porter caught Diddy's eye while he was still working in A&R at Uptown Records. She came in one day with her boyfriend at the time, musician Al B. Sure!, and Diddy told Essence that he was instantly smitten. "I was admiring her — her lips, her eyes, her mouth, her shape, her energy — and thinking, 'I wish I had a girl like that,'" he recalled. The infatuated intern got ample opportunity to obsess over Porter — and plead with her to go out with him — when she was hired as Uptown's receptionist, but she initially spurned his romantic overtures. "[Combs] was very determined. If he wanted something, he never let go until he got it," one of Porter's pals recalled to Page Six.

It was 1994 when Porter finally caved. While Diddy had just become a father months earlier, Porter was impressed by how well he got along with her toddler son, Quincy, whose bio dad was Al B. Sure!. Per Metro, Diddy eventually adopted Quincy, who would later follow in his father's footsteps by pursuing a music career.

Diddy and Porter spent all of their time together. "I'm talking about from a strip club to playing poker, she would be there," Diddy told Essence. The couple welcomed their first child together in 1998, another son they named Christian. A year later, Diddy disrupted their life as a happy family by falling for another woman: future mega star Jennifer Lopez.

He got arrested with J.Lo

Diddy was working on the music video for "If You Had My Love" when he first met Jennifer Lopez. At first, he seemed to believe that he could have J.Lo's love and a happy home life, but one of Kim Porter's friends caught wind of Diddy's infidelity. Porter remained stoic while the rapper and his new girlfriend made a splash. "I had just had a baby. I couldn't be somewhere in a corner heartbroken," she told Essence.

Diddy and J.Lo's relationship began with a bang. In December 1999, the couple was attending a party in NYC when Diddy was involved in an altercation that resulted in multiple people getting shot, per ABC News. The couple fled in Diddy's vehicle but ended up behind bars after being apprehended by police. Lopez was soon cleared of any wrongdoing, but it would be two years before Diddy was acquitted.

Before the flash-in-the-pan couple flamed out, they made an unforgettable appearance together at the 2000 Grammys. But it was Lopez's verdant Versace gown, not her date, that made her red carpet stroll so iconic. "I thought it was gonna really change the game as far as for her and fashion," Diddy told ET of the revealing look in 2017. After the couple split in 2001, Lopez told Vibe (via Entertainment Weekly), "It was the first time I was with someone who wasn't faithful. ... It really took my whole life in a tailspin."

Kim Porter took Diddy back

After his fling with J.Lo fizzled out, Diddy resumed his relationship with Kim Porter. In a 2006 Oprah Winfrey interview, he scored some brownie points with Porter by somewhat throwing Jenny from the Block under the bus. "I could never go forward and finish the relationship with Jennifer because I was still in love with Kim," he said. Diddy admitted that he found Porter's acceptance of his infidelity attractive but suggested that he was finished being unfaithful. "With Kim, I ain't got no more strikes," he sagely observed.

Luckily for Diddy, Porter believed that his romance with the "Love Don't Cost a Thing" singer didn't mean anything. She explained it to Essence by saying, "He just got caught up in the hype." She also said that Diddy called her constantly while he was with Jennifer Lopez, but she wasn't always in the mood to listen to his assurances that he would come back to her.

Diddy confessed to believing that Porter would change to fit his idea of what a partner should be if he fooled around with someone else, not realizing just how foolhardy of a plan this was. But in a 2007 interview with the Mirror, he painted a vivid picture of where his relationship with Porter was at while describing a trip to Paris. "We went up to my suite and had tantric sex for at least 30 hours, ordering up whipped cream and strawberries while we were at it," he recalled.

He got dumped after having a child with Sarah Chapman

In a 2010 interview with Power 105.1 radio host Cherry Martinez, Misa Hylton-Brim revealed that Diddy had an ongoing relationship with stylist Sarah Chapman that started back when she and Diddy were an item — and it apparently didn't end when he met Kim Porter. Gene Deal, one of Diddy's former bodyguards, suggested to "The Art of Dialogue" that Diddy possibly started pursuing Chapman because she had dated his rap rival, Tupac.

Speaking to Essence (via People) about the Diddy misdeed that finally sent her packing, Porter revealed that she was pregnant when she learned that her longtime partner had fathered a baby girl with Chapman. But it wasn't Diddy who informed her about the arrival. "I would have preferred to find out from him because that's a man," she said. Five months after Chance Combs was born, Diddy and Porter welcomed twin daughters D'Lila Star and Jessie James in December 2006. Porter sat on her knowledge and waited for Diddy to come clean, and he made his confession after she gave birth. "I was like, 'Dude, this is so wack I can't even respect you right now,'" she recalled. Porter ditched Diddy for good the following July.

In an interview with Sandra Rose, Chapman shared a theory about why Porter decided not to confront Diddy about Chapman's pregnancy. "She kept it a secret to herself so it wouldn't take the shine off of her," she suggested.

Diddy and Cassie's tumultuous relationship begins

After Diddy signed Cassie Ventura to his Bad Boy Records label in 2006, he became a mentor to the up-and-coming artist. At the time, he was busy hyping up his album "Press Play," telling i-D that it was loaded with love songs about Kim Porter. Meanwhile, Cassie was riding the wave of Myspace fame before the social network crashed and burned (with no assist from a certain Tesla founder). Her song "Me & U" found an ever-expanding audience on the platform in 2005.

Producer Ryan Leslie told the New York Daily News that Cassie, who was a model at the time, caught his eye at a club, and the two struck up a conversation about music. It was Leslie who wrote and produced her first hit, and he also orchestrated the internet campaign to bring it the masses. In an interview with Essence, Leslie revealed that he dated Cassie before Diddy did. "It's definitely affected our relationship," he said of the seemingly messy situation.

Cassie told The Urban Daily that Diddy heard "Me & U" at a club and set out on a mission to meet the artist behind the music, and by 2007, there were rumors that he and his protégé were an item. "They're holed up together in Miami, very low-key. He's really in love with her," a source cited by Page Six claimed. In 2008, G Style Magazine shared photos of the pair looking very much like a couple during an outing in Central Park.

A relationship confirmation and engagement rumors

Cassie and Diddy kept their relationship on the down low for years. But in July 2008, Cassie did tell reporters that she and the rapper had split up, per Us Weekly. In 2011, there were rumors that Diddy had moved on with "Charlie's Angels" star Cameron Diaz. However, reps for the actor and the rapper told the New York Post that their relationship was just a friendly one.

In 2012, Diddy and Cassie finally went public with their romantic relationship by declaring their love for one another on social media. "Been committed for a LONG time to someone and I am sooooo in LOVE with HIM!" Cassie wrote in an impassioned since-deleted Twitter post (via The Jasmine Brand). A few weeks later, Diddy shared a later-removed photo of Cassie on social media. "I'm a very lucky man #knowthat," he captioned it, per Vibe.

In 2014, the self-professed "Bad Boy for Life" had fans convinced that he was finally ready for a wife. Diddy shared a since-deleted photo of a huge diamond ring on Instagram and asked in the caption, "Baby do you like it? I just want to get you wat you Like!" However, his rep later told E! News that the post was not a marriage proposal, and in 2015, Diddy confirmed that he still wasn't ready for that type of commitment. He was, however, willing to compromise. "I will commit to a contract — a love contract," he said on "Watch What Happens Live" (via Page Six).

Gina Huynh and a Jennifer Lopez reunion

Cassie and Diddy really seemed to be heating up in 2015. When they appeared together in an ad for Diddy's fragrance 3AM, Style.com compared the steamy footage to "Fifty Shades of Grey," but the musician said, "That whole interaction has nothing to do with sex as much as it has to do with love."

However, it seemed that Cassie wasn't feeling the love when she posted and deleted an Instagram meme that December. It featured a photo of a peacefully napping baby and the words, "How I sleep knowing that I'm single and nobody cheating on me," as captured by The Shade Room. Sources cited by LoveBScott said that Diddy had been spending time with a model named Gina Huynh. Years later, Huynh told The Jasmine Brand that the cheating reports were true, but she said that she felt incredibly guilty about sneaking around with Diddy behind Cassie's back. "I apologized to her afterwards," Huynh stated.

According to Diddy, he also had some explaining to do when he was photographed having a good time with his ex, Jennifer Lopez, at a party in November 2015. On "The Breakfast Club," Diddy said that Cassie asked him about the pictures. However, he was able to assuage her concerns by saying that Lopez's boyfriend was also in attendance. He'd previously praised his ex's "Booty" music video — and the visuals in it — during a 2014 "Access" interview. "That thing right there is something special," he marveled.

A phone fight and the making of a Met Gala meme

In 2016, Diddy and Cassie reportedly got in a fight after she told him that she was dumping him. According to sources cited by TMZ, Diddy allegedly reacted by fleeing with Cassie's phone, apparently because he wanted to analyze her texts to see if he could discover why she was leaving him. Cassie's mom reported the incident to the police, but Diddy had returned the device by the time the cops showed up.

A few days later, Diddy smoothed things over with Cassie by throwing her a big birthday bash. "Diddy won't ever let Cassie get away. He loves her so much," an insider told E! News. Another source addressed rumors that Diddy temporarily stole Cassie's phone because he feared that she was being unfaithful. "Cassie would never cheat on Diddy, though. She just wishes things were better with them," said the insider.

The couple attended the Met Gala together the following year, and Diddy became a meme by lounging on the stairs while photographers continued snapping pictures of Cassie. "I was getting tired so I laid down on the stairs!!!" he later explained in a since-deleted Instagram post, per Just Jared. While photographs of that moment went viral, in an October 2017 interview with Power 106 Los Angeles, Cassie said that she and Diddy weren't really paparazzi magnets. "We've really been left alone. ... People really just let us chill, which is nice," she stated.

Cassie and Diddy call it quits

In October 2018, a rep for Cassie told LoveBScott that she and Diddy had broken up months earlier. The outlet claimed that Diddy had been spotted at a Drake concert with a model named Jocelyn Chew days before the split announcement, while a source who spoke to People insisted that Diddy was single at the time the breakup news broke. "This fling with Jocelyn will likely fizzle out," another insider predicted in an interview with Us Weekly.

Yet another source told Hollywood Life that Cassie was allegedly angry and hurt because she had believed that Diddy was finally ready to embrace monogamy. "The thing that she's most pissed about though is the fact that she's now 32 and single and has to start looking for a future baby daddy," the insider claimed. "Sean knew Cassie wants a baby, and he promised her they would have one together, but that's yet one more thing that never materialized." This time around, Diddy was also reportedly convinced that he was a victim of infidelity. Not long after he and Cassie split, she made her relationship with her personal trainer, Alex Fine, Instagram official. However, according to TMZ, sources close to Cassie insisted that their romance didn't blossom until after Diddy was out of the picture.

Diddy reportedly hired Fine, so in a roundabout way, he gave Cassie what she wanted — she and Fine got married and celebrated the birth of their daughter, Frankie, in 2019, per TMZ.

Diddy regretted not marrying Kim Porter

In November 2018, Kim Porter died from pneumonia. Diddy was devastated. "At first ... I cried for like three months straight," he later said on the "Caresha Please" podcast. "... It just hurt so bad." He got emotional while discussing the loss on Essence's "Yes, Girl!" podcast, noting that what made it even more heartbreaking was that Porter was being mourned by her children. "Anybody that's lost a mother or lost a soulmate, it takes time," he said. But Diddy then suggested that time won't heal the wounds caused by Porter's death.

While interacting with his Instagram fans in March 2019, Diddy expressed regret over not marrying Porter when he had the chance. "I wasn't ready and that's it. I'm ready now but it's too late," he wrote in response to a question about why he never popped the question, per XXL. When he appeared on Teyana Taylor's YouTube series "Luv2SeeIt" in October 2022, Diddy revealed that he realized just how special Porter was when he started rereading some of her text messages to him. "I was like, 'Yo, I hope I can find somebody that can love me like that again.' I'm not giving up on love, but it's hard," he said.

In an Instagram Live with Fat Joe, Diddy showed off a massive monument to Porter he had built in his yard: a mirrored statue of a woman's torso and thighs. While filming the back of it, he quipped, "My baby had a little badunkadunk!"

His rumored relationship with Lori Harvey

In August 2019, Diddy was romantically linked to Lori Harvey, the stepdaughter of "Family Feud" host Steve Harvey. This shocked fans, as Lori had supposedly dated Diddy's son, Justin Combs, in the past, per The Daily Beast. "Lori Harvey coulda had anybody and she chose Diddy," read one tweet about the alleged unexpected coupling. TMZ pointed out that Lori and Diddy were spotted wearing coordinating outfits in NYC and vacationing with Lori's family in Italy, but they never confirmed that they were together.

In September 2019, Diddy and Lori jetted off on another getaway to Cabo. "They swam together in the pool and wrapped their arms around each other to kiss. They had a candlelit dinner overlooking the beach," a witness later claimed to E! News. Upon their return, they sparked pregnancy speculation when Diddy was photographed rubbing Lori's stomach. However, sources later told TMZ that he was just admiring her washboard abs. That same month, The Shade Room posted a video of Lori and Diddy partying at the Magic City strip club in Atlanta with a surprising guest: Justin.

One of Diddy's other sons, Christian Combs, spoke to Hollywood Life about the romance rumors, and he seemed to confirm that something was going on. "They good. They're just being ... private time. That's up to them," he said. But sometimes, you just "Gotta Move On" — a source told E! News that Diddy reportedly decided he wasn't ready to commit, so they split in October 2019.

Diddy gets cozy with Yung Miami and Joie Chavis

In June 2021, City Girls member Yung Miami shared an Instagram photo of herself and Diddy holding hands, sparking relationship rumors. "The new power couple," one of her followers proclaimed in the comments. Yung Miami fueled the romance speculation further that August by posting a video to her Instagram Story that appeared to show her sitting in Diddy's lap, per Complex. But the following month, the Daily Mail published photos of Diddy kissing Joie Chavis, a model who has been romantically involved with Future and Bow Wow. (She also shares children with both rappers.) The smooch took place on a yacht in Italy. 

Bow Wow later spoke about the PDA on the "The Morning Show 107.5 WGCI," revealing that he reached out to Diddy and had a long conversation with him because he felt a bit wronged. "It's still a line of respect. ... I heard his piece, I heard her piece, they heard mine. And we just gonna leave it at that," he said.

The following year, Chavis expressed regret over the kiss. In response to a post on The Shade Room's Instagram page, she explained that she and Diddy had been in Italy for work and revealed that nothing else happened between them. "The kiss shouldn't have happened, but it did, and there's nothing I can do about it," she wrote, per MadamNoire. Chavis also said that she let Yung Miami know about it.

Yung Miami vs. Gina Huynh

During the Billboard Music Awards in May 2022, Gina Huynh used her Instagram Story to inform her followers that she was in the audience at the show. As Diddy spoke on stage, she filmed a video and captioned it (via The Shade Room), "Baby daddy is hosting Billboards." Huynh also shared a photo of Diddy kissing her cheek, according to The Jasmine Brand, and all hell broke loose.

Yung Miami seemingly saw the snapshot and fired off a barrage of tweets that appeared to be a response to it. "Notice me please a** b***h go sit down! WE SEE YOU RELAX IT'S ok! You been (AROUND) just (AROUND) for years! You been waiting on this moment if he can't make you famous b***h I ain't!" one tweet read. On her Instagram Story, Huynh fired back. One of her messages read, "Why you so press mama? I thought you was a city girl," to which Yung Miami replied, "I am and that's why I f*** with yo n***a & ain't coming off him idc how many pics you post!"

In her June 2022 interview with The Jasmine Brand, Huynh confessed that she didn't know exactly where she stood with Diddy, relationship-wise. "I've been with him for a very long time, but it was never set in stone." A few months later, Yung Miami told XXL that she and Diddy were seeing each other — and other people. "We single, but we're dating," she said. "We're having the time of our lives, but we're still single."

Diddy's daddy surprise

In December 2022, Diddy announced that he had welcomed his seventh child. "I'm so blessed to welcome my baby girl Love Sean Combs to the world. Mama Combs, Quincy, Justin, Christian, Chance, D'Lila, Jessie and myself all love you so much! God is the Greatest!" he tweeted. While Diddy did not disclose the identity of his daughter's mother, it was later reported that she is a cyber security specialist named Dana Tran.

DJ Akademiks reacted to the news by tweeting, "My N***a done f***ed around and had a side baby on his harem of side chicks." Yung Miami seemed to view this as a personal attack. "I'M NOBODY SIDE B***H LETS JUST MAKE THIS CLEAR ON THIS GOOD MONDAY! I don't come 2nd to no b***h!" she shot back. For his part, Diddy echoed this sentiment on his own Twitter account. "[Yung Miami] is not my side chick," he wrote. "Never has been, never will be. She's very important and special to me."

The baby drama didn't end there. Gina Huynh seemingly used the news to reignite her feud with Yung Miami, sharing an Instagram video that referenced their long-standing beef and Tran's pregnancy. When she fired back on Twitter, Yung Miami appeared to go low by making remarks about her rival that some of her followers deemed racist. This probably was not the reaction Diddy was hoping for when he decided to name his baby girl Love.