Diddy’s love life: Look back at his past relationships as he announces birth of seventh baby

Diddy’s hit Bad Boy For Life is arguably one of his best-known chart-toppers – and it seems the scandal-ridden rapper is determined to keep living that mantra.  

The 53-year-old brought to life the theme of his hit song yet again when he announced on Monday that he had secretly welcomed his sixth biological child – a daughter named Love Sean Combs – with a fourth woman.  

While the rapper didn’t reveal who the mother of the baby was, TMZ reported that Love’s birth certificate listed cyber-security specialist Dana Tran, 28, as her mom.

The news sparked a slew of questions surrounding Diddy’s love life, as it comes just weeks after he was spotted holding hands with influencer Shawntya Joseph, and months after rapper Yung Miami claimed she was ‘dating’ the musician.

The 53-year-old’s dating history has certainly been a rollercoaster of a ride. He’s had six biological children with four different women over the years – and adopted a seventh – and his relationships have been filled with allegations of cheating, claims of multiple infidelities, and even accusations of abuse. 

In addition, a model that Diddy dated in 2019 claimed he paid her $50,000 to get an abortion after she became pregnant not once, but twice during their short-lived romance.

The music producer has also been linked to a slew of famous faces over the years, including supermodel Naomi Campbell, actress Cameron Diaz, Steve Harvey’s daughter, Lori Harvey, and singer Jennifer Lopez – who later called their whirlwind romance ‘crazy and tumultuous’ and said it ‘ended in a bang.’ 

Diddy, whose real name is Sean Combs, faced heartbreak in 2018, when his ex-girlfriend Kimberly Porter passed away from complications related to a pneumonia diagnosis.

He later admitted that the tragic lost left him ‘crying’ for ‘weeks,’ while calling Kimberly ‘more than his soulmate’ in a touching Instagram post.

As the star announces the birth of his seventh child, FEMAIL has taken a look back at his wild dating history. From the cheating and abuse allegations that rocked his romances to his four baby mamas and other exes, here’s everything we know about Diddy’s relationships.

Diddy dated stylist Misa Hylton-Brim in the early ’90s, and she gave birth to his first son, Justin, in 1993

Diddy dated a stylist named Misa Hylton-Brim from September 1992 to March 1995, and together, they welcomed a son, named Justin Dior, now 28, in 1993. 

It’s been reported that Diddy and Misa – who has styled celebrities like Lil’ Kim and Mary J. Blige over the years – stayed on good terms following their split, and have co-parented amicably.

In an interview years later, Misa accused Diddy of ‘cheating on her’ during their three-year romance, but made it clear that there were no hard feelings.

At the time, she said she ‘got along’ great with his other baby mamas, and that she was even close friends with Diddy’s then-girlfriend, Kimberly.

‘He was cheating on me but this is over 15-16 years ago,’ she said. ‘I joke around sometimes and say “[his baby mamas] are like my sister-wives.” I try to keep everything good.

‘I have love for him and he’s my family and I’m going to always support him and have his back.’

In September of 2012, Diddy proved they still had a cordial relationship when he shared a snap to Instagram of him and his ex spending time together at their son’s football game.

He was in an on-and-off relationship with Kimberly Porter from 1994 to 2007, and they welcomed three kids together

Soon after his relationship with Misa came to an end, Diddy started dating fashion designer Kimberly. They first met when she was dating singer Al B. Sure, and Diddy ran into them at the studio.

‘The first time I saw her, she was at the studio with her ex-boyfriend,’ he previously told Essence. ‘I wasn’t trying to holler at her or anything, but I was admiring her – her lips, her eyes, her mouth, her shape, her energy – and thinking, “I wish I had a girl like that.”

‘She kind of made me nervous. She wasn’t like a New York girl. She was Bohemian, mixed with Georgia-peach hospitality. 

‘I got the idea she’d like doing stuff like walking barefoot in the grass. I didn’t think I could get her to like me. She was smooth, you know, like ice. 

‘She’s cool and collected and thinks before she speaks. You meet a lot of young ladies, and they just don’t do that. Kim was never pressed; she was always in control.’

Kimberly and Al B. Sure eventually split, and she started dating Diddy soon after. They welcomed a son together, named Christian Casey, now 24, in 1998. Diddy also adopted her son from a previous relationship, named Quincy, now 31. 

But in 1999, they announced that they were ending their relationship – and the two became embroiled in a nasty custody battle over the then-one-year-old. In the end, they were granted joint legal custody.

However, four years later, the couple got back together. She then gave birth to their twin daughters, D’Lila Star and Jessie James, now 15, in 2006. But one year after that, the pair went their separate ways once again.

Kim sadly passed away at age 47 from complications related to pneumonia in November 2018, and afterwards, Diddy called her death a ‘nightmare,’ while referring to her as ‘more than his soulmate’ in a touching Instagram post.

‘For the last three days I’ve been trying to wake up out of this nightmare. But I haven’t,’ he wrote. ‘I don’t know what I’m going to do without you baby. I miss you so much. 

‘We were more than best friends, we were more than soulmates. WE WERE SOME OTHER S**T! And I miss you so much.’

He also later explained how losing his ex and becoming a single father to their kids forced him to ‘change’ the way he was ‘thinking.’

‘I had to really get focused on their futures because I know how rough it is out there,’ he said.

Diddy also said on Yung Miami’s podcast that he ‘cried for three months straight’ following her passing. 

‘I would just be walking around crying, just like all the time. It hurt so bad. I just didn’t … I was just not moving. I had isolated myself,’ he admitted.

‘It was rough. I really could not control crying. I would be anywhere and any memory would just get me and really break me down.

‘But as time went on and I had to deal with the reality and really prayer and God, talking to God is what got me through it. I had a wonderful life in time with Kim. 

‘I have beautiful kids and I’m just like the luckiest man in the world. To even have had the experience to have her in my life … it’s a daily thing though. I’m back up on my feet and I’m ready to love again.’

During his break with Kimberly, Diddy had a brief romance with Jennifer Lopez – after the two bonded over their love of music

During his break from Kimberly, Diddy was linked to a few other women – including actress and singer Jennifer, who he started dating in 1999.

The Jenny from the Block songstress later opened up about their romance, calling it a ‘kind of a crazy, heightened time in her life.’ 

According to Jennifer, they bonded over their love of music, and Diddy quickly became like a ‘mentor’ to her.

‘You know, Puffy and I both grew up in the Bronx,’ she said. ‘He had been in the music business and had all this success. I was just starting and making my first album when I met him.

‘He became kind of a mentor to me in that moment. We had this kind of crazy, tumultuous relationship that ended in a bang.

‘It was definitely a moment but I felt like it was necessary. He was meant to be in my life at that moment to teach me what I needed to know about the music business, about what kind of artist I wanted to be in the music industry.’

They were together for two years, before splitting in 2001. She later said she ended things because she didn’t feel like she could have the family life that she dreamed of with the musician.

He was also linked to Naomi Campbell and Cameron Diaz in the early 2000s, and welcomed his sixth child with a third baby mama named Sarah Chapman

After that, there was some brief speculation that Diddy was dating supermodel Naomi – after they appeared on the cover of British Vogue together – but that relationship was never confirmed.

He also dated a woman named Sarah Chapman in the early 2000s during his break from Kimberly. He and Sarah welcomed a daughter, named  Chance, now 16, in 2006, but went their separate ways soon after.

It appears that he and Sarah are on good terms, as he shared a sweet video hanging out with her and their daughter to Instagram in 2020.

‘I want to talk to y’all about the importance of long-term relationships. When you’re co-parenting, y’all gots to be friends,’ he captioned it.

‘To all the baby mamas and baby daddies, there just gotta be a time when the bulls**t stops and y’all can just laugh and y’all can chill. I’m blessed to have three of the greatest baby mothers on the planet. This is one of them right here.’ 

In addition, the exes were seen celebrating their daughter’s 16th birthday together back in July. 

There were also rumors that Diddy hooked up with actress Cameron following his split with Kimberly – but very little is known about their alleged fling.

Diddy was in a relationship with Cassie Ventura for over a decade from 2007 to 2018

Diddy started dating singer Cassie Ventura in 2007, after she modeled for his clothing line – but they kept their romance hidden from the public until 2012, when they attended their first red carpet event side by side.

They were together for more than a decade – until she reportedly left him in 2018 because he didn’t want to get married. 

Cassie quickly moved on with her personal trainer Alex Fine, and TMZ reported at the time that Diddy felt ‘betrayed’ as he suspected that Cassie had cheated on him with the gym buff, who had been working with Cassie for a year prior.

However, sources close to Cassie later told the outlet that Diddy’s ‘timeline is wrong’ and the pair ‘did not start dating until after she broke up with Diddy.’ 

By June 2019, all the tension seemed to be behind them as Diddy sent a congratulatory message to Cassie and Alex after they announced that they were expecting their first child together. 

‘Congratulations Cassie and Alex. I wish you all nothing but love and happiness. God bless,’ he said in a social media post. 

The musician later addressed his romance with Cassie in his song Gotta Move On, which came out this past June.

‘You found a new man, so I gotta move on. Guess you got a new agenda, with someone you barely know. I won’t, say you’re wrong. Guess you had to move on,’ the lyrics read. 

He also thanked his ex ‘for holding him down in the dark times’ while accepting an award for the song that same month.

Diddy was briefly linked to Gina Huynh in 2019, but she later accused him of physical and mental abuse

Diddy was spotted hanging out with model Gina Huynh soon after his split from Cassie. But after the relationship fizzled out in late 2019, Gina accused Diddy of ‘mental, emotional, and physical abuse’ in an explosive interview with Unwine With Ashak.

She alleged that he ‘mushed her face really hard’ and made her ‘nose bleed’ and threw her high heels at her. She also claimed that the music producer paid her $50,000 to abort a pregnancy two times throughout their short-lived romance.

She also said that he often compared her to his ex Cassie, stating, ‘He was mentally, emotionally, and physically abusing me. He would always compare me to Cassie and tell me that I’m the bad one, and she’s a good one.’

In 2022, she sparked reconciliation rumors when she posted a snap of him giving her a kiss on the cheek to her Instagram Stories. At the time, Diddy’s new girlfriend Yung Miami responded by writing, ‘Somebody, please give this girl some attention.’

‘He’s just a really good longtime friend of mine, nothing more, nothing less. I just want him to be happy, I want him to live his truth whatever that means to him. I don’t want to control him … I truly want him to be happy,’ Gina said in an interview afterwards.

‘At the end of the day, I really value the friendship that him and I have. I don’t really care to be his girlfriend … He did bless me in a lot of ways. I’m always going to be forever grateful and respect him.’

She also claimed that their relationship started while he was still with Cassie, adding, ‘He was so charming. I was young too. I was young, naïve, I didn’t know no better. It was enticing. It was very tempting. It was hard not to … I do feel bad though.’

The rapper was spotted cozying up to Steve Harvey’s daughter Lori in late 2019, but that quickly fizzled out

Many people wondered if Diddy was dating Lori in late 2019. The two were seen spending time together on numerous occasions, and they even jetted off to Italy and Mexico together. 

Neither spoke out about the romance publicly, but it seemed to be short lived, as the model unfollowed Diddy on social media after he started spending time with another woman.

After that, there was brief speculation that he was in a relationship with a woman named Miracle Watts, after they attended his New Year’s Eve party together in 2020. 

He recently confirmed he was dating model Yung Miami, but she said she was ‘no one’s side b***h’ after he announced he had welcomed his seventh baby

In June 2021, Diddy sparked romance rumors with rapper Yung Miami when the two were spotted holding hands at a party. One year later, Diddy confirmed they were ‘dating’ during an appearance on her podcast. 

At the time, he called her one of the ‘realest people he has ever met,’ and explained that while they have ‘great times’ together, he still considered himself ‘single.’ 

‘I’m single… but I’m dating. I’m just taking my time with life,’ he said at the time.  

‘Alright. So what we is?’ she then asked him, to which he replied, ‘We’re dating. We go have dates. We’re friends, We go to exotic locations. We have great times.

‘You’re like one of the realest people I’ve ever met and you’re authentically yourself. You’re a great mother and a great friend. We just have a good time.’

Back in September, she spoke about their complicated relationship to XXL magazine, explaining, ‘We are dating. We single, but we’re dating. 

‘People don’t know what dating means. He’s single, I’m single, but we’re dating. That’s what I mean when I say we go together.

‘When we’re together, we’re together. We’re having the time of our lives, but we’re still single. He see other people outside of me and I see people outside of him. I’m young. I’m dating. I’m, you know, having fun. I’m doing me. He’s doing the same thing.

‘I can’t speak for exactly what he doing or who he seeing, but we single and we dating. But we are dating each other, but we single. 

‘I think it just went over people’s heads, you know? People just like to take whatever they wanna take from.’

Two months later – in November – she revealed via Instagram that Diddy had sent her hundreds of stunning red roses, which practically filled her living room.

However, after the artist announced he had welcomed his seventh child earlier this month, Yung went on an explosive Twitter rant, in which she stated that she is ‘no one’s side b***h.’

‘I’M NOBODY SIDE B***H LET’S JUST MAKE THIS CLEAR ON THIS GOOD MONDAY! I don’t come second to no b***h,’ she wrote.

‘Diddy won’t even look half of y’all b***hes way!’ she continued. ‘Majority off y’all praying upon a falling star b***h please.’

Diddy was seen holding hands with Shawntya Joseph weeks before her announced the birth of his seventh baby 

Just weeks before he announced the birth of his seventh baby, Diddy was seen holding hands with influencer Shawntya.

The two were seen cozying up during a late night New York City stroll on October 19.

The pair looked smitten as they strolled along, staring into one another’s eyes and taking a moment to chat in the street.

The social media star – who boasts more than 100,000 followers on Instagram – is said to be a Southern California native, but it is unclear how she and the musician met and the extent of their relationship. 

Diddy cut a casual figure in a black puffy jacket and dark pants, as he held hands with his companion.

Shawynta, for her part, looked chic in a black top and leather trousers, paired with chunky boots and a bucket hat.