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Diddy’s Dating History: Who is He Dating Now?

Who is Sean Combs, also known as P Diddy, Puff Daddy and Diddy, dating now?

The New York Native rapper, actor, producer and record executive Diddy’s dating history includes many different relationships with women in the fashion and modeling industry, and music business.

Diddy rose to fame in the 1990s and today has reached massive success with his own fashion line and record label, Bad Boy Records.

Sean Combs, P.Diddy
FILE – In this May 30, 2018, file photo, Sean Combs arrives at the LA Premiere of “The Four: Battle For Stardom” at the CBS Radford Studio Center in Los Angeles. Combs has pledged $1 million to a network of charter schools for a new location in the Bronx. (Photo by Willy Sanjuan/Invision/AP, File)

Diddy Combs has been romantically linked to Yung Miami, Naomi Campbell, Jennifer Lopez, Lori Harvey, Sarah Chapman, Cameron Diaz, Cassie Ventura, Lil’ Kim, Misa Hylton Brim, Gina Huynh, Miracle Watts, Kate Upton, Emma Heming Willis and more.

Who is Diddy Dating Now?

Yung Miami and Diddy
Yung Miami has fans questioning over her current relationship status with Diddy after the rapper raves over her friends settling down. Photo:@yungmiami305/Instagram

Yung Miami (2021-present)

Diddy Combs and Miami Native rapper Yung Miami have been in a relationship since 2021. The Miami Native who is one-half of the rap duo City Girls confirmed her relationship with Puff Daddy in an interview with XXL on September 26, 2022.

Sean “Diddy” Combs and the Miami rapper also recently announced they were in a relationship during the first episode of her new show “Caresha Please.”

“We are dating,” Yung Miami explained. “People don’t know what dating means,” she added. “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.”

Since Sean “Diddy” Combs began dating Yung Miami in early of 2021 they are both set on keeping things casual and moving at their own pace.

“We date. We’re dating. We go have dates, and we’re friends. We go to exotic locations, we have great times, we go to strip clubs, church…” said Diddy Combs about his relationship with the Miami rapper.

Diddy Combs hasn’t provided much detail about his relationship with Yung Miami rapper since Combs praised her with thoughtful ‘Go Papi’ signs Miami made for Combs at the 2022 BET Awards.

Diddy Dating Timeline

Lori Harvey (2019)

One Fan Isn't Buying the Rumor That Sean 'Diddy' Combs and Lori Harvey are Dating, Offers Alternative Reason 
Some believe that Sean “Diddy” Combs and Lori Harvey are an item. (Photo: Getty Images, Rich Polk / Dimitrios Kambouris

Sean Diddy Combs and model Lori Harvey were rumored to be dating in 2019.

Lori Harvey, the daughter of Steve Harvey, sparked dating rumors with Puff Daddy, the record producer, in July 2019 when she and Sean Diddy Combs were spotted spending time together.

Diddy even joined Lori Harvey on a romantic getaway to Italy with Marjorie Elaine Harvey, the wife of Steve Harvey.

Sean Combs and Lori Harvey’s relationship was never confirmed publicly and didn’t last long after they split in 2019 when Lori Harvey unfollowed the rapper on social media.

Christian Combs, Sean Combs son, spoke publicly about his father’s relationship with Lori Harvey, saying: ‘They [are] good. They’re just being… private time… that’s up to them.’

Diddy and Lori Harvey apparently split in October 2019.

Gina Huynh (2019)

Gina V Huynh attends the Pre-Grammy Brunch
LAS VEGAS, NEVADA – APRIL 02: Gina V Huynh attends the Pre-Grammy Brunch & Surf Club Label Launch Celebrating Hit-Boy at the Lavo Restaurant at The Palazzo Las Vegas on April 02, 2022 in Las Vegas, Nevada. (Photo by Johnny Nunez/WireImage)

Puff Daddy and Gina Huynh were spotted cozying up together in summer of 2019.

Things took a sharp turn when Diddy was spotted with Cassi Ventura, his ex at the time, despite having ended things with Ventura.

Gina Huynh and Diddy’s romance was short-lived. Allegations were spread reporting that Diddy allegedly paid Huynh $50,000 to have abortions on two separate occasions.

Rumored Relationships

Shawntya Joseph (2022)

Shawntya Joseph @shawntyaaaaa/Instagram

Right before the end of the year, in December 2022, news broke that Diddy was spotted with Instagram model Shawntya Joseph.

Joseph, whose mother is Guyanese and her father is Panamanian, is a fashion designer and online personality.

Diddy and Joseph were caught by paparazzi who snapped photos first published by The Daily Mail, cozying up together walking the streets of New York.

Miracle Watts (2021)

Diddy began dating model Miracle Watts after rumours spread of the two together when Miracle Watts commented on Diddy’s Instagram post.

On April 3, 2021, the Bad Boy Entertainment founder posted a picture of himself shirtless with water dripping from his abs with the caption “Welcome to the LOVE ERA” while tagging “Off the Grid” as the location.

Miracle Watts responded to the steamy IG post by admitting in the comment section “GEEZZZZ!” adding two smiley faces with heart eyes emojis to further express her feelings.

Sources claimed that Miracle Watts and Diddy went on vacation with DJ Khaled to work on new music.

Neither Diddy or Miracle Watts has confirmed the dating rumors.

Diddy and Kim Porter Shared Three Children

Diddy Finds Buyer for Home Where Ex-Girlfriend Kim Porter Died Three Years Ago
NEW YORK CITY, NY – SEPTEMBER 16: Kim Porter and Sean Combs attend “Fashion For Relief” Sponsored by M.A.C Cosmetics at The Tent at Bryant Park on September 16, 2005 in New York City. (Photo by Joe Schildhorn/Patrick McMullan via Getty Images)

Sean ‘Diddy’ Combs and Kim Porter dated from May 1994 to July 2007. After Diddy and began dating Kim Porter in the 1990s, in 1998 the couple welcomed their first child together — a son named Christian Casey.

Following the couple’s breakup in 1999, a lengthy legal battle was carried out in court over their first child.

Diddy dated Jennifer Lopez for two years before reconciling his relationship with Porter in 2003.

In 2006, Diddy Combs and Porter welcome their second and third child together, twin daughters D’Lila Star and Jessie James.

Diddy
BEVERLY HILLS, CA – NOVEMBER 21: Model Kim Porter and recording artist Sean ‘Diddy’ Combs attend Sean “Diddy” Combs’ Exclusive Birthday Celebration on November 21, 2015 in Beverly Hills, California. (Photo by Allen Berezovsky/Getty Images)

At the time, Porter also had another son with music producer and singer Al B. Sure! Al B. Sure! and Porter had a child together, a son named Quincy Brown.

At 3 years old, Sure! and Porter’s son Quincy began being raised as if he were Diddy’s son, per the request of the rapper, who welcomed him into his family.

Diddy and Porter finally broke up in 2007. Tragically, Kim Porter died of pneumonia in November 2018, with Combs since then caring for their twin daughters D’Lila Star and Jessie.

Sean Diddy Combs welcomes a child with Sarah Chapman

I?m Giving You Your Flowers': Diddy's Appreciation Speech Stumbles When His Ex Sarah Chapman Thinks He?s Talking About Their 16-Year-Old Daughter, Chance
Diddy (L) and Sarah Chapman (R). Photo by GC Images/GC Images, @callmepumpkin/Instagram

While Sean Diddy Combs was building his career in the early 1990s, he also had his eye on a few women. Diddy Combs began dating Sarah Chapman in the late 90s and by the early 2000s, the two welcomed their first child together, Chance Combs.

Chance Combs was born shortly before Diddy welcomed daughters D’Lila and Jessie.

The world almost got a Sarah Chapman Diddy but their romance didn’t last much longer after Chance Combs’ birth, although Chapman kept her relationship with Diddy out of the public eye.

Years later, Chapman also mourned the loss of Kim Porter.

“Rest in paradise Kim, and know your kids are covered in prayer and love,” she wrote on Instagram.

“Your light will always shine thru your children and the way they all love each other is a blessing beyond words.”

High School Sweethearts Diddy has a son Justin Combs with Misa Hylton Brim (1990s)

Diddy met designer and stylist Misa Hylton Brim back in high school. The two quickly became high school sweethearts, and Diddy had his first son with Misa Hylton Brim, Justin Combs, in 1993.

Since then, they have co-parented their son Justin Combs together.

In 2018, Diddy’s exes paid tribute to Kim Porter after her death.

“Kim, for the last 20 years we have raised our children together, my mind cannot begin to wrap around the fact that you are not going to be here,” Misa wrote after Porter’s death, People reported.

“Thank you for being a 2nd mother to Justin and for loving Niko and Madison just the same,” she added, referring to her children from another relationship.

Diddy recently announced he is the new father to an infant daughter, Love Sean Combs, but he did not reveal the mother’s identity.

Star-Powered Relationship with Jennifer Lopez (1999-2001)

diddy and jennifer lopez
Diddy addressed his viral throwback image of himself and his ex Jennifer Lopez during a new interview with Vanity Fair. Photo:@diddy @jlo/Instagram

While the American rapper took a break from his relationship with Kim Porter, he dated Jennifer Lopez in 1999. Jennifer Lopez dated the Bad Boy Records rapper from 1999 to 2001.

Speaking to “The Breakfast Club,” Lopez later said that era of her life was “kind of crazy” and a “heightened” time. Diddy Combs and Jennifer Lopez first bonded over their shared upbringing.

“The Puffy era was just kind of a crazy, heightened time in my life. You know, Puffy and I both grew up in the Bronx,” said JLo about her initial attraction to the American rapper.

“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,” she added.

Puff Daddy and Jennifer Lopez called it quits by announcing their split on Valentine’s Day in 2001.

Later on, JLo opened up in an interview about the reasons behind the Diddy split. In the interview, Lopez said she would never have the family life she wanted with the rapper.

Plus, who can forget the drama of the December 1999 nightclub shooting that saw Puff Daddy and J.Lo arrested before she was quickly cleared of all charges.

Naomi Campbell (2001)

She's My Child': Naomi Campbell Shares Full Look at Her Daughter, Clear Up Speculations Surrounding Her Birth
PARIS, FRANCE – JANUARY 21: (EDITORIAL USE ONLY – For Non-Editorial use please seek approval from Fashion House) Naomi Campbell attends the Dior Homme Fall/Winter 2022/2023 show as part of Paris Fashion Week on January 21, 2022 in Paris, France. (Photo by Kristy Sparow/Getty Images)

Who can forget when Sean Combs dated legendary model Naomi Campbell in 2001?

Dating rumors of Sean Combs and Naomi Campbell began to circulate when they were photographed together in 2001 for British Vogue.

At the time, sources claimed that the romance carried on until 2002 but Sean Combs and Naomi Campbell never confirmed their relationship publicly.

After dating rumors died down, things remained platonic with the two.

Sean Diddy Combs falls for actress Cameron Diaz (2008-2012)

Sean Combs also dated actress Cameron Diaz from 2008 to 2012. Their romance began as a short-term fling when Puff Daddy and Diaz first hooked up in 2008.

Four years later the two were spotted together at the CAA gala in West Hollywood but soon after called things off in 2012.

The On-Again, Off-Again Relationship Cassie Ventura (2007-2018)

I Left Bad Boy': Cassie Talks Going Independent Following Her Breakup with Diddy and Whirlwind Marriage to Alex Fine
Cassie Ventura and Sean “Diddy” Combs attend the Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala at The Metropolitan Museum of Art on May 7, 2018 in New York City. (Photo by John Shearer/Getty Images for The Hollywood Reporter)

Diddy dated American artist and model Cassie Ventura from 2007 to 2018. Over the course of a decade, the two shared an on-and-off romance that was kept secret until 2012.

Though most of Diddy’s kids came from his relationship with Kim Porter, rumors in 2014 surfaced that Diddy and Ventura were married after Cassie Ventura was spotted wearing a sparkling ring.

Caresha Be Careful':?Fans Issues Warning to Yung Miami After Yung Joc Shares Personal Details About Diddy and Cassie's Relationship That Involved a Shaved Head
NEW YORK – NOVEMBER 20: Singer Cassie attends the Sean “Diddy” Combs’ Birthday Celebration Presented by Ciroc Vodka at The Grand Ballroom at The Plaza Hotel on November 20, 2009 in New York City. (Photo by Jemal Countess/Getty Images for Bad Boy Entertainment)

The two are believed to have called it quits between 2015 and 2018 before reuniting for the last and final time in October 2018. Sources at the time claimed that Diddy was hesitant about settling down.

Four years after Sean Diddy Combs and Cassie Ventura broke up, Diddy released a song about how he had to “move on” and stop mourning the loss.

At the 2022 BET Awards, Diddy thanked Ventura “for holding me down in the dark times” when accepting the Lifetime Achievement Award.

After ending things with Puff Daddy, Ventura married Alex Fine in 2019, and the two now have two children together.

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