Diddy and his ex Misa Hylton's relationship explored

Amid the backlash that Diddy is getting at the moment following leaked footage of him assaulting his then-girlfriend Cassie Ventura and his subsequent “apology” video, many are curious about the rapper’s previous relationships - one being his first public relationship with Misa Hylton.

Combs and Hylton, who started dating in the early 1990s with both early in their chosen careers, welcomed a son before they called it quits soon after. Hylton is a fashion designer and stylist, best known for styling many hip-hop and R&B artists like Mary J. Blige and Lil’ Kim.

The ex-couple reportedly remained fairly friendly following their split, although Hylton had called out the rapper a handful of times over the years.

---

All we know about Diddy and Misa Hylton's relationship

Combs and Hylton began dating in the early 1990s as they were starting their respective careers. Misa Hylton was a budding stylist at the time, while the rapper started as an intern at Uptown Records.

In a 2018 conversation with The Premium Pete Show, Hylton shared a glimpse of her and the rapper’s relationship decades ago. Recalling their humble beginnings before Combs was promoted to A&R at Uptown Records, she mentioned the rapper “sneaking on the train to get home,” adding that “he used to scrape up for pizza.”

Hylton had initially worked as the rapper’s assistant before the latter gave her her first big break, styling Jodeci for his Gotta Love music video. Her career took off soon after.

Sean Combs and kids (Image via Jason Kempin/Getty Images)

The two welcomed their son, Justin Dior Combs, in December 1993. However, the couple called it quits shortly after their baby’s birth because Diddy allegedly “wasn’t ready to settle down and get married” as his career was starting to take off.

Hylton got candid about the cause for the split in The Premium Pete Show, saying:

"Youth. You know, we were very young. Our lives changed just like that really quickly, and you know, he wanted to experience life in a different way."

---

Diddy and Misa Hylton's various interactions following their split

While the couple decided to end their romantic relationship, they continued to be friends and co-parents to their son.

2010: The now ex-couple reunited for their son’s 16th birthday

They had a family reunion for their son’s star-studded 16th birthday bash in New York in 2010. The “Prince of New York”-themed party was attended by Nicki Minaj, Trey Songz, Lil’ Kim, and Teyana Taylor, among others.

---

2019: Hylton attended Diddy’s 50th birthday celebration

Sean Combs (Image via Allison Shelley/Getty Images)

Misa Hylton was among the famous names to grace Diddy’s 50th birthday celebration in Los Angeles in December 2019. The star-studded event was attended by a slew of A-listers in the music industry, including Beyonce and Jay Z, Post Malone, Kanye West and Kim Kardashian, Offset, Cardi B., and more.

---

June 2023: Misa Hylton slammed Diddy after their son’s DUI arrest

The now mom of three slammed Diddy in cryptic posts via her Instagram Story after their son, Justin, was arrested for a DUI and later charged with a misdemeanor.

She referenced Diddy’s partnership with alcohol company Diageo. Hylton mentioned in the post:

“How [do] you go from one of the greatest to ever do it to making all your money off alcohol and suing the damn alcohol company.”

She further wrote:

"Sell something healthy that builds people up. I’m sick of it!!!!! NOT MINES.”

---

March 2024: Hylton defended her son after he was handcuffed during Diddy’s home raid

After the infamous raid in Combs’ home in Los Angeles, where Justin and his brother Christian were present, Hylton spoke about the “overzealous and overtly militarized force” used by law enforcement during the raid. She shared footage of the incident where her sons were held at gunpoint and handcuffed.

Hylton also wrote in the caption:

“If these were the sons of a non-Black celebrity, they would not have been handled with the same aggression.”

---

Misa Hylton recently voiced her support for Cassie Ventura

As the rapper’s trouble continues, this time from leaked 2016 assault footage of then-girlfriend Cassie Ventura and his subsequent apology video, Hylton voiced her support for Ventura in an Instagram post. She wrote about being “heartbroken” for Cassie and the “horror of her abuse.”

Sharing images of seven of Combs’s children, Hylton also wrote in the caption:

“These young people were raised by women who want the best for them - we put God and education first and have always been united in our mutual effort to support their dreams. Two of the youngest do not have their mother here and it has been our duty to support them.”