Diddy Relationship Timeline: Dating History, Girlfriends & Key Dates

Sean “Diddy” Combs’ romantic life spans three decades. His partners include Jennifer Lopez and Cassie. The “Diddy Relationship Timeline” now sits alongside a 2025 trial and conviction on two Mann Act counts.

Fans still ask how his relationships intersect with his public life. Court records and major outlets detail the chronology. Below is a concise, verified rundown, from the early 1990s to 2025.

Key Milestones in the Diddy Relationship Timeline

Misa Hylton (early 1990s): Diddy dated stylist and fashion creative Misa Hylton at the start of his music career. They share a son, Justin, born Dec. 30, 1993. Their relationship ended years ago, but they remained publicly cordial while co-parenting.

Kim Porter (1990s–2007): Diddy and the model-actor were on and off for years. They share son Christian and twins D’Lila Star and Jessie James. Diddy helped raise Quincy, Porter’s son from a prior relationship. They split for good in July 2007. Porter died in 2018. Diddy has repeatedly honored her publicly.

Jennifer Lopez (1999–2001): The pair dated for two years and attended the 2000 Grammys together. Lopez later cited infidelity in a 2003 interview as a reason for their split. The two have been friendly in later public moments.

Sarah Chapman (mid-2000s): Diddy and Chapman were friends and share a daughter, Chance, born while he was still involved with Porter. Their relationship was not framed as a traditional romance in reporting, but they co-parent.

Cassie (2007–2018): Diddy and Casandra “Cassie” Ventura were on and off for nearly a decade. In Nov. 2023, Cassie filed a lawsuit alleging rape and abuse; it settled the next day. In May 2024, hotel security video from 2016 surfaced, and Diddy later apologized and confirmed it showed him. Cassie testified at his 2025 federal trial. A jury in July acquitted him of sex trafficking and racketeering but convicted him on two prostitution-related counts.

Yung Miami (2021–2023, situationship): Diddy and the City Girls rapper were linked in 2021. In June 2022, he said “We date” on her podcast. She later described them as “single, but dating.” They attended the 2023 Met Gala together and said they did not put titles on it.

Yung Miami and Sean ‘Diddy‘ Combs

Dana Tran (2022–present, co-parenting): Diddy announced the birth of daughter Love Sean Combs in Oct. 2022. Public records and reporting identified Dana Tran as the mother. Love’s birth added a seventh child to the family.

2024–2025 legal backdrop: Diddy was arrested in Sept. 2024. His New York trial began May 12, 2025. On July 2, 2025, the jury returned a split verdict. He now faces sentencing under the Mann Act. His children asked the judge for leniency in October 2025.

How the relationships intersect with recent court developments

The Mann Act convictions relate to transporting people across state lines for illegal sexual activity. Prosecutors argued Diddy arranged “freak off” encounters that were recorded. Defense lawyers sought a much shorter term and emphasized alleged consent and his philanthropy. The judge said he would weigh violent conduct described in testimony even after acquittals on broader counts.

Cassie’s role is central to the modern timeline. Her 2023 lawsuit preceded the federal probe. The 2016 hotel video, released in 2024, led to Diddy’s public apology. Cassie later testified in May 2025. These events reframed public discussion of his past relationships.

Where the Diddy Relationship Timeline stands now

Diddy’s family remains a public focus. His daughters spoke at sentencing and asked for mercy. The court will determine the length of his imprisonment. The personal timeline therefore splits: past partners, current co-parenting, and a legal chapter still unfolding.

Bottom line: The “Diddy Relationship Timeline” covers Misa Hylton, Kim Porter, Jennifer Lopez, Sarah Chapman, Cassie, Yung Miami, and co-parent Dana Tran. The 2025 verdict and sentencing hearings now frame how these stories are discussed. Expect further updates after the final sentence is imposed.

FYI (keeping you in the loop)-

Q1: Who are Diddy’s most public long-term partners?

Kim Porter and Cassie defined long stretches of his personal life. Jennifer Lopez was a high-profile two-year relationship from 1999 to 2001.

Q2: How many children does Diddy have and with whom?

He has seven children with four women: Misa Hylton, Kim Porter, Sarah Chapman, and Dana Tran. Love Sean Combs was born in October 2022.

Q3: Did Diddy and Yung Miami ever make it “official”?

He confirmed “We date” in June 2022, while she described them as “single, but dating.” They did not put titles on it.

Q4: What was the outcome of Diddy’s 2025 trial?

He was acquitted of racketeering and sex trafficking. He was convicted on two counts related to transportation for prostitution under the Mann Act.

Q5: Why is Cassie central to recent coverage?

Her 2023 lawsuit, the 2016 hotel video released in 2024, and her 2025 testimony placed their past relationship at the center of the case narrative.