Flavor Flav's Dating History: The Women He's Dated and Moms of His Children

Flavor Flav, whose real name is William Jonathan Drayton Jr., has an extensive dating history with some notable women. The former rapper has eight children from four of the women he has dated, and one of them is his wife.

Flavor Flav is a former rapper who became famous in the late 1980s as part of the hip-hop group Public Enemy, which he co-founded. He is a musical prodigy who can play 15 instruments, including the piano, guitar, and drums.

As his musical career succeeded and he gained a massive following, his fans became interested in his dating life. In addition, due to his reality show, the rapper's dating life was constantly carried by the media.

The Public Enemy rapper has been in over eight known relationships, including a two-year relationship with the model Beverly Johnson. While they were dating, they lived together in New York.

The end of their relationship led Flav to become a reality television star. He starred in the third season of "The Surreal Life," along with other celebrities like Jordan Knight, Dave Coulier, and an actress whom he later dated.

Women He Dated

Flav's first known relationship was around when he became famous. Then, he was dating Karen Ross, and they welcomed three children. Their first child was Shanique, followed by Karren and Karla.

Their relationship ended in 1991 after the rapper confessed to having assaulted her. His guilty plea got him 30 days in jail, and he lost custody of their children.

In the 1990s, Flav started dating Angie Parker, and they also welcomed three children. Their first child was Da'Zyna Drayton, followed by Quanah Drayton and William Drayton.

Their kids appeared on the first season of "Growing Up Hip Hop: New York" with him. The rapper was always in and out of jail. His constant legal issues may have contributed to their breakup.

Besides his legal issues, Flav was also with addiction and had to re-enter rehab in the late 1990s. By 2000, he was dating the model Beverly Johnson, and they lived together with two children from her previous relationship.

Two years later, the rapper was sentenced to nine weeks in jail after he was arrested for multiple parking tickets and driving with a suspended license. After serving his time, he broke up with the model.

While starring in "The Surreal Life" in 2004, he met fellow castmate and actress Brigitte Nielsen. They soon started dating, and their relationship earned them a spinoff series 'Strange Love."

The series lasted for 11 episodes, and so did Flav's relationship. The actress moved on, and in 2006, she married her Italian husband.

In the search to find love, Flav started his reality show, "Flavor of Love." The show featured 20 women who wanted to date the rapper living in a mansion.

The show, with a format like "The Bachelor," ended in March 2006 with Transportation Security Administration agent Nicole "Hoopz" Alexander being the winner. They dated for a while but decided to remain friends after their breakup.

Flav returned with the second season of "Flavor of Love" in August 2006 and hosted another set of twenty women in a mansion. After 12 episodes, the show ended in October 2006.

Chandra Davis, also known as London "Deelishis" Charles, emerged as the winner for the second season. Their relationship also did not last long.

Flav also dated Tiffany "New York" Pollard after she appeared in the first two seasons of his series and was the runner-up in both seasons. Their relationship was on-and-off and also did not last long.

In February 2008, the rapper returned with his show's third and final season. The show ended in May 2008 with Tresha "Thing 2" as the winner and Candace Cabrera "Black" as the runner-up.

However, on the season 3 reunion, the rapper proposed to Elizabeth Trujillo, the woman who welcomed one of his sons in 2007, instead of dating the show's winner.

Flavor Flav had been in an on-and-off relationship with Trujillo before he welcomed his seventh child, Karma. The couple reportedly got married, but there is no information on their wedding date.

In 2019, Flav and his former assistant Kate Gammell had a romantic relationship that produced the rapper's eighth child. That same year, she accused the rapper of not providing child support for their son, Jordan.

The Public Enemy rapper initially denied being the father of the boy. However, she filed a paternity suit that confirmed the rapper as the boy's father.

His Ex Pregnant at 54

In 2018, one of Flav's ex-girlfriends, Nielsen, announced her fifth pregnancy while she was 54. On hearing the announcement, the rapper revealed that he was excited. He said:

"This pregnancy at over 50, it’s amazing! It shows everybody in the world that everything and anything is possible. I was proud. I was siked to see her belly that big."

In his excitement, he said he flipped when he saw the social media post and knew his friend could do it as other older women had gotten pregnant in the past.

Why We Don't Hear from Him Anymore

Flav's musical career has been passive for some years, and some of his court appearances may have played a part. In 2012, the police arrested him for domestic violence against Trujillo and her teenage son, Gibran.

The couple had begun arguing around 3:30 a.m. before it became physical. During the arguments, the rapper also allegedly chased her son with a knife while threatening to kill him.

The police charged Flav with battery and assault with a deadly weapon, even though he denied threatening to kill Gibran. As the case went to court, he pled guilty to misdemeanor domestic violence charges.

He also entered a plea deal to reduce his charges and not spend jail time. The rapper got a year of probation and was to spend 12 domestic violence counseling sessions with Gibran.