Floyd Mayweather Jr. isn’t just known for his undefeated boxing record — the champ has also made headlines together with his high-profile love life. From models to R&B singers, Floyd’s dating history is as glamorous and complex as his profession. We’ve rounded up his most famous girlfriends, past relationships, and rumored flings, so you possibly can see who has captured the eye of the Money Team legend:

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Josie Harris: Family First, Through The Ups And Downs

Floyd and Josie Harris shared a long, complicated history spanning roughly 15 years and producing three children — two sons and a daughter. Their relationship seemingly had its justifiable share of drama; in 2011, Floyd served 90 days in Clark County jail after pleading guilty to a reduced domestic violence charge and no-contest to 2 harassment charges stemming from a 2010 incident. Tragically, Josie passed away in 2020, however the bond they shared and the family they built seemingly remain an undeniable a part of Floyd’s personal story.

Melissia Brim: Keeping It Real As Floyd’s Co-Parent

Melissia Brim is one other vital figure in Floyd Mayweather Jr.’s love life. She is the mother of his daughter, Iyanna “Yaya” Mayweather, born in 2000. Floyd and Melissia dated within the late Nineteen Nineties, with their relationship ending around 2000, but despite their split, they’ve managed to keep up a co-parenting relationship through the years. While Melissia mostly stays out of the general public eye, her connection to Floyd and their shared daughter keeps her as a key a part of his family story.

Jennifer Duran: Floyd’s Mystery Romance From Back In The Day

Jennifer Duran was one in all the ladies linked to Floyd, first gaining attention throughout the early years of his fame. Floyd introduced Jenn to the world back in 2018, sharing glimpses of their relationship on social media. That very same yr, Jenn announced she was pregnant with what was reportedly Floyd’s fifth child. But unfortunately, she suffered a miscarriage, and the 2 apparently went their separate ways.

#1

Shantel Jackson: The One Who Almost Got Away

Shantel Jackson, a model and socialite, dated Floyd Mayweather from 2006 to 2013, even getting engaged in 2011 before their tumultuous split. Their breakup made headlines, involving accusations of assault, harassment, and a 2014 lawsuit filed by Jackson, keeping fans glued to each development. Despite the drama of the past, they appeared to have smoothed things over in recent times, with Jackson even sharing a birthday tribute to Floyd in 2026, reminding everyone that some exes never fully disappear from the highlight.

#2

Keyshia Cole: Did They Or Didn’t They?

Singer Keyshia Cole was linked to Floyd Mayweather for a time, sparking a flurry of online speculation and fan buzz. In 2017, photos of the 2 together fueled rumors they were dating, but Cole explicitly denied any romantic involvement, insisting they were just friends. Still, fans weren’t entirely convinced, and lots of continued to invest a few possible fling, proving that in Floyd’s world, even denied romances can’t escape the highlight.

#3

Was Chilli A Close Friend Or Almost Flame?

Chilli of TLC and Floyd Mayweather maintained a detailed, largely platonic friendship for years, even appearing together on her VH1 reality show ‘What Chilli Wants’ around 2009–2010. Although there was visible chemistry and the 2 reportedly dated briefly, Chilli described Floyd as a friend that she didn’t have a romantic relationship with. Fans couldn’t help but speculate about their connection, fascinated by the combination of R&B star power and boxing royalty, and the friendship kept many wondering what might have been.