Who has Floyd Mayweather Jr dated? Girlfriend List, Dating History

The former American professional boxer, Floyd Joy Mayweather Jr, who currently works as a professional boxing promoter, is one of the most famous male boxers to don the gloves and enter the ring, and requires no formal introduction. In his prolific career as a boxer, Mayweather earned numerous nicknames, which include ‘Pretty Boy’, ‘Money’, and ‘TBE’ (The Best Ever), not only because he is one of the highest earning boxers of all time, but also because he built a reputation as a formidable opponent in the ring. Having competed in five weight divisions of professional boxing over 19 years between 1996 and 2015, Floyd won a total of fifteen major championships, eventually retiring with an undefeated record.

In 2017, Mayweather made a one-fight comeback, though these days mostly steps into the ring to face the challenges of famous YouTubers, such as Paul Logan, and other MMA fighters looking to test their steel against the world’s greatest boxer.

Mayweather also won a Bronze medal at the 1996 Olympic Games, competing that year as an amateur, and built an impressive record that surpassed his closest competitors, which includes the likes of Lenox Lewis, Mike Tyson, Evendar Holyfield, Manny Pacquiao, and Oscar De La Hoy.

Upon retirement in 2017, Mayweather’s record was undefeated as a professional with 50 straights wins, including 26 consecutive world title wins, 10 by knockout, 23 wins in lineal title fights (nine by knockout), and to prove he is the best of the best, Mayweather won 24 fights (seven by knockout) against former or current world title holders, 12 wins (three by KO) over former or current lineal champions, and four wins (one by KO) against International Boxing Hall of Fame inductees. Floyd is still considered the best defensive boxer in the world, as well as the most accurate puncher since the introduction of CompuBox, a computerised system that aids referees with the punch scoring in official matches.

He currently holds the highest plus-minus ratio in modern recorded boxing history. However, what else can be expected of a man from a family of legendary boxers? Born on 24 February 1977 in Grand Rapids, Michigan, as Floyd Joy Sinclair, the son of former boxer Floyd Mayweather Sr, Floyd lived his life never considering any other profession other than boxing. Growing up, Mayweather trained under the influence of his father and his paternal uncles, Jeff and Roger Mayweather, who were both professional boxers in the ‘80s and early ‘90s.

As a child, Floyd would accept his mother’s family name, Sinclair, though later adopted his father’s surname by which he competed professionally. In the ‘80s, while still a pre-teen, Mayweather lived in New Brunswick, New Jersey, residing with his mother’s relatives in the Hiram Square neighborhood.

During this time, Mayweather’s family experienced financial insecurity, often living without access to electricity, and he would share a bedroom with as many as seven people. According to the champion boxer, his poor childhood taught him to appreciate the wealth and fortune he accumulated through his successful sporting career.

Mayweather later moved back to Michigan to live with his father, where Floyd attended Ottawa Hills High School in Grand Rapids, but never matriculated. Mayweather paints a grim picture of his childhood, stating that his father, Mayweather Sr, was more attentive and loving with his older sister, and claimed that his father tended to be negligent, only spending time with him at the gym for his training, and would often whip him as a teenager for misbehaviour.

However, Floyd Sr holds steadfast that he did his best as a father, though admits he had to hustle drugs at night to provide for his children. According to Floyd Sr, Mayweather Jr had enough money, food, and wore the best clothing. He also stated that he dedicated his days training Floyd Jr, and if it wasn’t for him, Mayweather would not have become the legend he is known as today.

On the contrary, Mayweather Jr was forced to drop out of high school in an attempt to provide for his mother and maternal grandmother by competing in amateur boxing. Ultimately, Floyd ended his amatuer career with 86 wins and 8 losses, winning the Golden Gloves championship in 1993, ‘94 and ‘96.

Following his appearance at the 1996 Olympic Games, where he fell in the semi-finals and earned a Bronze medal, Floyd began his professional career.

Within two years of competing, he won his first world title in the super featherweight division, with a win over Genaro Hernandez in the eighth round by technical knockout. After that, Floyd’s career rose to successive new heights, seeing him compete in heavier weight divisions and ultimately making him the boxing champion he is known as today.

Because of his fame, many fans have expressed an interest in the athlete’s life outside of the ring, and not only limited to his love of cars. Just like everyone else, his fans wanted to know who the lucky ladies were who got to see the softer side of this fighter.

Unfortunately, Floyd’s love life is not without controversy, and as one could expect, there were quite a few ladies who became personally involved with the world’s greatest boxer. By all means, they were probably the only ones who could deprive the Champ of his belt.

The Starter Wife

Floyd’s first public relationship was with Josie Harris, the woman who could be considered his high school sweetheart, though most fans of the boxing legend would only know about the relationship because of the controversy surrounding their relationship that came to light during the many years the couple spent together. If not for the many difficulties the two faced, and the many break-downs they survived, Josie and Floyd may even have had one of the most beautiful and inspiring love stories to surface in the sporting world.

The two met long before Mayweather achieved any fame, back in 1995 while Floyd still competed as an amateur boxer. They met at a bowling alley in Las Vegas, Nevada, which also happened to be Josie’s hometown, when Floyd was a nineteen-year-old boxing contender, and Josie was a sixteen-year-old high school student.

The couple started dating shortly afterwards, and for the first couple of years were as in love as only tenagers could be, but things eventually fell apart.

Floyd Mayweather Jr.

Despite spending the greater part of their teenage years and early adulthood together, the two never tied the knot, most likely because of the continuous difficulties Harris and Mayweather’s relationship faced. The couple stayed together for a total of fifteen years, from 1995 until their official split in 2010.

During that time, Josie would give birth to three of Mayweather’s four biological children, namely, from oldest to youngest, Zion, Koraun and Jirah. Unfortunately, as Josie later revealed, she would become the victim of domestic abuse on six occasions, and started seeking the comforts provided by recreational narcotic abuse.

According to Harris, their children would often be witness to Mayweather’s abuse, which ultimately became the motivation behind their decision to end the relationship. However, this was not before rumours surfaced that suggested that Josie had an affair with the professional basketball player and Golden State Warriors all-star, CJ Watson.

These rumours were never confirmed, but according to Josie, this didn’t prevent Mayweather from abusing her. In 2010, shortly before the couple officially called it quits, on 9 September reports surfaced that police were searching for Floyd after Josie pressed charges against her soon-to-be ex-boyfriend. According to reports, Floyd entered Josie’s home and assaulted her in her sleep, dragging her by the hair and repeatedly beat her in front of their children.

A then ten-year-old Koraun fled the house and sought aid from a nearby security guard, who alerted the police. At this point, Floyd fled the scene, but in 2012 the court convicted him for this incident, for which he served 90 days in jail, paid a fine of $2,500, and had to complete 100 hours of community service. Floyd later told the press that he became enraged after learning that Josie once again used narcotics, stating that he was guilty of attempting to intervene with her bad habits.

Sadly, on 10 March 2020, Josie Harris passed away from a mixed drug overdose caused by the intake of Fentanyl and Alprazolam. She was discovered in her car outside her Valencia home in California, and pronounced dead at the scene.

In an interview, Mayweather expressed his condolences and grief regarding Josie’s unfortunate passing, stating that he will always have a high regard for her, calling her his heart, family and rock. She will be dearly missed by her children, as well as being remembered as one of the stars of the reality series ‘Starter Wives: Confidential’.

The Side Chick

During his tumultuous relationship with Josie, Mayweather also became involved with several other women, who includes the mother of his fourth child, Melissa Brim. Although Brim never achieved much fame, becoming a professional business woman, she did earn some sort of a reputation as the on-off girlfriend of the boxing prodigy.

The pair dated between 1998 and 2000, though continued to see each other as co-parents of their daughter, Lyanna, and as it happened, Josie wasn’t the only one to file assault charges against Mayweather. Several reports claim that Melissa also called the police on Floyd, who was accused of assaulting Brim in 2001, though was never convicted on these charges.

Floyd Mayweather Jr.

However, in 2004, Floyd pleaded guilty to assault charges against two of Brim’s friends, after they confronted him in a nightclub. Unfortunately, most of the details regarding Mayweather and Brim’s relationship are unknown to the public, as they attempted to keep their affair secret.

Unfortunately, with the birth of Lyanna, their secret reached nearly every front page of gossip tabloids, but none of the publications could reveal any substantial information about their relationship; nonetheless, it was confirmed, but due to Mayweather’s poor behaviour, they didn’t stick together for very long.

The Public Romance

Mayweather next became involved with the American model and actress, Shantel Jackson, who became Floyd’s most famous girlfriend and later fiance. The pair met in 2006 when Shantel, then 21 years of age, was working as a hostess at a social event in Atlanta.

According to Shantel, they began a romantic relationship that quickly became intimate, and she moved to Las Vegas to live with her new boyfriend, the successful boxer Mayweather.

Soon the tabloids caught wind of their relationship, and it quickly became one of the most publicised romances in the sporting world, with fans and gossipers celebrating the union of the couple.

Of course, the tabloids couldn’t get enough of how much money Mayweather was willing to spend on the young model, which included lavish gifts and expensive getaways, but it seemed that Floyd continued in the bad habit of becoming abusive towards the women in his life. In 2014, following several years of dating and even at one point becoming engaged, Shantel ended the relationship. At the time, she also filed charges against Mayweather, accusing him of physically restraining her and threatening to harm her if she didn’t resume their affair.

Unfortunately, things got incredibly messy, especially after Shantel started dating American singer, Nelly. After seeing the pictures Shantel posted on social media of herself and Nelly, she claimed that Floyd threatened to post naked photos of her on his social media accounts.

However, instead of doing so, Mayweather announced to the world the real reason he no longer had any interest in Shantel. According to the boxer, Shantel became pregnant with twins in December of 2013, but had her pregnancy terminated. Floyd stated that he was furious about her decision, posting a sonogram of their late twins on his social media, adding that he was against abortions.

This resulted in Shantel taking legal action against ‘Money Mayweather’, accusing him of assault, battery, defamation, and invasion of privacy. However, Shantel later dropped the charges, saying that she hoped to move on with her life. According to legal documents though, her case against Floyd fell apart, as the court would have likely ruled against her.

Regardless of how it ended, after several good years, Jackson and Mayweather ended their romance without any chance of ever reconciling, as they had done several times before.

The Good Friend

For a long time, a popular fan theory suggested that Floyd may have been romantically involved with American singer, songwriter and television personality, Rozonda ‘Chilli’ Thomas, who had achieved fame as the star and focus of the reality series ‘What Chilli Wants’, and was also as a recognized member of the R&B girls band ‘TLC’.

While fans considered the possibility of a romance between Rozonda and Mayweather, often fueled by speculations circulating the media, as well as Floyd’s appearance on ‘What Chilli Wants’, during a candid interview with Bossip.com, the reality star revealed that they were only friends.

As Rozonda stated, both she and Mayweather have absolute respect for each other, and as such never formed either an intimate nor a romantic relationship. The two have been friends since first meeting in 2008, and continued to maintain a friendship over the many years that passed.

The Life Of A Bachelor

Following his first couple of serious, long-term relationships, it seems as if Mayweather decided that it would be better to enjoy the free lifestyle of a bachelor. Around the same time that Floyd began his friendship with Rozonda in 2008, he also became involved with the American singer and songwriter, Keyshia Cole.

According to most reports, Mayweather and Keyshia have maintained a connection for more than ten years, although with their last known meeting taking place in 2018, following Floyd’s victory over MMA fighter Connor McGregor and YouTuber Logan Paul. The singer shared congratulatory messages to Floyd on her social media, but still no one can tell for certain if the two have ever been romantically involved.

At the time of their meeting, Keyshia was still married to basketball all-star, Daniel Gibson, which made it somewhat unlikely. Both Cole and Floyd have kept their relationship private, and as such few details exist that could confirm an intimate relationship, though it’s clear that the two are certainly friends.

In the years that followed, Mayweather has been linked to several women, though details regarding his hook-ups, dalliances, and romantic conquests remain shrouded in mystery.

In 2011, rumours surfaced that suggested Mayweather may have had an encounter with American model and Playmate Jessica Burciaga. Jessica once was a close friend of Mayweather’s ex-fiance, Shantel, and according to rumour, played a part in the decimation of their engagement. However, these rumours were never confirmed, and seem to be nothing more than wild speculation.

More rumours surfaced around the same time that suggested Mayweather dated the rapper Lil Kim, even going so far as to suggest that the couple were involved for nearly a year. Most of the rumours were based on social media posts, and one occasion when Lil Kim attended Floyd’s birthday bash. It also gained further support because of the active effort on Mayweather’s behalf to bond with Kim’s daughter. However, according to more accurate reports, it seems the two were only friends.

In 2012, Mayweather became involved with the model and fashion designer, Princess Love, with whom it is suggested that Floyd had a two-year relationship. However, it seems their romance was little more than a short dalliance, cut short by Mayweather’s constant obsession with Shantel, and Love’s supposedly secret affair with the rapper Ray-J. Love’s affair eventually became a public romance, and it was clear that things between her and Floyd were over, and by all means seemed irreconcilable.

In 2013, rumours surfaced that suggested that Mayweather hooked up with former child star Lindsay Lohan, after the two were spotted cuddling and dancing at a Halloween party in Connecticut. However, the rumours didn’t last long, and Lohan never confirmed the encounter in her confessional list of romantic conquests, though it can’t be completely ruled out. Considering that the boxer was engaged to Jackson at the time, it seems obvious that Lohan and Floyd would want to keep their dalliance a secret, if anything happened at all!

In 2013, rumours abounded regarding romance between Floyd and the Atlanta actress Erica Dixon. According to reports, Mayweather flew to Atlanta on several occasions in an attempt to spark chemistry between the two, but nothing substantial came from their brief encounters, and any relationship ended as quickly as the rumours died down.

In 2014, pictures depicting a possible romance between Floyd and Instagram sensation Lauren Wood as they enjoyed a luxurious getaway on a private yacht went viral, reaching the internet, making fans of both stars hopeful for something substantial.

Unfortunately, their relationship went down in the history books as little more than a brief encounter – does that sound familiar!?

The Last Known Mayweather Ladies

In 2014, Mayweather became involved with Doralie Medina, a former massage therapist who became known as the girlfriend of the King of the Ring. According to certain reports, the couple dated for more than a year, though sources remain uncertain about the details of their relationship. As it appears, the former boxer turned promoter learned his lesson about dating in the public eye, and made an concerted effort to keep his romance low key.

However, that same year, it was also reported that Mayweather had an encounter with Instagram beauty Ayisha Diaz, with some sources suggesting that the two maintained a friendship for three years running, eventually growing apart and ending their romance in 2017.

Mayweather and Diaz’s relationship was never confirmed, and some publications still dispute whether or not it really happened, especially as in 2015, rumours surfaced about an encounter between Mayweather and Instagram model Aileen Giselle. According to most reports, the two enjoyed a romantic dinner, though nothing substantial followed that hook-up.

In 2016, Mayweather reportedly became involved with a 19-year-old shop attendant, who was later identified as Brit Raemarni. The young woman is an aspiring pop singer, though aside from her fling with the boxing legend, as of yet, hasn’t achieved any prominent recognition in Hollywood. Not even these rumours were confirmed, and as it appeared, Mayweather and Brit only spent a short time together.

Rumours once again sparked wildly in 2016, after Mayweather and Nikki Mudarris, heiress to the Mudarris real estate empire and fortune, shared sweet messages on social media. However, their relationship ended as quickly as the rumours died down, and since then little has been mentioned about any relationship between the two.

In 2017, more rumours suggested that Mayweather had hooked-up with British reality television star, Abigail Clarke. Although the details are fuzzy at best, their encounter is commonly accepted as true, though it’s suggested that it was nothing more than a brief encounter.

The last known woman with whom Mayweather had an actual relationship was the Instagram sensation, Yaya. Note though, that she shouldn’t be mistaken for Mayweather’s daughter Iyanna, who goes by the same ‘Yaya’ nickname on social media. While details are obscure, it’s suggested that Yaya and Mayweather dated for nearly two years, initially meeting in 2016, and eventually separating in 2018.

The latest 2021 reports about Mayweather’s love life suggest that he has been dating former exotic dancer, Anna Monroe. According to these reports, Mayweather even intended to have a child with Anna, and some rumours also suggested that the couple may have become engaged.

The couple met in 2020 at his Las Vegas club ‘The Girl Collection’, and seem to be going strong. Anna has shared several pictures of the couple on social media as they enjoyed vacations at exotic retreats, but Floyd has remained quiet about the relationship, and the reports seem confusing, as another rumour suggests that Floyd is now engaged to another woman, identified as his on-off girlfriend Gallienne Nabila.

Whatever may be the case in Mayweather’s current love life, it seems clear that the undefeated boxing champion is likely keep enjoying the life of a bachelor, certainly without any intention of restricting his romantic exploits in the foreseeable future.

Olivia Wilson

Olivia Wilson is currently a reporter for AffairPost based in London, United Kingdom. Prior to joining AffairPost in September 2018, she was a entertainment reporter. Olivia studied journalism at Cardiff University, graduating in 2010.

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