The Billion-Dollar Love Life: A Complete Timeline Of Rihanna's Dating History, From Chris Brown To A$AP Rocky
Rihanna's love life has been one of the most scrutinized and fascinating narratives in modern pop culture, evolving from tumultuous high-profile romances to a deeply private and celebrated partnership. As of December 2025, the global superstar, fashion mogul, and Fenty Beauty founder is in a stable, committed relationship with rapper A$AP Rocky, with whom she shares two young sons. This current chapter marks a significant, happy evolution in a dating history that has spanned over a decade of public scrutiny, intense media coverage, and profound personal growth.
The journey from her early days in Barbados to becoming a billionaire businesswoman saw the 'Umbrella' singer navigate relationships with some of the biggest names in sports, music, and business. Her relationships have consistently captured headlines, demonstrating her powerful influence both on and off the stage. This is the complete, updated timeline of the men who have been part of Robyn Rihanna Fenty's life.
Robyn Rihanna Fenty: A Brief Biography and Profile
Robyn Rihanna Fenty was born on February 20, 1988, in the parish of St. Michael, Barbados. She is a Barbadian singer, actress, fashion designer, and businesswoman who rose to global fame with her debut album in 2005.
- Full Name: Robyn Rihanna Fenty
- Born: February 20, 1988
- Birthplace: St. Michael Parish, Barbados
- Occupation: Singer, Entrepreneur, Actress, Fashion Designer
- Key Ventures: Fenty Beauty, Savage X Fenty
- Current Status (December 2025): In a relationship with A$AP Rocky, mother of two sons (RZA Athelston and Riot Rose Mayers)
The High-Profile and Tumultuous Romances (2007–2016)
Rihanna's early career was defined by her explosive music and equally explosive relationships. These years saw her navigate intense public scrutiny, particularly concerning two of her most significant and complicated romances.
1. Chris Brown (2007–2009; Rekindled 2012–2013)
The relationship between Rihanna and singer Chris Brown began in the late 2000s and was one of the most talked-about couplings in music. They met as teenagers early in their careers and quickly became a high-profile pair.
The relationship came to a tragic and public end in February 2009 when Brown physically assaulted Rihanna before the Grammy Awards. The incident led to Brown's arrest and conviction, and the images of Rihanna's injuries shocked the world, sparking a global conversation about domestic violence.
In a surprising turn, the two rekindled their romance briefly between 2012 and 2013, citing an unbreakable bond. However, this second attempt was short-lived, and they definitively ended their romantic involvement shortly thereafter, moving on to focus on their respective careers.
2. Drake (On-Again, Off-Again Romance: 2009–2016)
The dynamic between Rihanna and Canadian rapper Drake was a long, complicated, and highly publicized "will they/won't they" saga that spanned nearly a decade. They first met in 2005 when Drake was an extra in her "Pon de Replay" music video.
Their on-again, off-again status was often fueled by collaborations like "What's My Name?" and "Work," and public displays of affection. Drake famously declared his love for her at the 2016 MTV Video Music Awards, stating he had been in love with her since he was 22. Despite the intense connection and public longing, their relationship never fully stabilized, remaining a high-profile romance that ultimately ended due to timing and differing priorities.
Other Notable Connections and Rumors (2010–2016)
During her breaks from her primary relationships, Rihanna was linked to several other high-profile figures, adding layers to her dating narrative:
- Matt Kemp (2010): The Barbadian singer dated the professional baseball player for about a year following her initial split from Chris Brown.
- Travis Scott (2015): She was linked to the rapper, with their relationship being described by some as a brief romance that Rihanna was reportedly unhappy went public.
- Karim Benzema & Lewis Hamilton (2015): Rumors circulated about connections with French soccer star Karim Benzema and Formula 1 driver Lewis Hamilton, though these were never officially confirmed as serious relationships.
- Leonardo DiCaprio (2016): There were persistent rumors of a fling with the Oscar-winning actor, though both parties remained tight-lipped and the connection was never confirmed.
The Era of Privacy and Stability (2017–Present)
Following the highly public nature of her earlier romances, Rihanna entered a new phase, prioritizing stability and privacy. This period led to her longest and most serious relationship before her current one.
3. Hassan Jameel (2017–2020)
From 2017 to early 2020, Rihanna was in a serious, long-term relationship with Saudi businessman Hassan Jameel. Jameel, a deputy president and vice chairman of the family-owned conglomerate Abdul Latif Jameel, offered a stark contrast to her previous musician boyfriends. Their relationship was notably private, rarely featuring in the press and only occasionally captured by paparazzi during their global travels.
This three-year romance demonstrated Rihanna's desire for a stable, low-key partnership away from the spotlight. The couple eventually split in early 2020, reportedly due to different life paths, but the time marked a clear shift toward maturity in her dating life.
The Power Couple: Rihanna and A$AP Rocky (2020–Present)
The most significant and current chapter in Rihanna’s love story is her enduring relationship with rapper A$AP Rocky (Rakim Mayers).
The two were longtime friends and collaborators, working together on music and fashion projects for years. Their romance began quietly in 2020, with sources confirming they went official that summer after years of friendship.
Unlike her previous relationships, the connection with Rocky has been celebrated for its genuine foundation in friendship and mutual respect. They made their relationship public in a stunning pregnancy reveal in January 2022, showcasing a new level of openness and joy in her personal life.
The Family Life and Future
As of December 2025, Rihanna and A$AP Rocky are one of the world's most recognizable and beloved power couples, deeply focused on their family. They have welcomed two sons: RZA Athelston Mayers (born May 2022) and Riot Rose Mayers (born August 2023).
Rocky has frequently expressed his devotion, referring to Rihanna as "The One" and the love of his life. Their partnership is built on shared professional interests, a deep sense of style, and a commitment to raising their family, often seen together at fashion events and on quiet date nights.
The evolution of Rihanna's dating history—from the intense volatility of her youth to the mature, creative, and family-centered partnership with A$AP Rocky—reflects her own transformation from a pop star to a global entrepreneur and mother. Her current relationship is a testament to finding a bond that is both high-profile and deeply personal, marking a happy, stable conclusion to her long journey in the public eye.
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