Lil Scrappy & Diamond Relationship Timeline

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LOS ANGELES, CALIFORNIA - JUNE 25: Lil Scrappy and Diamond attend the BET Awards 2023 at Microsoft Theater on June 25, 2023 in Los Angeles, California. (Photo by Johnny Nunez/Getty Images for BET)

All the highs, lows, and everything in between.

In the ever-changing world of Hip Hop, where beats and rhymes intertwine with personal lives, the relationships of its prominent figures become as intriguing as the verses they spit. Lil Scrappy and Diamond, for example, are both prominent figures in the industry. As such, their relationship garnered significant attention as it developed over the years. As their romance unfolded amid the spotlight of fame, the couple took fans on a rollercoaster ride through their highs and lows. Although they were last spotted in 2023, Diamond’s recent engagement to someone else has left their shippers quite confused. Let's delve into the journey of the two artists-turned-reality-tv stars.

Read More: Lil Scrappy & Erica Dixon's Relationship Timeline

Early 2000s: Small Beginnings

In the early 2000s, Lil Scrappy, born Darryl Kevin Richardson III, and Brittany Nicole Carpentero, a.k.a Diamond, initially encountered each other while navigating the early stages of their rap careers. During this period, Lil Scrappy had recently garnered acclaim for his singles "No Problem" and "Money In The Bank.” Diamond, on the other hand, was establishing her presence as a notable member of the popular rap group, Crime Mob. Their paths converged at a pivotal moment in their musical journeys, setting the stage for a connection that would soon captivate the Hip Hop scene.

2008: Public Appearances 

MIAMI - AUGUST 12: Recording artists Diamond (L) and Lil Scrappy attend the second day of the TJ's DJ's 2nd Annual Tastemakers Music Conference at the Hyatt Regency August 12, 2007 in Miami, Florida. (Photo by Ray Tamarra/Getty Images)

Although the couple is suspected to have been dating since 2005, they made their relationship public in 2008. The duo often made appearances at events together. Moreover, they shared glimpses of their relationship on social media, allowing fans to witness their highs and lows. However, maintaining a relationship in the public eye proved to be challenging, and the couple faced its fair share of ups and downs.

Read More: Diamond's Engagement Leaves Lil Scrappy Fans Confused

2011: Diamond And Lil Scrappy Break Up

MIAMI - AUGUST 13: Recording artists Diamond (L) and Lil Scrappy attend the Second Annual Ozone Awards at the James L. Knight Center August 13, 2007 in Miami, Florida. (Photo by Ray Tamarra/Getty Images)

Six years after they began dating, the couple’s relationship came to an end. Diamond subsequently moved on to date Soulja Boy. Rumors circulated about Lil Scrappy's alleged infidelity, and the public was quick to speculate about the reasons behind their split. Although Diamond claimed that the breakup was due to conflicting schedules, Lil Scrappy alleged that it was because Diamond had cheated on him with Soulja Boy. He also stated how devastated he was over the breakup.

“Ya boy cried. You feel me, I cried,” he said. “I had a puddle right here. I’m talking about shirt wet. You know, let me tell you something, when I cried like that, I knew then I never been in love before.” After the breakup, Lil Scrappy continued on with his artistry.  He appeared on Love & Hip Hop: Atlanta, which provided viewers with a closer look at his personal life. Diamond also ventured into reality TV, participating in shows like Sisterhood of Hip Hop.

2014: Diamond Claims Lil Scrappy Was Abusive

In 2014, Diamond was on The Breakfast Club, and spoke about her relationships with Lil Scrappy and Soulja Boy. She claimed that Scrappy had been abusive during their relationship. “He was mentally abusive… physically abusive,” she said. “Yeah, he got some issues. Some demons, he needs some help. I think we’re better off as friends. I don’t want to try to continue to be in a relationship and we end up not liking each other… hating each other.” Lil Scrappy and Momma Dee subsequently spoke to TMZ to slam the accusations down.

Read More: Lil Scrappy: Exploring His Career From Rap To Reality TV

2023: Rekindled?

Over the years, Lil Scrappy and Diamond had both moved on with their lives. Both artists have been pursuing their individual careers, as well as personal growth. In June 2023, the pair reunited and walked the BET Awards red carpet together. Along with their seemingly rekindled love, came rumors that Diamond was pregnant with Lil Scrappy’s child. Not long after, the rapper denied the rumors in an episode of Love & Hip Hop: Atlanta.

In November 2023, Diamond posted a picture of her and Lil Scrappy in bed. The picture was of the rapper’s back, and the caption implied that the two were together. This notably came just after Lil Scrappy’s ex, Erica Dixon, shared pictures of the two together for Halloween. Overall, this strange love triangle has sparked a cascade of reactions from fans and followers, all eager to piece together the unfolding narrative. However, it’s uncertain what direction their story might take, especially now that Diamond is engaged.

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About The Author
Demilade Phillips has been a Features Writer for HotNewHipHop since 2023. The self-proclaimed music fanatic deals with most things Hip Hop and R&B, while also covering film, television, and the entertainment industry at large. When he’s not working, the International Relations graduate is either binging anime, immersing himself in the underground EDM scene, or crafting up original pieces.