Did Trina and Trick Daddy Ever Date?

For over two decades, Trina and Trick Daddy have represented Miami hip-hop and shown that rappers from the 305 aren’t to be taken lightly. Their friendship dates back further than their time in the music industry, and their complicated relationship over the years — some of which is chronicled on Love & Hip Hop: Miami — has led some to question how deep their relationship actually is.

Rapper Trina performs onstage during 10th Annual ONE Musicfest at Centennial Olympic Park on September 7, 2019 in Atlanta, Georgia | Paras Griffin/Getty Images Trina dated Trick Daddy’s brother

Trick Daddy and Trina’s relationship dates back to their years at Miami Northwestern High School. Trina was a majorette and was voted “Best Dressed” during her senior year, while Trick ended up in prison on a cocaine trafficking charge after graduating. They both had different paths, but they shared a love for Derek Harris, also known as Hollywood, Trick’s half-brother and Trina’s longtime boyfriend.

However, Hollywood was murdered in 1994 while Trina was still in high school. “It was a very disturbing moment,” she recalled in an interview with VladTV. “I never really understood it. I was really young and I just didn’t understand how somebody could be so great of a person and someone could do that.”

(l-r) Trick Daddy and Trina perform on April 9, 2001 | Paul Drinkwater/NBC/NBCU Photo Bank Trick Daddy convinced Trina to become a rapper

In the late ’90s, Trina was working as a beautician in Miami and had no dreams of becoming a musician. Trick Daddy had already released an album and invited Trina to appear on his single “Nann” in 1998.

“I never really thought of doing music like that; I just did it for fun,” she told the Broward-Palm Beach New Times. “At that time, I was studying to get my real estate license. I wasn’t interested in doing music; I just wanted to make real money.”

(L-R) Trina and Trick Daddy at Revolution on February 4, 2016 in Fort Lauderdale, Florida | Thaddaeus McAdams/WireImage

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Inside Trina and Trick Daddy’s relationship

Over the years, Trina and Trick Daddy have had several public disagreements as well as reunions and displays of love. Musically, Trick’s biggest criticism of Trina for nearly two decades has been her ability to cross over into other genres such as R&B as opposed to sticking to the hardcore hip-hop sound of “Nann.”

“I don’t know if Trick knows what it means to evolve or not, but I do,” she told the Miami New Times in 2005. “He’s street and that’s all he’s going to ever be. I came out being street, I came out being sexy, and now I’ve moved on to still being street but also being more mature and more classy… You have to grow to be a superstar and not just a rap artist.” A similar argument led to the demise of their joint TNT project, which was shown on Love & Hip Hop: Miami.

In their first few years on the scene at the turn of the century, rumors flew that the two were an item romantically. They never confirmed a relationship, but they’ve both poked fun at the idea: according to Bossip, Trick has alluded to a fling with Trina, while Trina herself named Trick among other male rappers on her 2004 single “I’m Leaving You (Big Ol’ D*ck),” where she talks about bedding her peers. Since then, Trina has had semi-public relationships with rappers including Lil Wayne and French Montana.