9 most intriguing moments from Trina’s “Caresha Please” interview

Yung Miami dropped her latest episode of “Caresha Please” with her guest being none other than Trina. Viewers ate up her previously aired interview with G Herbo a few weeks back, and the City Girls turned famed host shared a deep and enthralling conversation with the rap vet in the latest installment of her show.

Over signature Caresha Please cocktails, the two Miami rappers discussed dealing with trauma, love in the industry, and of course, they enjoyed a mini segment with Yung Miami’s new card game Resha Roulette.

Check out the nine best moments from the new episode of “Caresha Please” starring the baddest below. Plus, tune in here if you missed it.

1. On being recognized with BET’s I Am Hip Hop award

Starting of the episode, Yung Miami acknowledged the 305 legend and her trailblazing career. That included receiving the I Am Hip Hop Award in 2022. Trina expressed, “It was a good feeling, I felt like it was about time, I felt like I deserved it.”

With over 20 years of groundwork, the emcee, entrepreneur, and TV producer was finally the recipient of an award that recognized her contribution to the music industry as a rapper. Yung Miami showed gratitude for Trina being able to receive her well-deserved flowers while she was still here to smell them. Trina also admitted that being confident is what kept her elevated throughout her journey. “It was just natural to just remain confident and really remain true to who I am,” she added.

2. On considering surgery

Today, it’s a popular activity in entertainment to get surgery to enhance body features and overall appearance. At the peak of Trina’s music career, women were more natural and didn’t participate in surgery as often. Although she considered getting a boob job, she never went through with it. “I did want to go a cup size up, I was almost obsessed about it,” the Miami legend admitted. However, when the facts came out about having to get them redone every 10 years added to fears of implant ruptures, she ultimately decided it was not a process that was going to work for her.

3. On new artists paying homage to veteran rappers who paved the way

Yung Miami inquired about how the 305 icon felt about new girls in the rap game showing love to those who came up before them to which Trina responded, “I feel like you should. It’s just a respectful thing because there’s going to be another girl that comes up after you.” She added, “That’s like saying we don’t pay homage to Janet Jackson or Whitney Houston or the greats that came before us. You do! Because they are who paved the way.”

When Trina came into the game, there weren’t many women rappers. Yung Miami was interested in hearing what the emcee thought of the growth in feminine presence in the rap game to which Trina exclaimed her satisfaction. Even though there are similarities, the new artists have different struggles, come-up stories, and backgrounds that offer different levels of style and overall artistry in the music we hear now.

4. On finding discomfort with being called a “Role Model”

It’s common to admire The Baddest B**ch for her longevity, authenticity, and growth. However, the hip hop legend is not fond of being considered someone’s role model. “I will make a mistake. I may do something you don’t like. I feel better when people go, ‘You have inspired me in some way,’” Trina said. Understandably, the presumptions that come with being someone’s role model may include expectations that the songstress would not want to be responsible for if there were ever any disappointments.

5. On working with Trick Daddy

If you are a real hip hop fan, it’s impossible for you to have heard about Trina without hearing about the Dade County OG Trick Daddy. Trick and Trina make an undeniable duo. There are over 20 years of business and friendship between the duo. So, it was only right to ask the one person who was able to share that experience firsthand, for decades, what it was like working with Trick. After recording their 1998 bop, “Nann Ni**a” that was really the one time she worked side by side with him inside the studio, Trina explained. Afterward, she would invite the legendary rapper to the studio toward the end of her session. “I didn’t want to be in there at the same time with him. He is very opinionated and brutally honest. It would be triggering, so sometimes I had to do my own thing,” explained the Diamond Princess. “You’ve just got to know Trick, love him for who he is.”

The Dade County pair also pursued a morning radio talk show, “Trick and Trina.” Yung Miami and Trina giggle at the fond memory of the City Girls rapper calling into their show as one of their listeners as she drove her kids to school. Now that the show has come to an end, Yung Miami needed to know what happened. According to Trina, they signed a two-year deal with the option to stay. However, in their first year, the pandemic plagued the nation and halted all in-person interaction forcing them to conduct interviews with artists over Zoom calls, etc. Also, the managers of the show concluded that the Trick and Trina show went over-budget and ultimately decided to not renew their contract.

7. On relationship status and starting a family

Per the emcee, Trina current relationship status is “just vibing.” In September 2021, it was announced that she was engaged to her then-boyfriend, Raymond Taylor. As she walked “Caresha Please” viewers through the details of her engagement, she admitted that she was still processing what happened before news broke out online the very next day. She was bombarded with congratulatory texts and questions about the wedding before even fully comprehending the monumental moment herself. Although it was not specified what caused their engagement to end, she did highlight how maintaining a relationship while trying to face grief and tragedy will make you pull away, so that you can prioritize your emotions.

When asked about her family dynamics and why she doesn’t have any children, Trina also admitted that suffering three miscarriages discouraged her immensely. “That was a lot for me. It just came to a point where I was like, ‘Well, what’s the problem?’ When my mom got sick, I just went into this phase of I don’t even want to have a kid and my mom is not here. How do I raise a kid without my mom?” The hip hop icon is allowing her body two more years to try and bear a child. But, at this time, she is really just focused on work and making money.

7. On dealing with grief while in a relationship

When speaking about her previous engagement, Trina explained that she was very happy once she compartmentalized her emotions about the whole ordeal until tragedy struck and that phase of happiness did not last long. This impacted her relationship. “I can’t focus on that when I’m in this space [of grief]. I need to get out of this space,” she said. Yung Miami agreed with the difficulty of going through a tragic time while in a relationship. In 2020, the father of Caresha’s son passed away because of a shooting. During this time, she was in a relationship with her then-boyfriend Southside, who is the father of Yung Miami’s daughter. As the ladies relate to one another’s trauma, Trina summarized, “No matter the love and support, there is still a void. It’s a dark space that’s never going to go away.”

8. On dating in the industry

The Diamond Princess was ready for all the smoke in a segment where Yung Miami asked Trina if she’d prefer “This or That.” The baddest cleared up rumors about her and Torey Lanez, and even clarified that she and Missy Elliott never dated, but that Missy taught her a lot about business management.

Miami: “Famous or Non-Famous?”

Trina: “Famous! When I say famous…meaning somebody that is worth your value. You should have someone that’s on your stature.”

Miami: “Lil Wayne or French Montana?”

Trina: “Lil Wayne. Totally two different people, two different artists. I was engaged to Wayne. In a whole relationship. That was a different phase.” She added, “French is a cool person, we had a great friendship, and I learned a lot from him. But, when he tried to do his big one, it wasn’t big enough. Not for me, I’m the wave!”

9. Playing Resha Roulette

Yung Miami dropped a new card game called Resha Roulette not too long ago. Since then, she’s closed out each “Caresha Please” episode by getting her guests to play, which allow us to dive deeper into not only the interviewee, but Ms. Caresha Brownlee herself! In this episode, we learned that Yung Miami is not responsible for the full course Thanksgiving dinner with only three seasonings in her pantry. However, Bobby Lyte screamed from behind production vouching for Trina’s skills in the kitchen. On the other hand, we learned that Trina is not into BDSM. A Resha Roulette card that Trina pulled said: “Take a shot if you are into Fifty Shades of Gray type of sex.” Trina confidently answered, “I’m not into that. Like tied up and all that? You mess around and not untie me, I don’t have time for that.” Plus, Yung Miami revealed how she’s in to golden showers — Most definitely closing the segment with laughter and a new love for both ladies representing hard for Dade County, Miami.