When Jada Kissed Tupac

Being fashionably late to sophomore-year orientation for the theater department is my intention, a way to make an entrance. We are required to report to the massive performing hall at Baltimore School for the Arts. An imposing room, it’s memorable for its super-high ceilings and a stage built from beautiful dark wood.

As I saunter in, I immediately catch eyes with a new dude across the room who is engaged in an energetic conversation. He’s wearing a thick, old-school alpaca sweater and jeans. He has beautiful brown skin with big brown eyes, heavy eyebrows, and a tiny peanut head.

The minute I turn and notice him, he’s already staring at me. Me catching his eyes gives him the gumption to walk across the room right to me. He smiles a big ole smile, showing off his big ole teeth, and puts out his hand to shake mine.

“Hi,” he says, “I’m Tupac.”

I am struck by the power of that unusual name. Tupac.

From the gate, Pac was an undeniable charismatic who could captivate any room, peanut head or not. He hadn’t yet told me his story or that he was already making moves as a 15-year-old rapper to be the next Rakim or that he had serious acting chops. But I would soon find out all of that and so much more. What I didn’t expect, even with the uniqueness of his vibe, was that this young man and I would create a bond that would impact my life forever.

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“Aight, Pac… kiss me, then.”

Pac and I are standing on my tiny back porch on Price Ave., and the two of us are bantering—about how, maybe if we actually tried to be more than friends, could it work or not?—and I decide to dare him.

During our teen years, it wasn’t really Pac’s good looks that grabbed you, because his sculpted features and unforgettable handsomeness hadn’t quite come in yet. What he did have, even in 10th grade, was pure, unadulterated charisma. We became inseparable from the moment we met. We were kindred spirits in so many ways, and although Pac may have had an attraction to me in the beginning, the more time we spent together, the more we could both see that there was no romantic chemistry between us . . . at all.

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There were no airs between us, either. We could be raw and authentic without the constraints of having to impress each other. There were no butterflies, no tingles in the body, no hot desire to be in each other’s embrace. Rather, there was something far more important unfolding between us—a friendship of a powerful strength, giving us the ability to hold space for each other through some of the most unbearable moments of our lives.

Being as young as we were and as tight as we were, we both found it confusing at times that we weren’t drawn to each other romantically. Hence the day he got on my last nerve about the possibility of being more than friends, and I dared him to kiss me.

Without hesitation, Pac grabbed me in his arms and did just that. The kiss lasted a few seconds before we both pulled away in mutual disgust. It felt wrong. Pac pulled back with his eyes all squinted as if he had drunk spoiled milk. He wiped his lips hard and said, “What the f-ck?”

I laughed my ass off. “See! I told you, dummy!”

With Pac, I learned it was possible to love a guy deeply without it having anything to do with sexual attraction. I had never felt that before.

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Our bond didn’t come without its challenges and costs. We were both fiery, passionate, and dangerously stubborn. This made for feral fights. We didn’t take each other’s sh-t, and unfortunately, we also knew how to hurt each other—like no other. Our tongues were the sharpest of swords between us. Nobody could tease me like Pac. He knew how to get under my skin. He created a nickname to remind me that I wasn’t as up on my game as I acted. It was brutal. He called me “Square.” For life.

But Pac made up for the lack of male protection and care I sought in my life. Unlike other guys, who wanted to flash their jewels, cars, and cash as their value—because Pac didn’t have any of those things to display as his worth—he offered his mind, his care, and his attention. I took care of him in my own way, too.

When I first met Pac, he owned one sweater—the same one he’d worn the day I met him—two pairs of pants, and a few shirts. That’s all. Pac couldn’t hide the reality of poverty in his life. He never said so, but I could tell that getting to eat three meals a day was not a given for him. Nor were shoes that fit or getting a good night’s sleep. Between my regular jobs and cash I’d started to make in the streets, I always had some money in my pockets. To help Pac, I made it my business to ensure he was straight but not on some charity sh-t. Pac was prideful. He had standards about what it meant to be a man and stood his ground on that, in spite of how he may have been suffering. If he was made to feel like I thought he needed assistance, he would refuse support from me. And in those instances my heart withered watching him do so.

Early in our friendship, I brought some clothes to school that I’d bought him—some shirts and a jacket. But I had to be careful. As I started to show my purchase to him, I went, “Yo, Pac. Gap was having a sale, right. So, I was getting some stuff for myself, and then I saw this fly-ass jacket and I couldn’t help but see you in it. I was like, ‘This would be fly as f-ck on Pac.’” I held the jacket up against his chest. “Damn! I was right.”

I remember the biggest smile came over his face as he grabbed the corners of the jacket. “Yoooooo! You’re not such a square after all. This is dope!” He threw on the khaki jacket with pride.

I had succeeded. His sis had simply thought about him, that’s all, and happened to run across some fly sh-t she wanted him to have. Anything different, he would have made an excuse not to take it.

If I was going somewhere to eat, I’d take him with me on some “let’s kick it” sh-t, with a casual flow. Whether it was TGIF, to get a chicken box, cheesesteak subs, or McDonald’s. We had late nights at Denny’s and IHOP. Later on, when I was starting to really roll in the streets and was flush with cash, I even took Pac a few times when I went with some high-rollin’ hustlers to “upscale” dinners at Pargo’s, our spot after “a good week.” I didn’t bring Pac around often because I didn’t want to pull him into the dangers of the Baltimore dope scene—the game wasn’t for you if you weren’t from Baltimore and didn’t have your people. I wasn’t thorough like that to have him on my hip. Me, I could barely cover my own ass.

On Greenmount Avenue, where Pac lived, the dudes selling dope already saw him as a threat—a young Black charismatic male they didn’t know and didn’t like because he had an it factor they didn’t.

Pac didn’t pay their foolishness any mind. He was focused and becoming known for his brazen rap battles. At 15 and 16, he could freestyle and rhyme you relentlessly into submission. We were each other’s biggest fans, going crazy watching each other do what we loved. I loved watching him do rap battles, and he got a kick watching my dance battles. Then there came the inevitable moment when Pac tried to convince me, “You should rap. You’d be dope, Jada!”

“I don’t know, Pac.”

“Come on! Stop being a square! I’ll write a rhyme for you.”

Read More: 20 Years After Tupac’s Death: ‘A Symbol of Possibility, of Life Cut Short’

I couldn’t refuse, because Pac was so determined to have a female rap battle group. He put me and two other girls together and quickly arranged a battle for us. Pac wrote my rhyme and made me practice with him every day after school. I was horrible. Pac really tried, saying again and again, “Listen to me,” and then he’d rhyme the rhyme for me.

Can you imagine? Pac’s cadence and style were as dynamic then as when the world got to hear him. And here he was, trying to get me to rhyme like him. Pleeeasssse! He just thought my inability to do so was because I was being stubborn. Pac would be like, “What? Is your great-great-great white grandma com’n through now? Where is your rhythm? Is you listen’n to the guitars or somethin’? Get on beat, Square!”

I could never find my cadence. But I went through with the battle, and we won. I got out alive without embarrassing Pac too much, but my rap career ended there.

From Worthy by Jada Pinkett Smith. Copyright © 2023 by RedDot Publishing, LLC. Reprinted by permission of Dey Street, an imprint of HarperCollins Publishers.

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