Please Do Say Forgive Me

Chandra Steele
4 min readFeb 28, 2019

Tupac’s Apology to Madonna

Stolen words of love

In the smoke of a breakup, whether we loved the person or didn’t even like them that much, there emerges a vision of them one day realizing the error of their ways. If we allow ourselves to follow it too far into the thick of delusion, we imagine a detailed accounting of feelings, an explanation of events that puts the weight of responsibility on them, and full absolution for us of any fault in beauty, character, or action.

To manifest something so seemingly singularly impossible you’d have to be Madonna. On January 15, 1995, Tupac Shakur put pen to paper in prison and told her why he had ended their relationship, expressed the fears and doubts that had stood in his way, proved and pledged an improved self, put his worries for her safety on an even plane with his, and spoke of his hopes for reconciliation.

The letter is two pages, with an addendum on a third page and a small, sweet heart at the end. Tupac put the time at the top. In the time before timestamps, it’s a detail to be parsed. 9:30 a.m., the clear-eyed morning, an hour of purpose. It is carefully and beautifully written, in what it says and in how it looks. Tupac’s handwriting is looping and lovely, almost feminine. He addresses Madonna as “M.” It is a large M, with the final line swooping up and then dipping two full spaces of lined paper below it; an M worthy of Madonna.

“I’ve waited a long time 2 finally write this,” he starts, immediately putting a real part of himself, that 2, into it. What follows is his soul placed plainly on the page. He describes his mindset at the time that the two were seeing each other. Not as an excuse but as a point of orientation. They dated quietly, when he was a man who was just garnering his debt to the community that made him and she was a sex symbol that belonged to the world.

Celebrities are separated from us by our perception of their godlike attainment of what we’re supposed to want: fame and money and sex. But when Tupac refers to their relationship, he uses words of humanity and humility. “I haven’t been the kind of friend I know I am capable of being” is how he frames the apology. It’s an empathy that some never access within themselves, no matter how many classes they take in unlocking their chakras. Later he tells Madonna, “I offer my friendship once again, this time much stronger and focused.”

The letter is, above all else, generous. Even when he mentions an egregious comment Madonna made in an interview — “I’m off to rehabilitate all the rappers and basketball players” — he does so only to elucidate that the words were a blow to his heart and ego that resulted in his saying things he came to regret.

What’s more remarkable than what’s written is what isn’t. Tupac does not overstep the bounds of being an ex-lover. He does not push a selfish agenda. He has the wisdom to balance what he wants with what is warranted after leaving sans explanation. He does not burden her by asking for her forgiveness.

There are more words, four passages worth, but they are a literal blur to us because an auction house scrubbed them out of their images so that they could sell them without giving too much away first. This letter is a precious artifact for Madonna, a holy relic for all of us that want to believe that such a thing could exist. And like any such object, it was stolen and came into the possession of someone who falsely thinks its value lies in a dollar amount.

This type of letter is so rare that even Madonna only has one and she sued to try to get it back. A former friend of hers claimed she came by it along with other possessions in the course of their friendship. In the affidavit Madonna filed she states that she never gave it away. Her written testimony notes that she had a specific memory of reading it: “In particular, I remember that he apologized to me.”

The letter does not appear on an archive of items on the auctioneer’s site, though other items from that lot do. I contacted them in an attempt to find out what happened to it but never heard back. I like to think that Madonna bought it, that the love-lettered sheets of looseleaf are with her again. No matter who has it now, the chances that you or I will ever have anything of our own approaching it are infinitesimally close to 0.

The closest I have come is a Facebook Messenger message. It was sent to me late one spring night, its timestamp telling me so and my opening it the next morning marking exactly when it was seen. I remember thinking I should take a photo in case our digital connection was ever severed. But in the small glow of satisfaction I got from reading it, I stood up and decided to take a walk in the sunshine.

Weeks later, I needed more than just the fractured collection of words I remembered, I needed the reassurance of their exact phrasing even if they weren’t exactly an apology. I opened Messenger to discover that my letter, which it can’t even be properly called, had disappeared, too. The person and I were no longer friends by Facebook’s definition. And then one day just as inexplicably we were again. I screenshot the message and saved it to my camera roll. I thought of Tupac’s words: “It’s funny but this experience has taught me not to take time 4 granted.”