The Winter of Whitney

by | Jun 17, 2021 | Superunknown: Stories About Songs


It is that strange eave of days between Christmas and New Year’s in December of 2018 and I am standing outside of my then-girlfriend’s apartment in Chinatown. The biting wind of a Philadelphia winter is nipping at my soft face as the signature opening 808 thumps on Whitney Houston’s “How Will I Know” coursing through my over-ear headphones masquerading as earmuffs as I wait. I turn the volume up as high as it will go and wonder whether this will be my last winter without a beard. I pace back and forth in the doorway of the narrow walk-up, repeatedly checking my watch. The local LGBT center is very strict about being on time to one’s appointments and despite the very short drive, I am certain we are going to be late. Intentional tardiness, in the form of being one of the many small ways in which partners could punish each other had become a new staple.

Though it was certainly not the first time I had heard “How Will I Know”—a song that had played in the car and at parties and on throwback Spotify playlists, it was the first time I had really listened. I know, the triteness of such a line is risky business. But bear with me. Instead of just rehearsing the sonic moves of the tune, the way it moves from drums to synth to swell to slide to more synth, I began to locate the essence of Whitney Houston’s project. “How Will I Know,” chronologically bookended by “Saving All My Love for You” and “I Wanna Dance With Somebody (Who Loves Me)” in Whitney’s oeuvre, demonstrates a well known fact: you would be hard pressed to think of an artist who understands the confluence and contours of doubt, pain, joy, and—well—love, better than Whitney Houston.

Some might argue that at its core, “How Will I Know” is a song about doubt. Indeed, Houston’s uncertainty is center stage, both in terms of lyrical and thematic content. The endless refrains of the titular “how will I know” inform us of such. But a greater significance of this song might be found in the way that it makes literal Houston’s doubt and recognizes it as a source of joy. There is perhaps a certain kind of irony in the fact that I associate this song more with an ending, the slow dissolution of a relationship, rather than the bright foreshadowing of catastrophe that is the beginning of one. You see, I was never under any illusion that I might not be trans, I was long aware of the truth regarding who I always knew myself to be. But life after deciding to transition? Well that opened up uncertainties stacked one after the other like matryoshka dolls of doubt. They ranged from the painfully banal like: will testosterone make me ugly? (Kind of no) Will my girlfriend still love me? (Also no) To the very material effects of bureaucracy: could I be fired from my job if I was outed? (Maybe, it depends). It was difficult to find joy in those moments, for the first several months of those moments, in fact. As my relationship with then-girlfriend began to disintegrate at a rapidly increasing pace, I spent more time with my headphones.

That I so intimately associate this song with the early days and months of my transition, the bubble-gummy pop aura produced by the heavy synth that could only come from an 80s song about falling in love with a boy might seem like a mismatch as the soundtrack to becoming one. But the early days and months of transitioning were in fact wracked with similarly pervasive doubt. In the same way that I wondered if it would be my last winter without a beard, I similarly wondered if it would be my last winter with Lauren. When I describe the end of our relationship, the way it faded and eroded, ultimately sublimating into something that looks like unknowing, people ask me if there was someone else. It is a difficult question to approach because the answer is—as it often seems to be—no and also yes and also no. There were entanglements (technically non-romantic) that drew our attentions elsewhere, there was the person I was in the process of becoming and the incongruity between that man and the woman with whom she fell in love. And then, of course, there was the simple fact of us.

Lauren and I broke up just shy of my five months on testosterone, the early months of spring in Philadelphia when the weather still can’t decide whether or not it’s committing to the bit. At the time, though very much unbeknownst to Lauren, in a way that was very much not her fault, I was deep in the throes of trying to figure out my gender. What I wish I could tell her now—not that it would matter very much—is that it is difficult to love someone or anyone or anything else in the way they deserve to be loved when you are immersed in the project of hating yourself. In a relationship, these things are yoked together and it is such a heavy weight to bear. In my defense—and I might not deserve to have one—hating myself in the way I did did not feel like a choice. After decades of warring with myself with such intensity, it just felt like the default setting. I did not yet know that another way of being was possible. What is the asymptote of pain you’re willing to endure in service of a relationship if at first you solve for inadvertent pain inflicted upon another and yourself as well? I used to think that’s what the calculus of loving entailed, a continuous balancing of equations.

Initially, Houston wanted her mother, Cissy, to do the backup vocals for the song, but she ultimately ended up doing them herself. Thus, Whitney is in effect answering her own questions. The backup vocals are fascinating because they don’t function solely to facilitate but to interrogate—she reminds herself in the chorus not to trust her feelings, that love can be deceiving. At the same time, that she poses the question how will I know at all stems from the fact that she knows about these things. You see, doubt and joy are not just handmaidens, they are inextricably linked. They don’t just foster disbelief, they rely upon it. How will I know, both as song and sentiment, is thus an interrogative that doesn’t end in or with a question mark, the very point is the lack of resolution.

The song fades out with endless refrains of “how will I know” after an unbelievable soar in which it climaxes from the highest “how will I knowwwww” before giving way to Russell Tubbs’s screaming, iconic sax solo. The answer is both more simple and complex than we make it out to be: You won’t and neither will I. At least not for sure, and yet there is joy to be found in that irresolvable interrogative, one that might in fact be better than the certainty you came for. Like many beautiful, messy, chaotic things, “How Will I Know” does not resolve. Not sonically, not structurally, and certainly not thematically. And yet, as much as “How Will I Know” is about unknowability, it is equally about desire. Whitney, courageous in her trepidation, doesn’t sing it like she has any doubt at all: “there’s no mistaking, what I feel is really love”.

Much like Whitney, I didn’t know and perhaps indeed still don’t in any kind of way that matters. I know that transitioning saved my life, but I also know that I lost a lot of things—not just my relationship with Lauren—in the process that have made me doubt if it was the correct choice. And while as of this writing I have only been hormonally male for 23 months, I cannot imagine a time when I was not the person I am right now, though the larger trajectory of my life to this point says otherwise. Whitney ushers the end of the song into the aural abyss with the same vibrant energy she began, a chorus of voices taking the structure of a gospel refrain as she overlays “how will I? How will I?” over it. Despite its lack of resolution, it ends in a way that is satisfying to the ear, in a way that allows us to forget the existential quandary at the heart of the tune. As such, “How Will I Know” isn’t so much invested in knowing or knowability or knowledge, but is rather preoccupied in exploring what happens when that knowledge might not ever come.

What does it mean to resolve? That we’ve gotten what we wanted? To placate amidst chaos? Or does it mean to seek and find the joy lodged within the contours of the impasse? To shout and dance and move our way through the questions that animate our thinking and perhaps indeed our lives until we come to a different understanding of what or who we are or perhaps indeed have the potential to be.







Photo used under CC.

About The Author


Jay Jolles is pursuing his PhD in American Studies at the College of William and Mary. He is an emerging writer with work in Per Contra and Pidgeonholes. You can contact him on Twitter at @jay_jolles.