How Will I Know? - Desire, Expectations, and Whitney Houston - Essay for Happy Endings

The problem with beginnings is they always come hand in hand with the unknown. At the start of something new, we expose ourselves to a plethora of possible futures with no way of knowing what future we will end up with. I begin most endeavors from a place of doubt.  I’ve lost the thread on how any of those futures can be positive and if not positive at least formative. I’m not prone to predictions of utter doom necessarily but I’m definitely filled with misgivings most of the time. I suppose it feels safer to mitigate expectations or perhaps at some point in my life I just learned that it was better to be prepared for disappointment or pain. 

I wasn’t always this way. I had dreams, aspirations, and goals that I expected to achieve. When I was younger I used to be at least occasionally reckless if not entirely hopeful. I remember diving off cliffs into a flooded rock quarry as a child with abandon, with little fear for my safety, or rather, with my fears doused with unbridled excitement and confidence in my survival. These days I worry about every choice I make as if I live on the edge of a cliff, constantly at risk of falling into uncertain and dangerous waters below. 

The idiom “don’t get your hopes up” has lived in the neighborhood of my psyche for longer than I can remember and whenever new phrases or mantras move in to make a home for themselves, she sits on her porch topless in dirty sweatpants drinking unsweetened iced tea and laughing as her new neighbors struggle to unload their furniture. They won't last, she thinks. All of that is to say, I worry that with my mindset, I force all beginnings to be bad. With each beginning I find myself asking how will I know if this will end well?

Whitney Houston sang so often about the bewildering wonderment of expectation and desire. On her self-titled first album released on Valentine’s Day 1985, one of her earliest hit singles was the dayglo synth-funk bop “How Will I Know” written by songwriting duo Geroge Merrill and Shannon Rubicam and produced by Narada Michael Walden. The origins of the song begin with disappointment. The writers originally had created the song for Janet Jackson only for it to be rejected by her team for not being “strong enough” compared to Jackson’s existing work. When the song finally found its way to Walden and Houston, something truly gorgeous was born. 

Doubt or the question of trusting one’s feelings is at the heart of  “How Will I Know.” Houston tells the listener of a boy that she dreams of, the beginning of a love that she finds exciting but also destabilizing. A strong love that makes her feel weak. She implores the omnipresent listener to answer one seemingly simple question throughout the song, “How will I know if he really loves me?” The backing vocals (sung by Mary Canty, Whitney, and her mother Cissy Houston) respond in surprisingly a less than encouraging way. “Don’t trust your feelings,” the voices reply, “love can be deceiving.” It’s interesting that the voices discouraging high expectations are Houston's own voice and that of her mother. The line between being protectively cautious and creating self-fulfilling prophecies of disappointment can be quite blurry. 

The song never answers Whitney’s question so we can imagine that perhaps it is a question that we will always be asking. In the music video, Houston wanders through a neon dreamscape set of doors, mirrors, abstract walls, telephones, and flat affect dancers. Where she is going or what she’s looking for are unclear, this is not a music video with a plot, vibes aplenty, but the plot less so. I imagine the set to be Whitney’s internal self and the dancers all represent errant thoughts dancing through her head. Whitney turns to each of the dancers seeking confirmation and finds them echoing her questions back to her, but she keeps grooving nonetheless. And the whole time she’s smiling, she’s singing, hopeful. When I watch this video and listen to the song I’m struck by how easily this song could shift into a much more melancholy place. 

I find that I’m often asking the question “How Will I Know” to the tune of a funeral dirge. My brain unfortunately doesn’t translate my thoughts into bops, there are no silver midi-skirts with matching bows, no Alvan Ailey dancers but rather grim specters of potential failure and embarrassment. There’s a lot of chanting but very little groove. No one is dancing to the beat in this noggin and if I’m to survive myself I’m going to need to change the tune to something with a little more rhythm. If I’m going to live here, god, please let me live.

I don’t want to be so cautious, so full of doubt, that I remain trapped in the confines of safety. Protecting myself from failure and disappointment, and tempering my expectations to the point that I hope for nothing has stripped all of the color out of my imagination. I need dancers! I need synths! I need dayglo graffiti walls and bows. Another idiom bubbles to mind as I write these thoughts, “nothing ventured, nothing gained.”  Ugh, I know, not exactly epiphanic, perhaps a bit trite, but who am I trying to impress? Who am I writing this for? It has to be for me! 

I began this year with a resolution, yes cringe, drag me, a resolution to get out of my own way. Despite my concerns about what I don’t know, despite all of my unanswerable questions, I want to move forward in this next phase of my life believing in my ability to navigate all possibilities. I need to trust that those possibilities will be largely not horrible. Look at me - being bold, watch me confidently taking chances. Look at my resolve.

I often forget how brave I’ve been in the past. I do shit. My partner with their at times saintlike patience reminds me constantly of how intrepidly I’ve lived my life up to this point despite my worrying and self flagellations. They remind me that I’ve done real things, and valuable things, fallen in love multiple times, and created opportunities for myself and others. Jumped off of things with no regard to what might be below. They tell me that my perspective is important. That I should trust in myself. 

Whitney Houston sang through her doubts with a smile on her face, with a head full of dancers, the whole while knowing that she may not receive any answers and I will do the same. So with that in mind I must ask you: How will I know if I’m making good choices? How will I know if I’m being foolish? How will I know what waits before me? How will I know what’s my happy ending?

How will I know if he really loves me?

I say a prayer with every heartbeat

I fall in love whenever we meet

I'm asking you what you know about these things