I will admit something that still feels tender to say out loud: I have never been in a real relationship. I have never truly dated, never been seriously asked out, and if I am being honest with myself, fashion has always been somewhere in the middle of that story.
I do not get dressed casually; I get dressed intentionally. Some days that looks like a SHEIN cropped dress shirt paired with tailored trousers that hug my waist just right, and other days it becomes a semi-femme moment—a denim jumpsuit, a bodysuit, or glossed lips, or a subtle beat of makeup using m.ph by Mary Phillips, Charlotte Tilbury, or Estée Lauder foundation. I move between masc and femme the way some people switch playlists: instinctively, depending on my mood, the weather, or who I feel called to be that day.
Over the years, I have been told that I am “too feminine,” and in almost the same breath, I have been told that I am “not masculine enough.” Those comments stayed with me longer than they should have. Dating, especially as a Black gay man, comes with unspoken expectations about what masculinity should look like—steady, legible, uncomplicated.
For me, dressing up has always been about alignment. Yet when I get dressed for a date or a meetup, the process is instinctual rather than strategic, because I am asking myself a far more intimate question: How do I want to feel tonight? Sometimes I want to feel powerful, sometimes delicate, and often I want to embody both at once.
I remember one meetup vividly. I wore a black cropped top with my Good American high-waisted jeans and Steve Madden black boots, and I felt incredible—confident in a way that was rooted rather than performative. Midway through drinks, he leaned across the table and said, half-jokingly, “You have great energy… I just don’t know if I’m supposed to be the masculine one here.” In another instance, I was out with friends when a guy had been checking me out all evening, only to look away and act unfamiliar once he clocked the full intention of my outfit. I had an all Guess Canadian tuxedo on that night.
The final meetup that stayed with me for the longest time. I met a man in my industry for drinks in Hell’s Kitchen. I arrived in a crisp dress shirt tucked into Lee high-waisted jeans with black loafers. As the conversation unfolded, he casually mentioned that he was seeing someone and had been married multiple times. When I began sharing some of my own dating experiences, how many men I encountered were still hesitant to genuinely get to know me, he listened briefly before offering a blunt response that lingered longer than the cocktails: “Maybe you’re the problem.”
I have tried what everyone suggests when love does not arrive organically. I downloaded the dating apps, uploaded my best photos, crafted bios that felt charming yet honest, and swiped with hope. The result was not dramatic heartbreak, just emptiness. Even when matches happened, conversations rarely moved beyond surface-level exchanges, and I began to question whether my outfit choices are the main problem.
Offline, the pattern has not felt much different; there have been moments when I gathered the courage to ask a man out, only to be politely rejected, and other times when I allowed myself to develop feelings and express them honestly, only to hear that I was appreciated “as a friend” but not seen as a partner. Each time, the message felt subtle but familiar—that I was enjoyable in proximity but not chosen for something deeper.
There was also a man I met at the gym, a flirtation that unfolded so intensely it felt cinematic in real time. For weeks, the chemistry was intoxicating, and his charm made my days feel electric. But when he moved abroad and eventually built a life with someone else, I realized I was not heartbroken over him; I was mourning how he made me feel. I even tested my desirability outside my usual geography, solo traveling to Barcelona and Portugal with the quiet hope that perhaps distance would shift something. Instead, I found myself beautifully dressed in plazas and along coastlines, moving through romantic scenery without anyone approaching me in the way movies promise is possible.
Sometimes, I observe my friends’ dating lives and I ask myself whether I truly want to stand in their shoes.I have also watched people remain heartbroken from past relationships, still texting their exes or revisiting conversations that never fully close. In sessions with my therapist, we unpacked how attachment can sometimes disguise itself as love, and seeing those patterns made me realize that I do not want a connection built on lingering attachment or nostalgia. I have also noticed that even some people in long-term partnerships grow visibly uncomfortable when marriage enters the conversation. Watching that has reminded me that proximity is not the same as preparedness, and longevity does not automatically equal intention.
Then there was the tarot reading in Arizona, when the reader told me she did not see me in a relationship. At the time, it felt ominous, but after watching Solo Traveling with Tracee Ellis Ross and hearing her say, “I am responsible for my own happiness,” something shifted. I realized happiness was not waiting for me on the other side of partnership. I am happy with my own company.
After years of trying and replaying conversations in my head, wondering whether I had been “too much” or “not enough,” I chose stillness. I began dating myself with intention, learning that solitude is not rejection but refinement. I do not want love that lingers out of habit or fear of being alone; I want something chosen in clarity.
When I lean into softness or silhouettes coded as feminine, I am not abandoning masculinity, I am expanding it. I am claiming a version of manhood that includes detail and delicacy, and that understands desire is less about dominance and more about presence.
The truth is, I do not want to be chosen for the version of myself that feels digestible. I want to be loved in full resolution. Dressing up may have narrowed my dating pool, but it has also clarified it. The people who linger are the ones who see my fluidity not as a contradiction but as depth—and until someone can stand beside me fully, I will continue standing beautifully on my own.
The post How Dressing Up Shapes My Dating Life appeared first on Essence.
Author: Akili King
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