On the precipice of forty, a time when many are comforted by the cocoon of family life, I found myself navigating the unfamiliar territory of online dating. Without a past marriage or children to signal a history of commitment, I sometimes felt stamped with an invisible label: Something must be wrong with her if she’s never been married. In the silent corners of society, divorced individuals at least carry the badge of having tried. The scars of a partnership that ended, to some, are preferable to the blank slate of someone who appears non-committal.
As I embarked on this digital journey, I hoped the parameters of judgment had expanded, or even ceased to exist. Perhaps the world had grown kinder, more understanding that love and commitment aren’t solely housed within wedded confines. Maybe we’d grown more attuned to the diverse ways people find fulfillment, understanding that many consciously embrace—and thrive in—solitude.
I chose Hinge for my dating app adventure, not with the starry-eyed hope of finding my lifelong partner (though that would’ve been a welcome surprise), but more as an anthropologist in the land of modern love. Opting for just one platform, I assumed there would be considerable overlap among the various dating apps. I was curious: had the landscape of human connection shifted in this age of swiping left or right? What was the rhythm of romantic discourse in a world mediated by screens?
Whenever I spoke to single friends, who lived in bustling metropolises and smaller towns, a collective lament resonated: “Dating is just so hard.” I sought to understand why this refrain was universally sung.
My digital voyage began in San Francisco, the city I called home for nearly a decade. Like many others immersed in metropolitan dating, I soon felt the quandary: the allure of perpetual possibilities, and the paradoxical inertia of ceaseless swiping.
Yet, as I embraced this digital sphere, I also unexpectedly found a renewed sense of openness to people, as if downloading the app had broadcasted a silent message to the universe. I started meeting potential romantic interests organically, friends suddenly turned into matchmakers, and a chance meeting at a Big Sur cafe segued into an impromptu romantic weekend.
Online, though, my journey seemed to become a mirror, reflecting insights about the modern dating culture and sometimes uncomfortable truths—or rather perceptions—about myself. I lingered in the comfortable digital dance of texting too long, allowing days to pass without transitioning to a real-world meeting. I could see my fears staring me directly in the face, and the question loomed: Was I really ready for intimacy, or was this simply a social experiment?
Some men had an interview-like approach to dating, seemingly keen to only gauge my sexual proclivities and perhaps, more directly, how many dates were needed before we could consummate a sexual relationship. Others broached non-monogamous relationships, a terrain I discovered quickly was not for me.
In one instance, after I declined sending additional pictures to a man, he audaciously texted me a selfie of another woman he was seeing (undoubtedly a much younger woman than myself) with an added, and mildly offensive, note: Just so you know. This is your competition.
Others sensed the anthropological nature of my intentions for online dating, suggesting that I was taking on the role of a therapist. One man, who I invited over for the first date (something I would never recommend to others), said I possessed witch-like qualities but good ones — leading to a fleeting idea to create a blog about online dating, and calling it “The Good Witch.” Another remarked that despite my childless status, I radiated a maternal energy that he didn’t find particularly sexy. The contradictions felt boundless. But it wasn’t all critique and complexity.
In the midst of these varied interactions, I stumbled upon genuine souls, earnestly seeking a nourishing partnership. And then there were those with whom I felt a kinship, individuals who, under different circumstances, could have seamlessly transitioned into meaningful friendships. With a few, I felt an urge to assist in enhancing their dating profiles, recognizing that they were so much more appealing in person than they appeared online.
I began to notice other unexpected positive side effects of online dating. While exploring this new landscape, I found that dating actually bridged deeper connections with women akin to me: single, on the cusp or in the midst of middle age, and delving into life’s profound questions masked by online dating’s facade.
In my San Francisco apartment, I began hosting women’s groups. These meetings drew women at similar life junctures. Our evenings ranged from intimate exchanges about our personal journeys to sessions with coaching friends and spiritual guides, deepening our collective exploration of authenticity and connection. But of course, because we were a group of women in the same demographic who were all online dating, there was some awkward overlap with the men we were connecting with. I began to realize this was yet another predicament of the modern dating conundrum.
In addition, dating allowed me to channel my experiences into a creative outlet: a private Facebook group, “Women’s Voices.” With close to 1,000 members, this community became a sanctuary for open dialogue. My posts, deeply rooted in personal reflection, tackled themes from the elusive dance of romantic chemistry, navigating rejection’s two-way street, to realizing that true connection can’t be manufactured.
During the pandemic, as I transitioned from San Francisco to southern California and eventually to Santa Fe, New Mexico, my online connections became vital touchpoints to the outside world and guides to my new surroundings. The enforced isolation of the pandemic forged a distinct dating backdrop, amplifying our inner anxieties and fears without the usual distractions. Against this setting, the people I met online unveiled deeper vulnerabilities. I did, too. And interestingly, because we were limiting our interactions during the pandemic, this forced people to focus and to acquaint oneself on a deeper level. One gentleman suggested a charming return to penning letters as a way to get to know each other. Zoom dinners often saw me self-consciously chewing as a digital face observed. I encountered a spectrum of individuals—from a Malibu firefighter to a man who once served time for drug dealings, and divorced dads whose devotion to their kids deepened my appreciation for my own father. Gradually, I discerned and appreciated the enriching tapestry of human connections that online dating unfolded for me.
About eight months into my online dating journey, while in southern California, I encountered a significant turn: I met a man who I had genuine feelings for. Like me, he grew up in the Midwest, transitioned to city living during his adult years, and now, in his forties, sought the charm of smaller towns. And, there was a burning chemistry between us that I had found was often missing with other matches.
However, despite gaining some proficiency in the initial steps of online dating, I was not well-equipped for deepening a connection or fostering intimacy and trust. A string of misunderstandings, heightened by personal challenges he was facing at that time, led to an abrupt end, leaving me deeply disheartened. A month later, I attempted to re-establish our bond, but our relationship remained unstable. Despite my profound feelings, I struggled to articulate them, inadvertently appearing distant, aloof, and self-centered when really I wanted to be emotional, connected, and effusive. In one of our last exchanges, he noted, “You need to learn how to communicate.”
This experience became a reflective moment, highlighting my underlying vulnerabilities and the skills I was missing in fostering close relationships. My many years of valued independence revealed an unforeseen challenge: a difficulty in navigating emotional complexities, voicing my needs, addressing my letdowns, and devising ways to remedy them. Seeking guidance, I turned to a highly recommended therapist from the Bay Area, who accommodated virtual sessions through the duration of the pandemic. We methodically explored the depths of my emotional hurdles, working towards understanding the barriers that kept me from true intimacy. I emerged with renewed insight: I held a genuine aspiration for a future partnership and I was working on building my intimacy toolkit. Despite the inherent challenges of relationships, I began to recognize and embrace the promise and growth that love brings.
Relocating to Santa Fe presented a different online dating environment: fewer options worked well for me and created an opportunity to develop relationships quickly. Here, in a period of two years, I found myself in two successive relationships, both men I had met on Hinge, and each of the relationships illuminated my blindspots and glaring patterns: my struggles with communication and emotional containment.
Despite these revelations, while I am currently single and only sporadically do I jump online seeking a match, the only dating journey over the course of nearly four years created a gateway to deeper self-awareness and understanding. I looked within, tending to long-neglected emotional scars. Intense reactions and emotional mismatches propelled me to explore their roots, and in the relationships that I had in Santa Fe, while they weren’t sustainable, I was able to practice new skills and a greater sense of self-awareness.
Do I still harbor hope and desire for a relationship? Absolutely. Do I believe in the efficacy of online platforms? Yes, but with a caveat: they do serve as a tool to date, but mostly they provide a unique portal to our rich inner terrain.
In the world of digital romance, I remain steadfast in my optimism. The quest isn’t merely to find love, but to understand oneself through the process. Modern dating isn’t a monumental task but rather a misunderstood art. The essence of love and connection isn’t bound to an app or a swipe. It’s an inward journey, and as we embrace our personal evolution, the universe reciprocates with reflections of that growth. It’s not just about finding love; it’s about understanding ourselves along the way. The digital realm is just a tool, guiding us on this journey of self-discovery. In an era dominated by screens and external distractions, we often overlook the most profound connection—the one with ourselves.
