He was that attractive kind of quirky, just odd enough to keep it interesting. I liked him almost immediately. The New Yorker in me was relieved by the self-deprecating humor and unapologetic honesty. He added a healthy dose of cynicism to the enthusiastic San Franciscan bar chat. Initially regretful, I grew intensely grateful that my friend had dragged me out. And we kind of hit it off. The type of flirtation where there was no doubt we were getting along, but the likeliness of it being as “friends” or “something more” was, really, anyone’s guess. Over deliciously late-night burritos the topic of meeting people (romantically) in San Francisco entered the conversation. After mutual complaints were vented, Quirky interjected “at least online dating makes it easier.”

I had been an adamant, vocal opponent of online dating since the concept first hit the scene. The romantic in me shuddered at the idea. Not that I was a prototype for healthy, intimate relationships. I hadn’t had a serious boyfriend in over 3 years and my current version of “relationship” could best be described as a hang-out-with-a-make-out type situation, which, inevitably, grew to be nothing more than a terrible decision. That said, I was sure online dating was reserved exclusively for the desperate and socially inept. And now a man, to whom I probably would have committed at least a few hard spent weeks of awkward text-tagging, was telling me that he was customarily taking girls out on legitimate dinner-and-a-movie dates after nothing but a quick internet browse?

That was two years ago. I have since had 4 committed relationships, too many dinner-and-a-movie dates to count, and nothing short of a PhD in small talk. All thanks to the beloved Internet and a noncommittal dating website. In less than two years, I went from being — what seemed like — eternally single, to essentially having exclusive boyfriends hand-served on a platter. It was a welcomed change, at first. But after what felt like a relay of monogamy, each leg lasting about 3-5 months, one of us would inevitably break it off, citing the ever-popular and always ambiguous explanation: “it just wasn’t ‘right’”.

To be clear, it’s not like every meet-and-greet turned into an instant commitment. There were the usual culprits: nothing like their photos, painfully quiet, or simply good people you just knew would never be more than a nice conversation. There was one very attractive man, for example, who had a great job, was a fine conversationalist, had no red flags, but there were simply no Clicking Moments. In every exchange we were just a tad misaligned.

You need the Clicking Moments. When I met my first online-initiated boyfriend, things fell right into place. I knew it was good when I realized I hadn’t asked any First Date Questions — those in the vein of: “Do you have any brothers or sisters?” or “What was your college major?” No, our conversation flowed, every topic leading to a hearty discussion, no time for the standard Q&A. Disagreements didn’t breed silence, they bred laughter and debate. And agreements came frequently, accompanied by flirtatious smiles and longs nods. And then it started. We liked doing similar things, and clearly kind of wanted a relationship, or why else would we have put ourselves through the online ringer? So we began dating, fairly seamlessly, excited by the opportunity of love, a pleasant dinner companion, and fairly consistent sex. Now, for the statistically inclined, for every ten dates I had, about one would end like this.

These relationships, however, were loosely knit on common interests, like “eating burritos” or “indie rock”, or Mad Men. Don’t get me wrong, there were some strong connections, and spending time together was fun, but something deeper always seemed to be missing. In each one, we met each other’s friends, took trips, spent hours by each other’s side. It seemed though, that despite the time put in, there was some barrier to a more intimate connection; a feeling that we ultimately weren’t opening ourselves up enough to affect one another, to change with one another.

Relationships in my early twenties weren’t like this. For good or bad my personality was basically co-developed with my college boyfriend, who I dated for 4 loving years with 2 more years best described as “it’s complicated”. The relationship after that was two years of, similarly, maturing together. Both of these men grew to know me inside and out, and have since become close friends. So after a string of relationships that seemed to have strong foundations, but no ability to deepen, I became disturbed. My skepticism of online dating reemerged, in new form.

Granted, it’s not that I could have, or should have, made it work with every guy I dated online. I visited New York with one of them and he refused to drink deli coffee — gourmet only. We’re in NY and he wouldn’t drink coffee from a deli? Unacceptable. Clearly, some just weren’t right and it often took a few months to realize that. But for each, the sparks that created that initial connection did not develop. In times of conflict, or imperfection we didn’t work at understanding, we simply cocked our heads. We exposed inner monologues, guilty pleasures, deep secrets, but it was always two individuals observing one another, like an exhibit, constantly wondering how interesting it really was, always wondering if we should check out the next one instead.

My first reaction was to blame this inability to meld on the Internet, and the mirage of an endless dating pool it created. But as the pattern emerged it was clear I also had to take some blame. The Internet was an enabler. Before I started dating online, at around 30, I had been single for almost 4 years. During that time, as we are now so often encouraged in our 20s, I focused on Me. I moved across the country, got my Masters degree, found a job I loved, and developed a family-like group of friends in a new city. I felt proud of the life I had created. The idea of compromising that identity, or settling for someone who didn’t meet the same standards to which I’d held myself, seemed out of the question. So, after overcoming the initial awkwardness associated with creeping online profiles, I was secretly elated by the possibility that this endless pool of singles made it realistic to eventually find the person who would fit just right — scroll, scroll…

I was in the now common and complex situation of having (seemingly) infinite options with unachievable standards — a generational problem not isolated to online dating, but certainly highlighted by it. Inundated with options, I had forgotten the butterfly-in-my-stomach feeling of meeting someone on the street, striking a good conversation, and thinking something kind of magical had happened. That deep appreciation for a moment and the serendipity that created it. What became clear from dating online was the sudden lack of appreciation, and how natural it became to give up the fight. It was easy to take things for granted when at any moment you could log back on and continue browsing.

Recently, I had a breakup that acutely reminded me of the danger in this mindset. We had dated for about four months, spent most of our free time together, and hit it off without question. By this time in my online dating stretch I felt confident that I had learned to appreciate what mattered and give things a chance. He, on the other hand, had just come out of a six-year relationship and had never dated online. I was caught completely off-guard when he hesitantly, and suddenly, decided, “it just wasn’t right.” After mutual tears were shed, he explained, “it’ll be OK, after all I’m just a guy you met on the Internet.”

It’s scary to try and work at something new when all the pieces aren’t an exact match. It’s much easier to shake your head and move on to the next — to avoid compromise, preserve your Self, and hope that the next one is perfect. But we may back ourselves into a corner when so much of connection comes through struggle, conflict, and compromising the idea of perfection enough to actually create it.

That quirky guy I mentioned at the beginning of the story — he now lives across the country, but over the past two years (though never at the same time) we’ve confessed a secret longing for one another, grown deeply as friends, and now talk at least once a month about everything in our lives. The four committed online boyfriends? I’ve since greeted a few times on the street in unavoidable situations, but they would be the last people I’d reach out to if I needed something. Not because things went down in flames, or because they’re bad people, but because we never really trusted one another. Or, more accurately, we never really trusted in one another.

I haven’t completely stopped dating online. I still get excited when I see a promising message. Online dating isn’t the problem. Like most modern-day solutions, it makes things easier. But as we’re so often reminded, good things don’t come easy. The challenge today is to not be tempted by what’s easy in lieu of what’s real; to appreciate what’s around us. To be courageous enough to let the differences affect us, and the conflict teach us. To not just expose all of our edges, but be strong enough to let ourselves be shaped; brave enough to let ourselves be vulnerable.