My relationship to the opposite sex has always been fairly fraught. 

As a woman with Asperger’s, the gargantuan effort it took to get the hang of basic human interactions left me ill at ease in the hyper-complicated world of dating and relationships; my introversion and quirks ensured I was rarely approached. Thus, I never considered myself particularly attractive, certainly not above average.

23 years had passed without prom dates, formal dates, or kisses under the mistletoe; my friends fell in and out of relationship after relationship as I mooned after a single crush. 

My dating history amounted, in the end, to a few short-lived, tepid flings.The fact that I’m naturally prone to obsession had led me into several unrequited attractions of epic proportions. Being a hopeless romantic, keyword hopeless, grew to be almost as integral a part of my identity as anything else.

“Maybe it's better for a writer” I would tell myself, channeling my misery into my latest woebegone script as I tried to resist the impulse to sad-react to pictures of happy couples on Facebook. “Maybe it’s better for a writer”… but it does wear on one. By the end of college, I was this close to loading up on some cats and declaring myself “forever alone.”

Instead, armed with an MFA acceptance and a swanky summer internship, I escaped to New York City. Upon my arrival, I decided to bite the bullet, hop on the bandwagon, and experiment with Tinder. 

Though I’d dabbled with the site back in Florida and even managed to uncover a few interesting prospects, the fact that I never had my own car got in the way of most in-person meetings. Asking my parents for a ride usually required far more awkward conversations than were worth it for even a charming stranger, a difficulty entirely eliminated by the New York subway.

At first, I figured that my high rate of mutual likes was only because men have been known to swipe right rather indiscriminately, favoring a quantity over quality approach to maximize their chances. 

But as notification after notification of a new match rolled in, the attention I was getting eventually seemed more than coincidental. At least virtually, maybe I actually had something going on! 

Suddenly, between Netflix-and-browse at my cozy Park Slope sublet and lunchtime swiping from my office in Soho, the dating pool seemed comparatively infinite. Maybe a little too infinite. 

For someone used to thinking of themselves as undesirable, the constant instant gratification of a reciprocal swipe was downright irresistible.

But how would things go once I tried taking things off-screen? 

I walked into my first date terrified that my pictures reflected my expertise at perfecting selfies more than any real-world beauty and that my messages indicated a wit and verve that would elude me face-to-face. 

Most of all, I was terrified that the man I was about to meet would take one look at my mediocre reality and immediately walk out the door. 

This, of course, did not happen. 

When swiping, I had not been paying attention to age so much as other interesting qualities, so when I walked to a wine bar only a few blocks from home, it was to meet a date who was much older than I expected. 

He went only by his initials, had worked in the film industry, and had traveled the world. The vibe between us at first felt more friendly than romantic. He's an experienced, worldly guy, what could he possibly see in someone so nervous, vulnerable, and wayward? 

So it was a surprise when he started commenting on how pretty I am and especially when he asked if I'd mind him sliding over to my side of the table.

By putting us at a one-on-one level from the start, the artificial start to these courtships diminished many of my surface weaknesses and led men to give me the benefit of the doubt. Most seemed to find me attractive & intriguing; many wanted to see me again.

And in a city so vast, with a summer so aimless, deliberately looking wasn’t the only way I was amassing gentleman callers. 

For the first time in my life, I found myself being constantly approached at clubs, bars, and galleries, meeting men who quickly indicated their interest after I so much as gave them the time of day. 

If someone did fail to message me after a date, the unlimited pool made it easy to move on. In fact, it was usually a relief. For I am, in most circumstances, far too passive of a person and my relative inexperience means I have not had occasions to master the gentle art of letting people down.

While I strictly upheld certain physical limits, I sometimes found it easier to agree to make out than come up with a reason to refuse, and too often would simply ghost or evade suitors rather than face the prospect of rejecting someone head-on.

Of course, as a woman, the differing expectations between me and the men I interacted with did occasionally prove problematic. 

Overt perverts, sleazeballs, and fuckbois of all varieties could be easily unmatched. More insidious were the men who seemed (over text, at least) reasonable enough to meet in person but upon some actual interaction clearly only had one thing on their mind.

Though I never experienced any outright aggression, some men were obviously dissatisfied when an evening together failed to culminate in the experience for which they’d wished, even to the point of unmatching me.

This problem was only a specific facet of how difficult it was to get a read on who was worth getting to know via text alone.

Attraction, for me, is all about someone’s energy and charisma more than what specifically is said or how someone looks, all the things that proved impossible to ascertain from virtual conversation.

Was someone who messaged back quickly or often too aggressive or merely trying to indicate a sincere interest? When do you finally give out that number, to whom? 

How strange it was to exchange virtual sweet-nothings with one match and then going straight back to the swipe screen or to repeat the same story to another. I assuaged my guilt with the knowledge that each of them was probably doing the same.

But I did find a certain relief in the fact that I would almost literally never have to be alone if I didn’t want to be even without many close friends in the city. 

Whenever I felt like a casual boredom-fueled endeavor or even just not paying for my own drinks, all I had to do was start swiping or messaging my stable. It seemed my days of spending Friday nights drenched in self-pity at my laptop were finally gone for good.

And oddly enough, consorting with the locals on Tinder actually proved a decent way for an unattached newcomer to make one’s way about the city, to discover free museum nights and concerts, get myself invited to hip bars and rooftop parties, trending restaurants, and crowded picnics in the park.

There were certainly plenty of interesting one-offs. There was S, the gangly, vegan, schoolteacher with whom I shared a lychee martini and a subdued night at an outdoor production of Richard III. He said afterward that we should meet up again sometime. I agreed. We exchanged a few texts but never did.

There was A, toned and handsome, in for the weekend, who seemed to expect Tinder to deliver him some booty with the rote predictability of something like Uber. 

We shared a nice walk over to his place, and I get as far as his bed before realizing we may have differing ideas about what constitutes "interesting shenanigans". He's very polite about our divergent understanding. I suppose it was flattering, in its own way.

But of those who made it to second date status, there weren't many. 

I eventually see the first man one more time. With his formerly flowing hair chopped off, he seemed so much older somehow, almost like Sampson, a certain power lost. Or is that I've become that much more jaded? When I visit his smartly decorated, but conspicuously empty apartment, I feel almost sorry for him.

Another contender, T, gained ground towards the beginning of the summer. We started at a cafe, took a lengthy walk through Prospect Park, and finished up with some cocktails at Quarter Bar. He's sane enough, clever enough, funny enough, good-natured, works in advertising.

I wouldn't go as far as saying there were sparks, but there seemed to be at least potential. When I met him for our third date he claims not to be drunk, but he seemed at least tipsy. I don't actually begrudge him this; being the sober one gives me the upper hand. 

He invited me, somewhat persistently, to accompany him back to his place, insisting that if I did, things wouldn't have to escalate.

Though it sounds a little sketchy from those details alone, I believe things wouldn't necessarily have taken a worrisome turn. In hindsight, I almost regret not going for it and going with him. But at the time I think I was looking for an excuse to write him off.

And then, of course, there was M; the closest I came to an actual relationship.

Our first date was above par, first visiting Bar None close to Central Park, then taking over the jukebox at Coyote Ugly. Of course, maybe I should have been worried, rather than flattered, when he confessed a few drinks in that he was already halfway in love with me.

But with several literary endeavors, a job at a non-profit, a schnauzer puppy, and even a minor political office, he seems impressive on paper. Again, there seems to be potential.

It was the constant, excessive professions of affection that began to emerge from him that turned me off, made everything between us seem much too serious. 

There are many times I tried to explain this, and sometimes it seemed to sink in, but only briefly. Whenever I tried to pull away, express even a reasonable reticence, he would only come on that much stronger.

His attempts to be "romantic" eventually came across as just as hollow and desperate, even sleazy. His constant reassurance felt somehow patronizing. 

He insisted, despite my protests, on buying me an expensive necklace; and though he then insisted I didn't owe him, I hated feeling like I did. I couldn't spend time with him without feeling like I was in the process of being brainwashed. 

He claimed, too, that we were friends first, but his interest in me as a person always seemed to take a back seat to his unwavering intent to seduce me. I couldn't get a sense of him besides how much he wanted me.

Eventually, he asked me to be his girlfriend. The question was obviously making me uncomfortable, but he continued to pursue the subject, asking again and again until I felt cornered enough to agree. He began, often, to bring up the future, conjuring visions of us together for the rest of our lives.as it so bad of a fate?

Maybe not, but it certainly felt excessive.

"What did you do all day?" I ask him the next time we hang out.

"Wait for you to come by, mostly" he responds.

That wasn't the answer I wanted. It was far too much power. I was in no place to be someone's future, someone's world. I left, abruptly, one last time, never to return, feeling heartless for following my instincts: to keep a distance, to stay guarded, to stay safe. 

Worst of all, I felt heartless that I'd made it ten times worse by trying to give him a chance.

With all of them, something seemed to be missing. Maybe chemistry, maybe trust… or maybe the problem was me. 

Somewhere along the way, I had begun to view it all as a grand experiment, a silly pastime as I waited for my emotional and academic burnout to lift and my passion to return. 

I had continued swiping less in the hopes of finding a decent match than as a near-compulsive way to fill the hours, choosing to meet someone or not almost arbitrarily based only on who asked when. Somewhere along the way, I had stopped giving anyone a real chance.

Maybe I just wasn’t over my latest hometown crush. Or maybe, without a sense of grounding, I wasn’t actually ready for love.

Instead, I was quickly becoming addicted to the thrill of being single and of meeting strangers, which only served to heighten my habitual avoidance of physical and emotional intimacy. Why start letting down walls for Mr. Pretty Decent when Mr. Perfect might still be only one swipe away?

Irony of ironies, my very pursuit of it seems to have done nothing but get in the way of finding the one thing I’d set out looking for: an actual relationship filled with real intimacy and love.

It certainly seemed a dangerous rabbit hole to wander down, especially given some close-call drunken misadventures, as well as an increasingly time-consuming distraction. Besides, realizing how easy it was to wound and to be wounded had taken the fun out of it all. 

So come fall and the start of my MFA program, in an effort to get serious, I deleted the app altogether, ending my strange journey that much more hopeless than before.

Well, there's always the cats, right?

[Feature Image Courtesy Pinterest]