Cupid is Not Online

It's over. After 2 years of intermittent meet-ups and occasionally awkward conversations, I have finally extricated myself from the online dating world. I had never even considered trying it out in the first place, but in today's day & age, such an approach to sociability and love-seeking has become more acceptable (and readily apparent) than ever before. To me, it has always seemed like too much of an impersonal and unpredictable approach to meeting people, especially given the level of dedication that the process entails and the amount of work that you have to put in. However, at the recommendation of two friends of mine that had good experiences on a particular dating site (and became involved in semi-serious relationships), I decided to take the plunge myself to see what opportunities would arise. What transpired in the ensuing 24 months was a series of bizarre meet-ups and interactions that ran the gamut from the excruciatingly awkward to the too-good-to-be-true...

Now...keep in mind that, despite the fact that I was on this dating site for a span of two years, I would sporadically disable or delete my account for 4-5 month intervals. When consecutive dates wouldn't work out (either due to their lack of interest or mine), I would suspend my account altogether and re-assess how I presented myself in these meet-ups. Sometimes I would try to "dial it back" and not be as extroverted or proactive, while in other situations I would take the opposite route and try to woo them as much as possible. Both tactics often tended to backfire for me, and so, the time eventually came to delete my profile and never return.

My initial encounters started promising enough, with active back-and-forth messaging between me and several interested girls. While the first couple of dates were more casual and mediocre meet-ups (going out for coffee, "happy hour" drinks), a particularly promising girl eventually stood out among the rest - a cute Filipino girl named Alex. We had very pleasant conversations online, and one night we decided to have dinner together. Since I had never tried Filipino food before, we went to a favorite restaurant of hers that served authentic cuisine.

The dinner went well. Both of us awkwardly tried to get to know each other while we ate: the adorably shy Alex geeking out over her career as a science teacher, and me trying to be engaging while doing my best not to eat ravenously in front of her. Unbeknownst to me, the portions at the restaurant were way too small for my liking, and I had to pace myself throughout dinner so that I didn't come across as a raging glutton. I was still hungry after I finished my entree, yet Alex had barely touched her food and seemed consistently anxious throughout the meal.

Then the check arrived.

The waiter gently placed it on the table - more on her side than mine - and left. I glanced at the check...then I locked eyes with her. Alex smirked ever so subtly as the slip of paper lay on the table for several seconds...and she didn't even make the slightest gesture to grab it. I'm very much of the mindset that men should always pay during dates (and from the get-go, I was ready and more than willing to do just that), but it seemed to me that Alex was just a bit too comfortable with this sentiment. Rather than try to offer to pay in the most half-hearted way possible, just to make me feel better, she kept her hands in her lap and eyed me constantly, waiting to see a credit card or a couple of dollar bills leave my pocket. Even the most subtle grab of the check would've made me feel more at ease, but Alex's decision to remain inflexible when it came to paying gave off the vibe that she was high-maintenance. Needless to say, Alex & I didn't go out again.

While this wasn't an excruciating date by any means, I did experience one several months later that was, quite simply, atrocious.

It started one rainy weekend in the city. The kind of rainy weekend that makes you stay inside for days, flipping through channels and bingeing on junk food. One evening, I started chatting online with this petite, dark-haired girl named Brianna. We clicked so well during that first conversation that we spent the following three days messaging each other for several hours. She seemed genuinely interested in me, and I was very much interested in her. We both admitted to each other that we desperately wanted to meet in person, to see if this passionate vibe that we showed online would translate into a fruitful, in-person dynamic. Since I had learned that she was a fan of campy horror films, I asked her out to go see Scream Blacula Scream at the MoMA - followed by a picnic in Central Park. I brought a blanket with me and bought a cupcake to surprise her.

An hour before meeting her, I decided to catch some of the newer museum exhibits and have some time to relax by myself. When she arrived, she texted me and told me she was waiting outside. I made my way out of the galleries and thought about what she would look like in person, and whether it'd be instant sparks upon meeting her. As soon as I stepped outside and my eyes met hers, however, I knew that my expectations had been way off the mark. The Brianna waiting for me outside of the MoMA couldn't have been more different than the Brianna that I synched so well with online. This girl was cold, overtly serious and practically mute. After the movie ended, she barely talked to me as we walked towards the park. If I tried to make conversation with her, she would only respond in monosyllabic phrases that would completely halt any semblance of a rapport that I was trying to develop. We walked side by side for ten blocks, and I felt like I was reciting a monologue out into the open air. She simply did not contribute an ounce of engaging dialogue throughout our walk (and even seemed quite content to do so).

When we entered the park, I decided to try to charm her one last time and see if I could soften her detached & disinterested mood. I took the cupcake box out of my bag and handed it to her, and she immediately opened it to reveal a red velvet cupcake inside. Since the box had been inside my bag for a couple of hours, the cupcake's frosting had dropped to the side - which impelled Brianna to utter immediately: "Oh, good...a frosting-less cupcake." At that moment, I buried my anger deep inside and, instead, chose to make light of the situation. However, as soon as we exited the park a couple of blocks later, I immediately asked her in what direction she was heading, and I quickly went the opposite way and took the train back home.

These scenarios are, of course, mere isolated moments out of a two-year span where I did end up going on some wonderful dates. I saw Rififi with a beautiful Hispanic girl at Film Forum one breezy March evening, while in another occasion, I went out for breakfast one chilly winter morning with a super smart & funny South African girl. I do cherish and look back fondly on these encounters - however brief they were - because they allowed me to overcome a built-in sense of trepidation that I developed during a period of time. Rather than having embraced a resigned approach to dating and let life run its course, I opted to try to create my own future and dictate the path that I wanted to go towards.

Yet it turns out that things don't really work out that way. At least, not for guys like myself. These brief but vibrant dates were definitely pleasing (and still are, on a nostalgic level), but they're not an accurate depiction of what the pursuit of a 'connection' is in real life. Men and women dating online are persuaded - in some form or another - to get to know each other through strained personality profiles that, more often than not, are written to sell the idealized version of oneself. That pseudo persona that one creates is then prolonged and accentuated throughout the various dates - until one's true self inevitably comes out. When that happens, the superficial dynamic between the couple is exposed, and one realizes that there was never a strong base to work from in the first place.

In short, online dating spurs people to obscure the less personable qualities about themselves while heightening or embellishing character traits that they wish they had more of. While I'm glad that I persisted with this social 'experiment', I have now realized that some things are quite simply out of one's control. The best that we can do, then, is to open ourselves up to new experiences (and new people), and always keep your eyes peeled for that next special encounter.