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Jane Dates: The very first time

Our first guest post in the Jane Dates column on online dating: the very first time.


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This is a guest post for our Jane Dates column, from another online dating veteran. To submit your own online dating story for consideration, email

After ending a relationship almost exactly 7 years after it began, I was kind of hoping that a magical Vacancy! sign would light up in neon above my head so that eligible bachelors could just sign in for me to choose from. (Whoa, not a metaphor for how I actually operate… yet.)
Enter OkCupid, today’s version of the next best thing. It all looked so easy. I get to write what I’m all about, toss up a few flattering photos, and start basically online shopping for men. What could go wrong?

So I hopped onto the site, populated my profile with interesting factoids, witty observations about life, and fascinating trivia. Before I even hit save, guys were winking and viewing and flexing their biceps at me. Ah, singledom. High on attention and romanticized possibilities, I started reading incoming messages:

“Nice legs gorges, lez meet up.” Umm, block? Next!

“Hey you asian honey I wanna kiss and lick ur…” BLOCK! Next!

“Hi there! You have a really nice smile.  :)”

Before I have even seen this message sender’s profile, I melt—because, well, he just sounded so normal in comparison.

I clicked into his profile and drank in his tatted-up arms, low-key hipster vibe, and alt rocker persona. “I play bass,” I read, imagining his nonchalant shrug. Nothing like a bad boy rock star to help me get my groove back.

I clicked back to his message and responded enthusiastically, thoughtfully referencing key points from his “Six things I could never do without” (music, sushi, chocolate…) and “What I’m doing with my life” (playing bass for his band, settling into a new city) sections.

In fact, I wrote volumes to him. Things about how I love the things that he listed, and what I’ve done that proves it, and how it’s super cool he’s in a band. I hit send. And waited.


And then a full 20 minutes went by—an eternity, in other words. At minute 19, oh relief! Hipster Rocker’s response hit my inbox right before I completed the text. And miracle of miracles, he also wrote volumes. He was amazed that he had found someone else who also loves music and sushi and chocolate! What are the chances!

That was the beginning of OKCupid virtual romance #1. Over the span of two months, I rushed home from work, logged in, and devoured his nightly missives before gushing forth my own. We talked about everything, this long distance Romeo and I: the specific ways we like to eat the food we like to eat, separating one type from another on the plate and planning our last bites of each meal. How the weather was that day and how we dressed for it, dealing with the exigencies of office climate and commuter variants. 

After two lovestruck months, and sharing mountains and mountains of said personal eccentricities and meaningful details, we tiptoed toward the inevitable next step—to meet in person, certain that we had discovered the happy ending to our respective rom-com lives. 

The big meet up was arranged for coffee at a quiet cafe a Monday evening. And from the start, it had none of the gushing personal sharing of our online exchanges. In fact, the silence was deafening. The only customers in the place, we were outnumbered by the yawning staff—which embarrassingly only accentuated our profound inability to speak to each other. The words that had flowed forth from our keyboards so easily stuck in our throats. I swallowed my cappuccino audibly. He did the same. At least we’re still in sync at swallowing, I thought.

Not speaking at least gave me time to study Hipster Rocker. It looked like he’d given up on eating since his profile picture was taken, because his face was gaunt, with hollows for cheeks. The sinewy tattooed arms that initially made me swoon were revealed as, well, scrawny. Hmm, maybe that’s why he wanted to talk about food so much.

I tried to think of something to say. Oh yes! Our love of sushi! The love that brought us together.

“Have you had any good sushi in the city yet?”

“It’s too expensive,” he replied tersely.

Umm. Ok, I could relate, but he wasn’t really the wordsmith I’d fallen for online.

We stood up to leave, gulping our coffees quickly, glancing miserably at each other over the rims of our cups. When the check arrived, he began counting out coins for the exact amount of his share. The waitress stared and threw me an awkward, sympathetic glance. At this point, I was desperate enough to throw money at the situation just to get out of there. Forget the coins, here’s five bucks, let’s leave.

Outside the cafe, perhaps encouraged by my five-dollar generosity, Hipster asked me to dinner. Before I could register that the animal part of my brain was screaming, FLIGHT! I said yes. Why, you might ask? Well, back then, in the early days, the hopeful days, the naive days, I was still optimistic about every possibility. Maybe we were just in a rough patch and could still emerge from this as soulmates! Because, you know, we like to eat food the same way!

Hipster and I began walking around in the cold, searching for a suitable restaurant and watching little puffs of steam float up from our breaths. He started to tell me about his ex; how much they used to talk, how our messages had made him feel like he had that again. I nodded, feeling sad for him and for myself. My brain squirmed into the back half of my head to settle in and disinterestedly watch the rest of the night like a bad B-movie. My brain is a jerk.

We settled into a tiny Italian restaurant which was decorated with charmingly unironic red and white checked tablecloths, tiny bud vases filled with fake dusty flowers, and wood paneling on the walls. Maybe it’s our Lady and the Tramp scene! my brain perked up and cheered, when we both ordered spaghetti and meatballs, glancing at each other and grinning over the coincidence. This might get better!

He studied my face as the waitress left, and suddenly I felt calm and happy. Here we are, and this is a nice moment, I thought. Right before this: “My ex is also Asian, and she was very hot.”

I blinked. Did that really just happen? Unfortunately, he took this as a signal to continue talking, and then began with a highly detailed blow-by-blow of this last relationship. My brain sneered, Nope, we knew it and began to eat popcorn noisily while watching this horror unfold in the abandoned sticky-floored theater of my life.

I went into survival mode: tucked my head down and shoveled giant forkfuls of pasta into my mouth to make the meal go faster, and to make it impossible for me to speak. There were bits of meatball and sauce spraying everywhere. I noticed a glob land on his head and neatly tuck itself into his hair, but even then couldn’t look directly at him. I was on a mission to escape.

This is when Hipster crowed, “I think we’ll share a dessert!” And welcome back, dear readers, to the particularly circle of hell that is a never-ending OKCupid date. I know you’ve all been here too.

I slumped in defeat and shoved the plate towards the waitress as we asked for the check. Once again, I wanted to throw as much money on the table as it took to get me out of there. Just tell me how much to expunge this dating disaster forever.

I know all you online daters out there have a story just like this one. And what happens to us afterwards, once our hopes and optimism is crushed, once we’re confronted with the awkward coin counting, the detailed breakup recounting, the painful silences? Because it ruins everything that comes before it, all the possibility you dreamed up and enjoyed in the rush of those first exchanges, all the hope that this is finally your rom-com movie scene, completely with music, sushi and chocolate. The truth is, I wish we’d never met. If I could go back, an older and more experienced OKCupid dater, wise to their ways, I’d have wrung a few more weeks or even months out of our online correspondence.

Because that was the good stuff, as it so often is. It gave me something to look forward to back then. A virtual boyfriend who wanted to hold me and hear what I had to say. And maybe that’s worth something in and of itself.

Sometimes reality just messes romance up.

Photo by apparena/Flickr

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