Never Sext a Stranger

And, other lessons in online dating

Image by StockSnap from Pixabay

I sucked at online dating. Correct that, I sucked at dating. Period. Being a boyfriend was easy. Romantic dates? Check. Remembering special occasions? check. Surprises and fun getaways? Check and check, several times a year. But, leading up to all of that? You got me there. For someone who thought they had a way with words, my approach was lacking, and online dating only made it worse.

It was 2014 and Tinder found its way onto the phone of every millennial. I figured it would be easy; they literally built a cheat code. No more hitting bars every weekend (and some weeknights). Women could magically appear on the screen. Plus, all I needed to do was swipe until something stuck? Minimal effort and maximum reward. I thought it would be great, but then my real stats came in. Have you ever played, what you thought was, the best game of your life, only to realize that you barely contributed to the box score? It was like that, but with alcohol. Three months of swiping amounted to a bunch of meaningless conversations, a few awkward moments, and one date that I’ll never forget.

Let’s start with the awkward.

Fun fact: when you get blocked on Tinder, the entire conversation is deleted. I didn’t know that, nor did I ever think that I’d be the creepy guy to get blocked, yet here we are.

I matched with, who I thought was a prime candidate: a teacher born, raised, and working in Brooklyn, around the same age, went to Penn, and was considering going to law school. Ambitious, cares about her community, and Black. Check, check, bonus.

I came across my ex-girlfriend’s profile during the same week. For context, we were close friends, exchanged dating stories, and once I turned to Tinder, I helped her set up her profile, as well. So, when her picture came up, I jokingly swiped right, and she did the same. When we matched, we used the app to do the same things that we did via text; make jokes, share stories, and make plans for the next time we were going to hang out. For additional context, for us, inappropriate jokes were prerequisites to any meaningful conversations, so when I mistakenly texted the teacher with a message meant for my ex, that was a problem.

I was returning a car rental, when the teacher sent me a message. I was simultaneously texting my ex when I asked, “What dat mouf do?”

Let that marinate…

I texted a complete stranger the most awkward and cringe-worthy and sext and it wasn’t even the least bit smooth.

I realized my mistake the moment that I hit send and immediately regretted it. You know how Instagram lets you delete a message before someone sees it? Well, this wasn‘t Instagram. I tried to explain, but what could I say?

Sorry, that was for my ex?

JK, so how about lunch?

Oh, no what I mean is, do you enjoy public speaking?

I couldn’t think fast enough and she was gone before I could finish “sorry.” Like I said, awkward.

No worries though, swiping was life and I was starting to get the hang of it.

She’s funny. Right.

Seems smart. Right.

Loves cats. Left.

It became pretty routine.

Then there was the date; not the worst in the pantheon of dating stories, but it definitely made me rethink this online thing. The willing participant was a twenty-something-year-old Latina journalism grad student at Columbia. We hit it off, and after two days of texting, we agreed to meet up for drinks in Harlem. She chose a spot not too far from her place — one that she’s been to before. I worked downtown, so I agreed to head up there when I got off. I was excited. She seemed cool, attractive, and definitely not crazy. Plus, I didn’t accidentally sext her, so things should’ve been simple when we met in person. Right?

Not at all.

I was running a little late and made the first of a few pivotal mistakes. I opted for a cab during rush hour. A dumb move, but in my defense, the train was delayed, and also, I was pretty dumb. I sent a text to apologize and she quickly replied, “No problem. Did you change the reservation?”

A reservation? For drinks? Did I mention that it was Wednesday?

Confused and not wanting to come off as rude through a text, I quickly replied, “No, didn’t think that we needed to.”

“Oh, I thought that you would. It’s fine. I’ll check out the place next door.”

We ran into some traffic, so I had some time to check our previous messages. Did we talk about reservations? Didn’t she recommend this place and invite me? Can’t she make a reservation? What happened to equality? I read all of our messages and there wasn’t a single mention of needing to call ahead. I brushed it off and besides, I was only five minutes late. It should have been fine.

I hopped out of the cab and couldn’t resist peering through the window of the first place. Tables — empty. Bar stools — crickets there too. Again, it was a Wednesday at seven. We could have easily met up there, but she insisted that we try the place down the block because, again, I didn’t make a reservation. The other place was empty too, so it was easy to spot her. Curly hair tied back, and a white blazer.

“Hey, are you Stephanie?”

“Yeah, Jayson?”

I sat down and could tell that something was off. She wasn’t very warm, didn’t make eye contact, and wasn’t saying much. Maybe, I wasn’t what she expected or she needed a drink to loosen up. I was nervous too, but the hard part was over, I’d much rather talk face-to-face than send emojis.

We settled on the basics: career, school, and life goals. She was in her first year of journalism school and loved going into the field and capturing stories. I told her about my ties to the New York Times through their scholarship program, and the summer I wrote political blogs for their website, during the Obama campaign. Then I messed up.

“What do you think about the decline of paper news and the transition to online platforms? It’s crazy that the Times recently put ads on their front page.”

Her eyes widened. They were green with brown flecks. I hadn’t noticed. She leaned back in her chair and stared off for a few seconds. It was a loud bar and the liquor was kicking in. I thought I’d repeat myself to make sure that she heard me and then it came.

“The news industry is fine and for you to say that shows that you know nothing about journalism!”

Now my eyes widened. They’re just brown.

“I didn’t mean to offend you. I’ve just been reading up about it. I actually spoke to one of my mentors about it.”

“Well, your mentor doesn’t know much about journalism either,” she replied, as I watched some spittle escape her mouth and land on my lip. Tequila…great.

“She’s a journalist,” was all I could get out.

We sat there for a moment, sipping our drinks and stealing glances at the TV.

“What do you make of your line of work? Is it hard?

Finally, a segue.

“Social work? I mean, yeah it’s challenging, but I really want to help people, so I’m happy with it.”

I was happy about the change of subject. Clearly her career was a hot-button issue.

“Right, but how do you feel about taking people’s kids away?”

I took a sip of my whiskey. A long sip.

“That’s not what I do. Most social workers don’t do that, actually.”

It would have made sense if the date ended soon after that, but it didn’t. We had a few more drinks and then I walked her home. Her place was only ten minutes away, but the awkward silence made it feel longer. It was next-level, day after the apocalypse kind of quiet. Think Will Smith in I am Legend, but with no zombies.

When we got to her building, I wasn’t expecting much, but we hugged and even said “we should do this again.”

Of course, we never did.

I kept at it for a few more weeks but swiping lost its appeal. I deleted the app and decided that if we didn’t first meet in person, then we wouldn’t meet at all. I wasn’t any good via text and it turns out that I didn’t need to be. That ex who I meant to sext — we got married.

Like I said, I suck at online dating and I’m never going back.

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