An Assortment of Adventures in Online Dating

We walked down Ashland Avenue toward my apartment, breaking from laughter only to suffer through awkward pauses. She was a 20-year-old, 5-foot-nothing former swimmer who seemed to glide effortlessly between ease and discomfort. I was a 23-year-old awkward man who had the dating experience of a 16 year old. We were half-drunk, the night was cool but the air was humid and I was going to invite her inside for a night cap.

Butterflies fluttered in my stomach. “Would you like to come in?” I practiced inside my head. “Welp, this is my street. Wanna uh…” “Do I really talk like this even in my own internal monologue? Jesus, man.”

We got close to my apartment, passing by a McDonald’s, each looking at different landmarks and then back at each other, smiling and looking away again. Our conversation lulled, but I wasn’t concerned. After all, we had just spent an evening together drinking beer and watching comedy – lulls are normal.

And at that moment, she stopped, turned, and threw herself into a cab.

The cab sped away. I spun like a top as my body turned from watching her dive into a cab to watching the car disappear south down Ashland.

My face burned with embarrassment. Wow, I thought, I guess that wasn’t just some lull. She wasn’t having a good time? What did I do? I was sad and furious and confused and slightly amused by the Vaudevillian cab dive; it almost looked as though she was kidnapping herself, I thought, tossing herself into the car by the collar of her shirt. But fury and confusion beat laughter: If she didn’t like me, why didn’t she just tell me, then leave? Why embarrass me?

I mashed the buttons of my phone, texting her: “What the hell was that? You could have told me if you were having such a bad time.”

I slunk home, not expecting her to respond. There’d be no one joining me in my apartment tonight, I thought, sighing to myself. The stomach butterflies metamorphosed into stomach acid as I stewed in the pain of rejection. I poured myself a glass of water and sat by the window, my pounding heart providing a steady beat to my confusion. I replayed the night in my mind: We drank beer at my apartment. We went to a comedy show. We walked down Ashland, then she flew into a cab, the cab flew away. At points, our conversation was staccato and awkward, but it was rather nice, perhaps a bit benign, at other points. Was that the problem? Am I boring? Too nice? Am I so nice and so boring that people want to fly away from me and hurl themselves into cabs?

The phone buzzed. It was her: “Oh my god I’m so sorry. I literally peed my pants. I’ve never felt so embarrassed in my life.”

I stared at the text and grimaced. If this was a lie, it was a bizarrely self-effacing way to save face. If it was the truth, it was a strange – if not vaguely understandable – way to react to pissing your pants. I thought of myself in her shoes: what if I was walking down Ashland Avenue on a second date and I had pissed my pants? I felt my cheeks glow red. I felt sorry for her.

“You could have borrowed some basketball shorts!” I wrote back to her, trying to show her that I get it: piss happens. “Pee isn’t a big deal.”

She never responded.

Later that night, I called my friend Virak and recounted my evening. He laughed as I told the story. When I finished, I heard him breathe deeply, exhale, and say “Well……. looks like you’ll have to let this one soak in.”


She was into religion and serial killers, she told me. I asked about a sect I knew: No, not that kind of religion. Or that one either. Which ones? Eh, I don’t want to talk about it, she said. OK. So, why do you like serial killers so much? I don’t know, she said, there’s just something about them. Her lips curled into a love-sick smile and she sighed a bit, rolling her beer glass between her palms. They’re so interesting, she said, so human. I taught her how to play backgammon; she quit halfway through the game. I hate this game, she said. Alright, we can just talk, I said. So, what do you think about the Catholic Church? I told you, she said, I don’t care about that kind of religion.


Her: Hey, are you busy?

Me: Hi! No, I’m not. How are you?

Her: I’m good! Listen, I wanted to talk to you. I had fun the other night and you seem like a good guy, but I didn’t want to just leave you hanging with a vague rejection like I did.

Me: Oh? What do you mean?

Her: Well, I wanted to tell you that the reason I don’t want to go out with you again is that I’m not sexually attracted to you. But you seem like a nice guy.

Me: …..OK. Glad to know, I guess.

Her: I just didn’t want you to think it was something else you had done.


“Are you close?” she asked me as we both had a bad time.


I was disappointed at her real-life appearance compared with her in-photo appearance. She had been careful to post flattering pictures of herself online, I saw. Although she didn’t look awful – more plump, dead-eyed, jagged-mouthed than she let on in photos, but she wasn’t grotesque – her lies turned me off. I felt duped.

(This could describe any number of online dates, where “I look like Kim Kardashian” under “about me” is long-hand for “I have a huge ass, and it’s not necessarily under my control” and where “By the way, one of my eyes is sorta googly and out of place at all times, something that I’m still uncomfortable about but willing to surprise you with” is implied – or not – instead of written. Online dating is shallow, but it’s also a terrible combination of duplicitousness and self-consciousness. And yes, that includes the extra inch or two I gave myself under “height” for years and the friendly angles I gave my own pictures to hide my bulging belly. I’ve lied too.)

We sat at Fat Cat, a bar on Broadway Avenue in Uptown. I had ordered a beer while I waited for her to arrive, so she walked to the bar to order her own drink. As she turned her back, I gulped half of my beer – I knew I’d end this date early.

She returned from the bar and said, sans any facial expression: “So, I hope this is OK with you, but I can’t give blowjobs. My jaw is too tight, so it just doesn’t work. It’s too painful for me.”

I hadn’t planned on asking her for sex, nor did her profile mention sex or blowjobs or tight jaws, so I was a bit taken aback. I tried to be honest: “I don’t know what to say to that.”

“It’s cool, I mean, guys usually don’t mind because of my huge tits,” she said.


I changed the subject. What beer did you get? Where are you from? Something pointless, something far away from pained jaws to get her talk so I could drink the rest of my beer. Moments of conversation passed, perhaps five. A swig remained, particles and bubbles floating in the finger of red-orange liquid.

“Do you like me?” she asked, looking me in the eye and holding the stare.

I felt myself wince. “To be honest, no, I don’t think this will work out. I’m going to finish this beer and leave. It was nice to meet you, though.”

“Wait, I mean..why? Is it about how I look? Am I not what you expected?” She remained calm and kept the same placid look as when she discussed her over-tight jaw.

“Well, you must admit you don’t look like your pictures.”

“I’ve heard that before,” she said, slightly sighing, then smiling. “Hm. Do you want to come to my place and fuck me?”

“What? No, no thanks. I can walk you home, though.”

So I did, batting away come-ons, each a bit less sexual and a bit more friendly. My “no thanks” had been accepted; I was a friend now. She hugged me before walking to the door, waving, and closing the door. I shuddered. My jaw tightened.

I walked home feeling confused, as I often do after online dates, and deleted my account. Two weeks later, I created a new one.

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