Анжела was a self-proclaimed "Wisconsin girl."  Also a research scientist working in a university lab.  Tough-minded, very friendly, with a positive attitude and a very natural mode of dress and comportment.  All things that I liked, on paper.

There was something that I found immediately strange though. All her correspondence was in short stanzas with no capitalization and almost no punctuation, as though her inner monologue was free-form poetry. We sent a dozen long messages back and forth before we arranged a date, and she never strayed from her pattern.

Her opening message to me was:

your words make me think

you are an elitist

in many respects.

i prefer to delude myself into thinking

that i am not

which then makes me one

doesn't it?

At this time, a meme was drifting around in the still-developing world of online dating, about something called "negging." Doing this meant starting a first conversation by making a negative observation about the other person, forcing them into a subordinate position of power, where they feel compelled to defend or justify themselves to you. It was supposedly something that pick-up artists did, to try and get women in bed as fast as possible at the expense of their self-esteem. I'd heard of it, but I had no idea if it was a real thing, statistically. I wondered if Анжела knew she'd started in that territory. She was probably just trying to be funny.

Scientist that she was, Анжела declared that her presence on okCupid was an experiment she was conducting to see how she reacted to online dating. She didn't seem to be applying a lot of rigor, though. She rescheduled our first date a few times, then said she needed to potentially cancel any time up to the night before, which informed me that she was probably cramming me in around too many dates with other men that she was negotiating with all at once.

...No, I don't think I was jumping to that conclusion unfairly. Even the busiest woman I'd ever dated - Кэрол - was able to make a single declaration for a time and a place to have a first date, and stick to it with confidence, even though she was in a high-stakes management job and also juggling back-to-back dates with me and another man. First dates are important, and if you're throwing it all over the place on the calendar, while logging into okCupid every day, you're either fatally disorganized, or deliberately bringing your C-minus game.

That's one of the most horrible things about the accessibility of dating apps: People who are taking it seriously are mixed randomly together with people who are not serious at all, or even malicious. It's a jungle in there.

I arrived up at her place a few minutes late and all sweaty from a bike ride, after having some difficulty finding her house. It wasn't a very good showing on my part, but she seemed to take it in stride. I confessed that I felt too gross to be acceptable in a fancy restaurant. She very kindly loaned me two of her shirts and waited while I took a bird-bath in her sink.  There was no sign of "negging" or anything close to it: From the first moment in person we dropped into a lovely banter, with plenty of jokes and side-references. She ranged around the conversation effortlessly, and slid into a nice partner context as she drove to the restaurant and I read out navigation on the phone. The only wrinkle was that I felt a little nervous keeping up with her, as though her high energy level demanded that people around her speed up to match it.

After storming through a variety of topics, we decided to share a few stories from our dating past, while acknowledging that it was a tricky subject because it could easily bleed into the present. I chose the tale of my recent history with polyamory, because I thought the car-crash nature of it might be something we could laugh over, but while I was giving her the basic outline I saw her expression change. The smile faded from her face, and all her energy seemed to drain away, turning her into a different person.

I edited the story down to just a few sentences to kick it behind us, sensing it wasn't a good topic. Instead of commenting on it, she began to tell me her own story, with an equivalent car-crash nature: She'd been deeply in love with a guy that she'd had a long-distance relationship with, and then he'd suddenly cheated on her, breaking her heart, and damaging her severely. He'd been very callous in the aftermath, and it had taken her years to recover, and made her weirdly paranoid in several relationships in the meantime, to the point where they too were derailed.

She was on the edge of tears as the finished the story, and it was clear she was still not finished rebuilding herself from it.  I knew that was a red flag, but I decided that from my point of view, Анжела was still a fine person to date and even a good person to consider a relationship with because it seemed to me she had the tools to keep working on her trauma and plenty of space to exist outside it. I couldn't blurt something like that out at the dinner table of course - it would be weird and judgmental - but the thought did form in my head. In the immediate moment I just wanted her to feel better, and get back to having a nice evening.

The trouble was, I couldn't find a way to rescue the mood. I offered kind words and apologized for reminding her of the incident, and I didn't know what else to say. More stories about trauma seemed inappropriate. I had a story from my own past about being cheated on, but telling that felt wrong. Eventually I changed the subject and things brightened up, but not to the happy, effervescent state they'd been before.

After dinner we drove back to her house, and she said she'd had a nice time and wished me well as I rode my bike away, but I could tell something had gone sideways.

I sent her a thoughtful summary of the evening, saying how much I appreciated her conversation and helpfulness, and the ease with which we collaborated, and saying I was open to another date any time. I did confess that I felt a little nervous tension at the end, and suggested we do something relaxing next time. She responded with a few stanzas:

thank you for your assessment of the evening.

I do not know you well enough

to like or dislike you

but we have interacted sufficiently

for me to determine that the tenseness

would not easily subside.

good luck in your quest.

I was upset. Arriving sweaty and invoking trauma had not been good moves, but I still felt like I'd been rejected unfairly. There was nothing I could do of course. I decided to ask for an explanation, though I knew I didn't deserve one:

Out of curiosity - not out of a desire to argue the point - what “went wrong”?

The response was one line:

what “went right”?


That shut me right down.

My ego was bruised. I began to feel sick with dating, and wrote a frustrated journal entry on okCupid about how everyone seemed to want fireworks and chemistry on the first date, or was shopping for something without factoring in the basic humanity of themselves or their potential partners. It was pretty shrill, but I got a few people commenting kindly on it anyway.

Weeks later, Анжела would spot me at the Museum of Modern Art, on a date with an extremely attractive young lady named Авра.  I was nicely groomed and dressed in fine black clothing for the fancy event, and feeling quite confident, and she stared me up and down with a curious expression that I couldn't read. Was it interest, or panic?  At the time, I didn't even recognize her. All I remembered was feeling confused to see some vaguely familiar woman staring bug eyed at me, then I caught up with Авра and moved on to the next room. I only realized it was her from a casual-sounding message she sent me later on.

I saw you at the museum of art last weekend.

tell me how you have been.

I ignored it. I felt there was some kind of danger in reconnecting with Анжела, because the way she came across in text was so strangely different from the kind way she acted in person. Which side or her was real?

The whole incident also gave me food for thought about second chances in the online dating world. When you're offline, out in public, there is no expectation that a date is going to happen. You either keep showing interest or you don't, and if you don't, it was never a date: It was just some casual conversation in a store, or some friendly comment on public transit, or whatever. But online, as soon as you agree to meet in person, it's a date, and that means there are stakes. Now you suddenly need to keep from blowing it. You have time beforehand to worry about how you look, what you say, where you go, et cetera.

This all seems to point in one direction: No one should ever get a second chance in online dating, because if they blew the first one they clearly didn't deserve even that.

But of course, there's also zero guarantee that the person you're about to see is anything like the person you're picturing in your head, or the person who appears on your phone. This means a first date is much more likely to have a bad outcome, statistically, than one arranged in the real world. So you end up preparing for a crappy date just as much as you would for a great one. That's potentially a lot of wasted time.

It can get overwhelming. You might be tempted to show up in rumpled clothes, under-slept, ten minutes late... Book two dates a night, five days in a row, cancel them or just fail to show up... Put the onus entirely on them to impress you, and if they don't, ditch them in the middle of the meal... What are they going to do, send you a snippy note and get blocked? If most of these people are going to be rejects, why spend the energy, right?

Mulling this over, I looked at the last six months of dating and realized that I was guilty of this lazy approach. It was to a lesser degree: I'd never stood anyone up, or failed to do any preparation, and I'd certainly never tried to be callous, but I did feel like I was in some kind of hurry, which was ironically causing me to waste time overall. Like, instead of arriving sweaty at Анжела's house, I could have left earlier and finished the last few hours of my workday at some cafe a few blocks down, then walked over, just to make sure I didn't have to rush.

How could I bring my A-game if I was in such a hurry? How could I pay proper attention to anyone when other personal things - like my work or travel schedule - devoured all my time? I was placing romance at the bottom of the priority scale, cramming it in between shopping trips and grafting it onto my dinners. What was the point? Just the distraction?