The First Time Asking Someone On a Date

And it goes terribly, horribly, soul-crushingly Not Very Well.

Photo by Jeswin Thomas on Unsplash

Dana DuBois had an interesting take on some data in a dating survey:

[embed]Only 1 in 5 Young Women Feel Comfortable Asking Someone Out. The coverage focused on dating. That’s not what stopped me cold.medium.com

Dana makes good points about how young people—and especially women, in this case—need to be able to make the ask. About whether they got the job. About getting the raise. About taking the next step in a relationship. And to Dana:

Asking someone out is, objectively, one of the lowest-stakes forms of interpersonal risk most people will ever face. The worst realistic outcome is that someone says no and you feel awkward for a week. Life continues. In the grand scheme of things you’ll survive, this barely registers.

Um, yes. Probably. For a lot of people. Probably for most normal people.

For weird kids, not so much. At least not one weird kid that I know of.

For some reason I still cannot explain, girls terrified me, starting in middle school. They still did in high school, but a lot of things terrified me in high school (I had been with the same kids from kindergarten through eighth grade, and bless ’em all, they never told me I was weird—the kids in high school were happy to make up for that lack). And then, in second semester English in 10th grade, I sat behind this girl who did this strange thing. Wendy turned around and talked to me. At the start of almost every class, before the bell. I cannot remember what started it, it somehow just became a routine. Never any deep discussions, and my contributions were mostly smiling and nodding and the occasional, “Uh-huh.” Every now and then I would make a joke or try a humorous comment. We never had any contact outside of English class.

After school I mowed neighbors’ grass. Pushing a lawnmower up one row and down the next gave me way too much time to think. Maybe… maybe… what if I asked her out? Like… on a date. (I had no clue what “a date” actually entailed. None of my small circle of all-male friends dated, that I knew of, and this was 1974, so the Internet as a knowledge resource was not even a concept.) But… maybe.

The school year ended in June. Wendy went her way, I went mine. Well. Okay then.

Push the mower down the row. Turn around. Push the mower back. Turn around. Repeat all summer.

Okay, look, there were about four thousand students in our high school, right? What are the odds that Wendy and I would end up in class together again? If we do, then it’s a sign! It means I’m meant to ask her out! So I came up with plans on the 4,000 to 1 chance that we’d be in class together again.

Side note: I took probability and statistics in college. Allowing for grades, ability groupings, and class sizes, the odds were actually better than 3 to 1.

First day of 11th grade. First day of English class. Different classroom, but I sat in about the same desk I had been in the semester before. Wendy came in, sat down in front of me, turned around and started talking, filling me in on her summer.

The universe had spoken. We were meant to go on a date. So I asked her out right then.

HA HA HA HA HA no.

School started early September. It was not until the leaves were in full color, so maybe early- to mid-October, before I actually got up the nerve and asked Wendy on a date. On the date. Sit down, take deep breaths, stay calm, look confident.

Wendy sat down and started to talk. I waited until she paused and asked her out.

She looked at me.

Her expression got strange.

She burst out laughing.

I gathered my books, stood up, walked to an empty desk by the windows, sat down, and looked out at the trees. (This is how I remember the leaves in full color. Very strong memory for some reason.) I got through the rest of the day. And the week. And the…

I dunno, that semester has a lot of blank spots. I was sure that Wendy would realize that she had been cruel, and would come to me and apologize. I sat in the desk by the window from then on, where I knew she could see me when she came into English. She would see me, and come over and apologize. Maybe this class.

Maybe next class.

Or not.

My academics suffered. I got a C in algebra that semester. I had never gotten a C in anything before. My last three semesters were better, academically, but I graduated number eleven out of 919 students in my class. The top ten students in a class get special recognition at graduation. My father, who had put up with a nebbishy son with no athletic talent, no looks, no social life worth mentioning (from his point of view), had at least consoled himself that nerd boy would get some academic achievement awards. Know what graduate number eleven gets? A diploma. Like everybody else. My father made me go to the awards presentation so I could watch my ten better classmates get recognized.

In college, there was a woman who sat next to me in calculus class, freshman year. We talked to each other, and walked to and from class fairly often. I thought she must like me.

So what had I learned from my previous catastrophe? Well, when I asked her out (to a student play), I did it via campus email. That way I wouldn’t have to watch her when she laughed at me.

She replied in the affirmative. Kinda. It was not a date, it was just two friends going to an event together, she explained in the reply. And explained again when we talked about it later. And again on the night we went to the play, on the way to the theatre and the way back to the dorm. Where she said, “Thanks! Good night!” and went to her room, and I went to mine.

I did go on one actual date in college, almost two years later. It went badly, in the sense that Titanic’s maiden voyage could have gone a little better than it did. But at least on my date, nobody died.

By 1987 I still had never told anyone about the Wendy fiasco. But for whatever reason, that year I told my best friend and lesbian buddy, who was nicely sympathetic, even as I was on the edge of having an anxiety episode just preparing myself to talk about it, over a decade later.

Twelve years, a marriage, and a divorce later, I decided to tell my new best friend and heterosexual buddy (now my wife) about the Wendy fiasco. Deep breaths, stay calm, okay, now remember Wendy’s face as she started to laugh—

Wait. Back up the tape.

The look on her face. Wendy’s confused. Very confused. Why would—

Oh my gawd oh my gawd oh my gawd she thought I was making a joke! She never got my jokes. She could never figure out my sense of humor. She would try, but most of the time she would just laugh without understanding what she was laughing at.

So. It took twenty-five years, but I finally got it. I was just some guy with a weird sense of humor who sat behind her and was easy to talk to.

I had received multiple compliments from women friends over the years that I was easy to talk to, and a good listener. Never made the connection. Dates (or even just friendships) with women who didn’t get my sense of humor never went well; both my ex-wife and current wife not only get my humor, they bounce it back to me with a wicked spin.

But my point, Dana (and anybody else still reading) is that in the grand scheme of things, sometimes asking someone out can be a tad traumatic.

That does not mean you shouldn’t go for it, however. Because I bet the worst that could happen to you won’t beat my worst case. “Hey, there’s this guy online, and you won’t believe what he went through…”