This Month-Long Dating Experiment Did Not Go Well

Photographed by Alice Gao.
My father has a funny platitude he likes to use whenever I bring up my dating life. "You may not have hit anything out of the park yet," he'll quip. "But you're getting a lot of at-bats." I, like many young women in New York City, consider dating a numbers game. As a heterosexual, cisgender female, I talk to many guys in real life and on a handful of apps. I set dates with a small pool of them, and actually meet face-to-face with an even smaller number. There are always flaky dudes. This is part of the game.

Men will flake for myriad reasons — they get busy with work or they're sick, or they'll just flat-out not answer your texts like they have no home training whatsoever. I've been dating for so long and this has happened to me so many times that, at some point, I stopped letting it bother me. When friends would complain about guys ghosting, I'd shush them and point them in the direction of the hottie bartender at the pub we were at.

But one day, after having a hot Australian dude flake on me the day of the date, I said something to my beauty director, Cat. "I was really looking forward to sitting across from his beautiful face and hearing him talk about Foster's," I said. And she came up with a wild suggestion. What if, she asked, I sent all my potential dates Google Calendar invites when setting our dates? Would it make them more or less likely to stick to the plan?

I know how crazy this sounds, trust me. We live in a society where single women want to be seen as "chill" more than anything else. We never want to seem overeager or clingy — and is there anything more clingy than sending a calendar invite to guarantee you sure as shit don't flake? It goes against everything we're taught — like, that we're supposed to act completely nonplussed if a man doesn't answer us. (God forbid we get pissed off. That would be "crazy.")

So, I decided to wade into the "crazy" waters. For a month, I'd send half the guys who asked me out Google Calendar invites for our dates (from here on out, I'll call them GC guys), and with the other half, I'd refrain. Maybe I was naive, but I really didn't expect anything major to get sussed out. I figured I'd get the same number of flakes on either side, and that some men would actually see the calendar invites as a positive thing. Who doesn't need a subtle reminder?

Well, my friends, I wish I could say things turned out well for me. But, during the whole three weeks of this experiment, I did not actually go on one single date with a GC guy.

Here's how it would typically go: I'd match with a guy, we'd get to chatting, and one of us would suggest a date. We'd pick a date, time, and a place. Then, I'd say something along the lines of, "Do you have a Gmail account?" (Luckily, all the men I asked out were on Gmail. I don't fuck with Yahoo users.) Some would offer up their emails immediately, while others would want to know why I was asking. "Oh, I'm just going to put it in my calendar and I'll send you the invite." Radio silence. One guy told me that was totally creepy, and then stopped answering my messages.

Most of the men who gave me their email addresses would ignore the invites I sent them. Two of them flat-out declined. I was completely floored. I had never been so routinely dissed by random men on the internet, and I went on two first dates a week last year. Were men really and truly that turned off by an assertive woman?

I brought this up on a date with a non-GC guy during the experiment. "I'm doing this thing for work where I try to get men to not flake on dates by sending them Google Calendar invites," I explained to him. He almost spit his beer out in laughter. "Have you gotten a single date?" he asked. When I told him no, he explained that sending a calendar invite was almost as bad as finding and adding someone on social media without having met them in person. "It comes off as overeager," he explained.

I was pretty much disgusted by all of this. But then I turned the question around on myself: Would I be weirded out if a guy sent me a calendar invite ahead of a date? I truly didn't know. So, I did the next best thing. I polled friends — straight and gay. The response was pretty much unanimous: They'd be weirded out, and for the same reason the guy I went out with said. The whole thing reeks of desperation.

So, that leads me to a question I'm still grappling with: Why are we all so desperate to seem not desperate? And further: What the hell is it about a calendar invite that reads as desperate?

I maintain that it's what Amelia Diamond of Man Repeller describes as "The Big Chill." We've gotten to the point in which we don't want to commit to anything, show extreme interest in anything, or proclaim to be excited about anything. When it comes to relationships, we'd much rather be chill. We don't want to rock the boat. We want to keep things casual. We don't want to be responsible for other people's feelings or time. We want you to feel like we have so much going on, that, if you do happen to flake, we have another six dates waiting in the wings.

But, if you really think about this, most of us don't actually feel like this. We're probably disappointed when someone flakes. And, most likely, we prefer to have concrete plans over fluid ones. To me, sending a Google Calendar invite is the same thing as being clear about your expectations. It's saying, "I'm a person with valuable time, and so are you. Why don't we respect that in one another?" I think it's time we start prioritizing that over feeling "chill."

So, to the next guy who decides he wants to ask me out, please feel free to send me a Google Calendar invite. All that will say to me is that you're interested in keeping a date. The rest we can figure out over martinis.

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