057: 30 Times I Rationalized Staying on a Bad Date

In April 2019, I challenged myself to go on thirty dates in thirty days.

Every time I tell someone this, they’re appalled. Which is the only correct response, frankly. Thirty dates in thirty days is hell.

But I had an idea that this challenge would do a few good things for me:

• I’d see more of Los Angeles—I’d been living here for a little over a year at the time and had still only seen 4.8% of the city

  • If you get this very obscure The Good Place reference, we might be soulmates

• I’d meet new “types” of people. The last several relationships I’d had were uniformly terrible people, so I knew I needed to not go after my usual type. I thought this might shake me out of this habit.

• I’d feel less frustrated/intimidated by first dates in the future because, hey, at least I wasn’t going on thirty dates in thirty days again!

So I signed up for Hinge, put together a profile, and started swiping. At no point did I expect to actually meet someone this way.

And I didn’t!

Source.

I didn’t go on a second date with any of these people. I also didn’t see much more of the city because inevitably I ended up planning almost every date. So I just kept going to the same three bars or coffee shops because, well, I knew that the metered parking situation meant I always had an easy excuse to leave if I needed it.

(This is an excuse I still use today and you are welcome to steal it if you want something in your back pocket for your next first date.)

Here’s the thing about a challenge like this: Inevitably, you’re going out with people you wouldn’t normally because you have to meet your quota. (I tried to be upfront with folks about this without saying, “I’m going on this date to check a box.”) So I didn’t filter for anything that month. As long as I didn’t get a murdery vibe, I met them in person. This was part of the point (see above) but also had an unintended consequence: I got to meet people who I normally wouldn’t have a chance to interact with.

I met someone who had recently gotten out of jail for a drug-related crime. (End the War on Drugs, FFS.) I met someone who had ridden a motorcycle from Anchorage, Alaska to the tip of South America. (The photos were very cool.) I met someone who earnestly believes that lizard people live among us. (Why????) I met someone who had just moved to LA after working in a Vegas casino for ten years. (Asked him how many people he caught trying to cheat and he rolled his eyes.) I met an app developer who had never used a stove. (He went straight from his parent’s house to the frat house to a software company that serves three meals a day.) I met lots of well-meaning soft-spoken writers who I just didn’t click with. (Sorry.)

None of those dates turned into relationships, and I usually knew they wouldn’t in the first few minutes. (Chemistry—you either have it or you don’t.) But I never got up and left when I realized that.

There were natural ways to rationalize staying: I’d already ordered, I didn’t want to be rude, I could be wrong, et cetera. None of those were the reason though.

Recently, I was on a date with a neurologist. Twenty minutes in he asked me, “So why are you single?” Not in a cute, bantering way. It wasn’t, ‘you’re so great, how are you single?’ It was: ‘What’s wrong with you?’

The couple at the next table, who had been previously very engrossed in each other, turned and stared. I, stunned at being asked this, made up some nonsense about moving a lot. Then, suddenly getting annoyed, I asked him the same question, which he dodged.

At the next table, the woman caught my eye and emphatically shook her head. I already knew what she wasn’t saying out loud: Get out. I knew, but I stayed.

I stayed because after my annoyance faded what remained was curiosity. I had to know why this guy was like this. What had happened in his life that this was how he communicated with people? Who had taught him that being confrontational on a date would endear him to someone? Why was he like this?

People have asked me what it takes to be a good writer. I usually tell them I have no idea because I’m not a good writer, I’m a decent editor. But if they press for an answer I tell them this: Good writers—and probably great ones too—are curious. They’re curious about the couple at the table next to them, about why traffic jams knot up, about how a business was started. They know they may never get an answer but they start spinning out possibilities in their heads. Those questions lead to more questions and good writers let themselves fall down those rabbit holes of wondering.

Because a plot, when it’s first coming together, is just a rabbit hole. It’s putting a neurologist in a coffee shop and wondering, “Well what happens if this type of person sits across from him, or that type of person, or some other type of person…?” It’s saying, “I want this woman sitting by this disastrous date to intervene, but why would she? Because she’s been burned before? How, when, why?”

When a good writer does find an answer to their musings, they squirrel it away for later. They use what they learn about human motivation to make their characters seem more real. If I ever write a character who loves a conspiracy theory I know it’ll be because his life is unstable in some way, out of his control, and he’s scared about that. And it’ll ring true because that’s what I eventually realized was going on with Lizard People Guy. He needed the US to have an external enemy, a clear foe we could unite against, because otherwise the reality of American politics in 2019 was too scary for him. And why shouldn’t it have been? Between Trump and Russian interference and North Korean missile testing, there was—is—a lot to be afraid of. Who can say if his belief in the Lizard People is any better or worse than the people who just tune out or the people who become extremists?

I didn’t stay on any of these dates with the intention of becoming a better writer because of them. I stayed because I was curious—am curious to a fault. Even if I never saw them again, I couldn’t walk away without knowing how they ticked. It wasn’t malicious, it wasn’t to “collect” them in some way or check a box. I genuinely wanted to understand.

But seeing people and being open to understanding them, even when I profoundly disagreed with them, has helped me in my writing so much.

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