You Could, I Dunno, Like, Ask a Question.
America, what did you do to your little boys to make them grow up to be the worst conversationalists on Earth?
I’ve pretty much been out of the dating pool since 2019 when I went into filming my show then started dating Joey. Joey and I broke up May 2022, then started hanging out again, then fully ended things again just recently. It’s been a confusing run and we care about each other but ultimately you can’t make something that doesn’t work work. So I’m venturing back out into the terrifying world of dating and apps and remembering just how tricky that is in a city like Los Angeles.
Here’s my main issue. Most men are seemingly fucking terrible at having a conversation. Now, just so we’re on the same page from the get-go, let me mansplain to you how a conversation works.
INSTRUCTIONS ON HOW TO HAVE A CONVERSATION:
I ask you a question.
You respond, then ask me a question.
I respond, then ask you a question.
You respond, then ask me a question.
And so on and so on until we die.
INSTRUCTIONS ON HOW NOT TO HAVE A CONVERSATION:
Here’s how 99.99% percent of the conversations I have on dating apps and on actual dates go:
I ask you a question.
You respond.
I ask you a question.
You respond.
I ask you a question.
You respond.
And so on and so on until I die of old age, my withering boney skeleton fingers reaching desperately for the nearest exit, trying to get as far away from you as humanly possible.
That is not a conversation. That is Fresh Air with Terry Gross except I’m Terry and you’re Gross. Ask a question.
Ask a question.
It probably will not surprise you that I am actually a pretty good conversationalist. A long time ago I realized most people just want you to hear and validate them. We’re all basically narcissists that love the sound of our own voices and that’s something you can use to your advantage. So if you’re on a date, usually the way to force someone to slowly fall in love with you is to ask them a fuck ton of questions. Which is my strategy. I go into dates with a sort of competitive attitude: I WILL WIN THIS DATE!
How do you know who wins a date? Simple. Whoever talks the most is the loser. Because they’ll end their night feeling good while doing absolutely nothing to make their date feel heard. They’ll think they’ve been charming when really they’ve just been completely self-absorbed and annoying. So if you’re on a date and you’re realizing you’re talking a lot, you better start asking some goddamn questions or your reputation will be tarnished forever - I will personally make sure of it. Here are a few of questions that work in almost all situations:
Where are you from? (And follow ups like “how was it growing up in “_____
”?).Do you have siblings?
What are you excited about this year, work or life wise?
Are you a Tonya or a Nancy? (Sidenote: NEVER date a Nancy!)
Have you ever read a book? If so please explain.
What did you want to be when you were little?
Do you remember math?
What’s your favorite style of architecture?
Do you have any gossip you’d like to share?
Have you seen the Netflix show about the lady with the big hair and the murders? (This should work at any time regardless of whether you’re referring to a specific show or not).
See? Wasn’t that easy? But for some reason LA Gay Guys (and maybe all guys?) have absolutely no ability to ask a question. And the more attractive they are the worse it gets. I’ve gone on like one thousand dates with attractive actor types who just sit there like wax figures while I ask them questions for hours on end. Sometimes I’m like “well maybe he’s not that into me.” But in that case is literally everyone not into me (possible)? Because it’s been this way on every date I’ve been on since 1982.
So, here’s what I think needs to happen. Guys, ASK A FUCKING QUESTION.
Ask a motherfucking question.
Ask a motherfucking question.
Ask a question and then ask another question and then finally ask another motherfucking question. Got it? No one wants to sit at a table interviewing a dead fish only to get “yes,” “no,” and “maybe” responses. Ask a question or go jump into the nearest well.
Honestly, I think some people are just innately interested in the inner lives, pasts, and desires of other human beings and some people aren’t wired that way. But I have absolutely no interest in dating the latter. If I’m just gonna be interviewing a blank wall, I’d rather just make a scarecrow or buy a mannequin and put it in a corner. At least that way I’d get to dress them in cute seasonal outfits like for Halloween and Christmas or whatever.
Now that I’ve explained how conversations work and the ONE SIMPLE STEP (ask a question) you need to take not to be a total VOID OF HUMANITY, I’d like to weaponize this essay. So if you’ve been on a bad date or chatted on Grindr with someone who is truly terrible at asking questions, send them this. And if you’ve received this link from someone you went on a date with, it’s likely that you lost the date and you need to do some work on giving a shit about other people. Or at least learning to feign interest by asking a goddamn motherfucking question.
Ask a goddman motherfucking question.
Goodbye!
This works in so many situations besides dating. This used to be called “active listening” where you ask a question, LISTEN to the answer and respond to that. Just LISTENING instead of thinking of what clever thing you’ll say next will set you up for conversational success. And who knows where that will lead?
Lol! This post made me think of a couple questions.
Like:
Omg do you remember baby Jessica when she was stuck in the well when we were tiny tots? That was big news back then.
And have you seen that lame quibi streaming service show called Dummy with Anna Kendrick? I think it’s like modern day Mannequin with Andrew McCarthy and Kim Cattrall!
Also you definitely need a sub stack merch side hustle with a cute pastel pink sweatshirt that says I’m Terry and you’re Gross™️