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Blog #24: The best way to start a meaningless conversation on OKCupid

Each post is a great fucking adventure

As Seen On
by in Sex & Dating
July 23, 2018 0 comments

As usual, Howie and I have spent a lot of time arguing over every single thing he’s writing to women on OKCupid.  His laptop is open on my living room table.  I’m drinking coffee to get me through what is usually a slow session.  He’s in gym clothes, having come from the gym.

We’re not arguing-arguing.  But contradicting-arguing, the way kids do when they need to prove who is boss, like this:

Howie: She’s cute and seems interesting.

Me: Will you email her?

Howie: No.  Her nose is a little big.

Me: (trying to mask annoyance) Will that matter if you actually like her?

Or this:

Howie: *writes email asking a girl about her camera brands / collection*

Me: Do you know a lot about camera equipment?

Howie: No, I don’t know anything about it.

Me: So if she answers, will you be able to understand her reply?

Howie: No.

Me:  How would you feel about writing something different then? Something YOU are interested in?

Howie: No, there’s nothing else to say.

Strategy #1 for meaningless conversations:  Ask questions you don’t care about.  That will lead straight to meaningless answers you have no response to.

……OK, back to the email we’re staring at now:

“If you had to remake the system from the ground up, what foundational elements would you put into place to make the system more just?”

I’m lowkey keeping it together on the outside.  If this girl is super nerdy, she will love this question.  But, if she buys a little into mainstream interactions, and she probably does based off her profile, she’s going get his email and think, this dude has no normal social skills.

“I don’t know how to follow it up,” Howie says.

“What would you do?” I prompt. He says his email sounds “heavy.” I use this as the opening to take out those wannabe-dissertation words: “foundational elements,” “make the system more just.”

I realize: if you only ask philosophical or meaningful questions in SCHOOL settings, you end up with questions that look like this. But, if you ask philosophical or meaningful questions everyday, you can spin it in a lighthearted way.

So basically, I am asking Howie to do something he never does in his daily life.

Should people ask meaningful or philosophical questions?

Only if they want a meaningful, or intellectual, relationships.  And Howie says this is what he wants.  He argues with this (of course).

“It all sounds so scripted. It doesn’t sound true to life,” he says.

“Wanna know what I think?” I don’t wait for a reply. I am losing patience for these mini-arguments. “It’s cultural.” I’ve said this before.  Americans, no matter what race, are taught to keep things superficial.

As expected, Howie pushes back: “In a conversation this would make sense, because there’s a back and forth.”

“Yeah, but you only get one shot right now,” I argue back.  “No conversation.  You get one email.”

“It just feels like too much,” says Howie.

“You don’t need to ask her about her most terrifying moment in life,” I point out.  “It could just be a question about why she likes that book she’s holding in the picture.”

Strategy #2 for meaningless conversation:  Refuse to share anything personal in a conversation.  Don’t let the person get to know you.

Howie opens up the profile of the last woman of the night. She’s an Asian-American woman.  She has some book titles on the list with the word “feminism” in them, and is a computer programmer. Howie says the only point of interest on her profile is that she mentors young girls in computer programming to fix the gender inequity in the field. But, he says, he’s not interested in learning more about it.

“There is nothing to say,” Howie announces.

“Wait,” I stop. “You mentor people too?”


“In computer programming?”

“Yes, I volunteer.”

“For a program that supports women in tech?”


I force myself not to stare at him. This is ridiculous.  Is mentioning that so obvious that it’s not obvious? Perhaps.

Howie breezes through:

What’s your favorite feminist author?  I’m working for an organization that supports women in tech. How do you feel about feminism in tech?

Strategy #3 to meaningless conversations: Avoid talking about common interests.

Howie’s written a total of 7 emails in the past hour.

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Each post is a great fucking adventure