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Sloane Crosley may be an accomplished writer, but shes still humble.

Throughout our long chat, she remained nothing short of great company.

Has the way you approach using humor always the same?

Writing humor forThe New York Timescan be complicated, but your sensibility meshes so well with it.

When I say old-fashioned, I dont mean Elizabeth Mitchell/Joseph Hardwick old-fashioned, although that would be nice.

More theThis American Lifeheyday model.

I didnt have to bend over backwards to fit into someone elses mold, I can tell you that.

You have to amuse people quickly but not at the sacrifice of meaning.

This isnt a Most Jokes Per Square Inch contest.

Is that a result of your becoming more comfortable with ambiguity, with not having those answers?

Sure, thats probably true.

Dorothy Parker said humor should always be used as a shield and not a sword, so theres that.

But maybe the real answer to your question is about the idea of ones own mortality.

I mean, how many books of personal essays am I possibly going to write?

There could be four more, or there could be one.

Its sort of this feeling of taking advantage of the platform and the time you have on stage.

Now its more this idea of This is exactly what I want to say.

The trick is to not become so indulgent or meandering with that.

He was workshopping material on Trump just into the ether, with no regard for the audience.

They dont have to be taken off.

In general, has the way you think about humor changed?

Well, I feel like its a little less pressure to make these jokes every five seconds.

Not bad, just specific.

It just looks like youre trying too hard, which just smells bad.

You have to balance out the humor, otherwise it can be grating.

You dont want to be the guy at the party who thinks hes hilarious.

Its important to not ask to be congratulated for being funny when you write funny.

Thats a good lesson.

Do you have an innate instinct for when things need to be punched up?

I mean, sure.

There are certain things you have to do in writing thats sort of like eating your vegetables.

He or she just has to fire up the door.

So I wouldnt say I punch up my writing so much as I take the indulgent edge off.

Do you think working in those different mediums impacted the way you think about writing now?

Its not about impact, its about trying.

Im not saying this to be an egoist, Im saying it to be a survivalist.

I know thats sort of a blunt answer, but Im not alone.

Action just has to happen at a certain point, by a certain page.

Thats a different medium and a different muscle for me.

They might come after you for unrealistic dialogue, but one doesnt influence the other.

I dont know why that is.

Its not like my people fare any better [in different mediums], but I dont know.

A marathoner needs less help to become a sprinter than a sprinter needs to become a marathoner.

Im not a runner.

But I think you will get asked about this.

Like, not everyone can afford to take cabs to the airport, and you mention that.

How organic was this theme?

What is romantic privilege and how do I get in on it?

So Im glad Im not weird.

But it should be organic or feel organic.

She would constantly be like, I know its not civil war, but…

I know its not the Arctic melting, but….

I mean, its like Im getting shot in the street or anything!

Could be worse, could be the Holocaust!

So Im reading this book and Im going: Yeah, I know that.

Have a little faith that when I want to read about social injustice, Im not turning to you.

Maybe this question is a female thing the expectation that we hedge and apologize and our instinct to that.

You know who doesnt get asked to explain his privilege or apologize for the life hes worked hard for?

Name a male writer.

And she took a cab!

But…oh well?

And, more importantly, funny things happened.

And privilege always depends on whos asking, anyway.

Not everyone gets that.

And you have the ability to wander into the alley behind the store at night and feel safe.

I dont get that.

So lets laugh about it until we fix it.

Both you and John Jeremiah Sullivan have written about the strangeness of interacting with the world of television.

I love that piece of his.

How do I let people in on this lost but rare feeling, a reckoning they can trust?

Its strange to talk about yourself as a characterization of yourself.

It has the potential to heighten your most annoying qualities.

We spend too much time wondering what people think of us as it is.

So to write an essay that asks What do you think of me as a character?

is tricky and strange and I hope I pulled it off.

I dont know if I agree that theres a genre difference.

I think its an equal opportunity issue.

Like I would not put Gary on that list.

And then they take the structure and seriousness the grand achievement of the thing for granted.

Ask all the comedic actresses whove never won an Oscar in the history of the Oscars.

But it doesnt take a great leap of imagination.

So is it any wonder humorists dont like being called humorists even though theyre really obviously humorists?

And shes doing the illustration.

So why turn and into only when its and?

Does that answer your question?

All I know is I dont want to lead people astray.

Similarly, the label of humorist I find to be a little bit dangerous.

Im not writing for Shouts & Murmurs every week.

I have no desire to do standup.

I just dont ever want to disappoint people in terms of what theyre reading.

and Where is my political satire?

and Where is the letter from the point of view of the dog?

then thats not fair to anyone.

Ask me in another ten years if Im not still concussed.