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The Essay Project 2018: Do essays age well?

So, I've decided just to go with this new loosey-goosey thing we have going at Citizen Reader. Sure, we have an actual Essay Project Schedule (look over in the sidebar), but other than that this reading of certain essay collections and talking about them has been a pretty free-form affair.

And I'm kind of liking it!

So I'm just going to pose questions as I have them. At the moment I am reading, in a very leisurely manner, David Foster Wallace's A Supposedly Fun Thing I'll Never Do Again (which is funny, because reading that book was a supposedly fun thing that I never thought I'd be doing again), as well as David Rakoff's collections Fraud and Half Empty.

Now the first thought I had about these books was, holy shit, I forgot how dense and long that DFW book was. So here's your official Get Out of Essay Reading Free card: don't read the whole thing. Let's just suggest the essay that matches the title, shall we? (Although, actually, I think the first essay, on tennis, is my favorite).

And the second thought I had, while re-reading Fraud, is that I just wasn't enjoying it as much as I did the first time around**. Is that because they are essays that didn't stand the test of time, or (the more likely option) am I just such a different person reading this collection that it's actually like reading a completely different collection?

I know. I actually blew my own mind a little bit, but I don't have a lot of mind to blow so it's easily done.

So my question is this: Do you think, as a general rule, that essay collections "age" very well? What makes an essay (or collection of them) "timeless"?

*No, Half Empty was not assigned reading. I just wasn't feeling Fraud and thought I'd try another collection of Rakoff's to see how that felt.

**This is no slap at Rakoff. If I wasn't enjoying the actual essays or the subjects of the essays as much, I was still loving the person it seemed Rakoff was.