What's your favorite book?

Did you just panic at being asked this? Don't worry, I would too.

Let’s talk a bit about books.

Recently, I encountered a discussion on social media about so-called “red flag books”—that is, the kind of books where, if someone you were on a first date with told you one was your favorite, it would raise serious concerns for you about your compatibility with said person.

The responses were pretty much what you’d expect, and not necessarily ones I’d argue with, either. There were a lot of mentions of Ayn Rand’s Atlas Shrugged and The Fountainhead—the latter a book I’m proud to say I gave up after thirty pages even when I was its target market, an eighteen-year-old architecture student with a slight god complex—plus authors like Bukowski, Palahniuk, Bret Easton Ellis and would-be gurus like Jordan Peterson.

I don’t really have an interest in belaboring that discussion—I haven’t been on a first date in fourteen years, and I don’t spend a lot of time around freshman architecture students—but also, it’s a discussion that’s been done to death.

No, what really got me thinking was a separate discussion that spun off from there, one about one’s favorite books. It’s a conversation that proved much harder for me to engage in.

The thing is… I have no idea what my favorite book is.

If you were to ask me my favorite movie, I could narrow it down pretty quickly. Before Sunrise, or maybe Sneakers. (Go ahead, hack into my power company account. Pay my bill while you’re in there.) Similarly, asking me my favorite TV show gives me no particular angst. (Mad Men or Parks and Recreation.) Favorite album? I might have to give you a list of ten, but I could still pull that list together pretty quick.

Favorite book, though? I don’t even know where to start.

It’s not for lack of reading, that’s for sure—I read (or lately, listen to) lots of books, and I give fresh recommendations weekly in my Friday newsletters. It’s just that the question is both so intensely personal—naming a favorite book feels like it says so much more about you as a person than a favorite movie—and that one’s appreciation of books is often very situational and dependent on when and how you read them.

I’d still like to try, though.

I’m going to talk about a few books I really like. Are they my favorite book? [shrug] Hell if I know! They’re all good books, though, and ones that I appreciate in wildly different ways.

I’d also like to hear some of yours.