If you’re the sort of LSQ reader who’s memorized Klingon, Al-bhed, or Elven, I’ve got some books for you.
As someone with a degree in Linguistics, I’m obliged to tell you that the most boring question you can ask a linguist is, “What’s the hardest language I can learn?”
The answer is subjective and dependent on so many variables: What’s the native language you speak? What’s hard to you about the new language? What’s hard to you about your own native language? Have you studied any languages before now? You may as well ask what the hardest subject in primary school or what the most difficult job out there is.
A much more interesting activity with language, and what drew me to the major initially, is to observe those many variables in languages much the way a biologist might observe lichens or wolf packs.
For the language nerds among our readers, I’m happy to recommend the following goodies.
The Sense of Style: The Thinking Person’s Guide to Writing in the 21st Century by Steven Pinker
What it is: a book about how to write nonfiction well. You’ll learn about garden path sentences (the sort that you have to read and reread and reread but still can’t glean the meaning of) and how to avoid writing them. You’ll learn which rules from Strunk and White or Hodges, etc., make no sense and, in fact, were violated by their composers.
Steven Pinker is a well-known and experienced scientist yet he writes so accessibly, even hilariously. (Noam Chomsky, on the other hand, is also a well-known and experienced scientist, yet his writing is notoriously winding and difficult to parse).
Pinker is great at walking the essential tightrope between descriptivism (what’s happening in language, including in the brains of its users) and prescriptivism (AKA ‘how one should use a spoken/signed language’), that can of worms.
It makes sense to have a healthy dose of prescriptivism in orthography and rhetoric. What if I suddenly decided to follow-through for Webster, who wanted to modernize English spelling? What if I forgot the importance of commas in writing, “Let’s go eat, Grandma!”
If you’re the sort of person who wants to red-pen this column (I use too many parentheticals, don’t I?), then Sense of Style is my first recommendation for you. And I think you’ll like it!
Language Files edited by Vedrana Mihalicek and Christin Wilson 
What it is: a textbook introducing key concepts in the science of linguistics. Signed languages are not ignored! (Most of those examples are from ASL, however.) Comics about semantics, Venn diagrams about sweaters and mammals, sentence trees, culture, and context are all explored in a deep yet still easy-to-follow manner with thought experiments and exercises aplenty.
It’s a big book, y’all. But there’s a reason it’s used in many universities as a primer in the science of studying language.
Making Sense of Language: Readings in Culture and Communication edited by Susan D. Blum
What it is: a collection of academic papers, excerpts, and essays in various but mostly sociolinguistic topics. Pre- and post-reading questions and layman terms introductions to each entry are included. Labov’s classic “Social Stratification of (r) in New York City Department Stores” appears, as does Whorf’s “The Relation of Habitual Thought and Behavior to Language,” and Lakoff and Johnson’s seminal, “Metaphors We Live By.”
The best description I’ve read of culture shock and foreign language exhaustion is David Antal’s “A Linguistic Odyssey: One family’s experience with language shift and cultural identity in Germany and France.” The uniqueness of law to its country of practice is illustrated in Yanrong Chang’s “Courtroom Questioning as a Culturally Situated Persuasive Genre of Talk.” Mary Bucholtz’s “The Whiteness of Nerds: Superstandard English and Racial Markedness” from 2001 is now a snapshot at the performative aspects of nerd culture in the past; read it and compare it to nerd culture now.
If you are the sort of person who thinks about the social meaning of language—culture, race, law, gender, power, religion, and all these other intersections manifesting in language, this book is a good reason to at least dip your toes in Language Files (above) for some Linguistics fundamentals; most of the entries in Making Sense of Language are written for peers in academia. Alternatively, if you try to read some and get a little lost, look around a little online and see who else is talking about it. You might find simpler explanations.
Lingthusiasm by Gretchen McCulloch and Lauren Gawne
What it is: a podcast about different topics in linguistics. Each episode runs about 30 minutes, and the transcripts go up, too, if you want/need to read along. This is a recent, current, ongoing update to the previous two, which are a bit older.
Some recent topics have been: “Why spelling is hard — but also hard to change,” “Evidentiality” (something American English really hates, in my observation), “Pop Culture in Cook Islands Māori,” “Why do we gesture when we talk?” and “Making books and tools speak Chatino”.
The creator also has a forthcoming book called Because Internet. Yeah. I thought you’d like that.
The Mysterious Case of the Starship Iris created by Jessica Best
What it is: an audio drama! That’s right. It’s a fiction podcast. The way language is handled in the universe of Starship Iris is so reflective of the variety that exists in our own world.
Not only can you hear about imaginary English dialects across the terra-formed space diaspora (Earth is no more, it sounds like), you can also enjoy a trans translator (I see what they did there) who speaks the modern and archaic form of at least one alien language and hypothesizes about nano-bot cognition and use of pronouns.
In case your head hurts reading all the super sciency books I recommended earlier, I thought I’d leave you with this leap out of reality. Listen, and let it re-kindle that desire you have to explore language and ask questions about the universe.