Bookstores are the easiest place to pick someone up. Think about it: a conversation topic is usually in the hand of the other person, people often browse quietly and alone (no need for shouting over music or wingmen), it's easy to pass yourself off as just being polite if the person seems disinterested in talking with you. A low pressure, casual atmosphere for even the shyest bookworm.
I dated a guy I met at a bookstore for years, we both were embarrassed to be caught with I Ching (him) and Thomas Friedman's The World is Flat (me) in hand. Somehow we got past the ordeal. I give a longer account of our run-in and other tips on conversations with heavy readers in my book Judging A Book By Its Lover (Harper Perennial, $14.99). Much of the book humorously explains how to fake like you've read any author, what one's favorite author says about their personality, and how to speak condescendingly about the most revered works of literature (a personal favorite section). Here's my insight to bookstore flirting:
You will drive a bookstore patron insane if you interrupt their browsing with some irrelevant, inane comment. Know what you’re saying before you start. If you recognize the author, ask if they’ve read any of the author’s other works and how they like it. Mention you’ve been thinking of reading that author as well. If you don’t recognize the author, say the title of the book but not the author’s name and mention that you haven’t ‘heard of that one’. Both statements are ambiguous enough that you’re not committing to knowing anything about the book but you’re at least presenting yourself as conscious of the lit world. Imagine the horror it would be if you made it obvious you had no idea about the existence of the book <em>Gone Girl</em>? Do you even read the Huffington Post Books blog?
Laugh, smile, do all sorts of normal human things that mean we’re happy and interested, but not that interested. Remember bookstores are also where a lot of crazies go to hit on others by examining their shopping choices (wait a second) - you’re just here to see if these tips work.
No one cares about your book. Let the other person talk. Keep the conversation about what’s in your hand limited to: title, author, how you heard about the book and why you decided to pick it up. Omit any phrase that involves Goodreads or philosophy class.
Don’t ruin someone’s afternoon being pushy over their literary choices. You get two one-word responses in a row? Abandon ship.
If the book you’re carrying is embarrassing to you (I’m thinking <em>Fifty Shades of Grey</em> or worse, one of the later books in the series) explain it away by saying it’s a gift for someone. However, you should never be embarrassed by the books you want to read, and if the person you’re trying to talk to makes you feel bad about your books, they’re probably not worthy of your attention.
Take advantage of long check-out lines. Easiest way to start a conversation is when next to each other in line. Don’t follow someone from the floor to the line unless if the conversation and chemistry is absolutely wonderful. No one wants to get stuck in line with an uninvited flirt.
If you really hit it off, bookstores and coffee shops go hand in hand. Ask if they’d like to try it out. Asking for a phone number at a bookstore seems wrong, too forward. Let it go if they say no to coffee.