Great Conversation Topics for a First Date, According to Characters from Classic Lit

Warner Bros/Great Gatsby


There are so many things that can go wrong on a first date. You might get flustered and accidentally introduce yourself as Jailhouse Bruce when your name is really Lisa, or eat 9 crab cakes before remembering that you’re fatally allergic to shellfish, or fake your own death as part of a really poorly thought-out plan (shout-out, Romeo and Juliet).

Yes, dating is fraught with peril, and the trickiest part is making conversation. Once you’ve covered the basics (likes, dislikes, Hogwarts house, ability to correctly distinguish between your/you’re), what’s left to talk about? A lot, if fictional characters have anything to teach us. Before you embark on your next date, study up on the lit-inspired conversation starters below, and with any luck, you’ll never again experience a silence so awkward that you feel compelled to burst into a tearful and largely inaccurate rendition of “Despacito” just to end it. (That was bad, buddy. That was really, really bad.)

Topics: Books
Tags: harry potter, flirting, dating, classic lit, the great gatsby, first dates, hermione granger, dating tips, holden caulfield, awkward conversations, according to fictional characters, classic lit characters, picture of dorian gray, (definitely not) guaranteed to get you a second date

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About the Author
Damien Galeone

Damien Galeone is a university teacher and writer living in Prague, where he moved thirteen years ago in search of adventure but instead started teaching English. He lives with a cat who’s plotting his murder and he has written lots of stuff that you can find on the internet. His grandmom ab-so-lut-ely loved his novel Senseless and his book of stories Christmitzvah; otherwise they were mostly ignored. His life's dream is to open a hotdog shop, where his allegiance to mustard vs ketchup would remain 68/32.

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