What-if Wednesdays: Fictional Literary Date Conversations


A little thing you’re yet to know about me: I immensely enjoy imagined, inter-book conversations between fictional characters. I find it so delightful to have these characters talking inside my head like they exist in one universe and time. This one is a personal favorite of mine, a token of boredom from one humid weekend evening last summer. It’s a conversation over coffee between Jane Austen’s Emma Woodhouse and F. Scott Fitzgerald’s Gatsby—sprinkled with mild sarcasm and playful banter about their respective stance on love that I find befitting for the fickle month of hearts.

Please note that all of these lines are taken straight from the books but I am in no way claiming any of these as my own with any intention to infringe on any copyrights.

Gatsby: I like large parties. They’re so intimate. At small parties there isn’t any privacy.

Emma: One half of the world cannot understand the pleasures of the other.

Gatsby: You see, I usually find myself among strangers because I drift here and there trying to forget the sad things that happened to me.

Emma: Were I to fall in love, indeed, it would be a different thing; but I have never been in love; it is not my way, or my nature; and I do not think I ever shall.

Gatsby: In my younger and more vulnerable years my father gave me some advice that I’ve been turning over in my mind ever since, “Whenever you feel like criticizing any one,” he told me, “just remember that all the people in this world haven’t had the advantages that you’ve had.

Emma: Indeed, I am very sorry to be right in this instance. I would much rather have been merry than wise. You must be the best judge of your own happiness.

Gatsby: I am slow-thinking and full of interior rules that act as brakes on my desires.

Emma: Why not seize the pleasure at once? — How often is happiness destroyed by preparation, foolish preparation!

Gatsby: Reserving judgments is a matter of infinite hope.

Emma: And have you never known the pleasure and triumph of a lucky guess? I pity you. I thought you cleverer; for depend upon it, a lucky guess is never merely luck. There is always some talent in it.

Gatsby: It takes two to make an accident.

Emma: Men of sense, whatever you may choose to say, do not want silly wives.

Gatsby: I wasn’t actually in love, but I felt a sort of tender curiosity.

Emma: It is not every man’s fate to marry the woman who loves him best.

Gatsby: There are only the pursued, the pursuing, the busy and the tired.

Emma: Perhaps it is our imperfections that make us so perfect for one another!


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