Everything I Know About Dating, I Learned from The Great Gatsby

I won’t pretend I used to know a single thing about the mystifying swampland that is dating. I’ve tried everything to be a better dater—reading magazines, taking online quizzes… I even tried saying hi to someone once, and it went terribly. But it wasn’t until I read The Great Gatsby, otherwise known as the be-all, end-all in romantic instruction manuals, that I learned how to do this thing called dating, and do it RIGHT. Here are just a few of the nuggets of wisdom that I absorbed:

1. Be rich. Girls like that.

2. Find the most unavailable woman in the greater New York area. She’s the one.

3. Absence makes the heart grow fonder. Disappear for five years.

4. You can either accept that she’s the one who got away, or you can dedicate your life to pursuing an ideal as nebulous and unattainable as the American Dream.

5. The most attractive quality in a man is “has a mysterious backstory.”

6. If you don’t come from old money, well, good luck with that.

7. Don’t ever invite her to anything. Throw parties and just hope she shows up.

8. Become friends with her husband.

9. “Old sport” is a good, gender-neutral term of endearment.

10. If at first you don’t succeed, become a bootlegger.

11. Girls like a guy who will take the blame for their vehicular manslaughter.

12. Cute date idea: go to an illegal speakeasy.

13. Cute date idea: take her out for lunch and tell her she’s a bad driver.

14. Cute date idea: confess to your illicit affair. Run over your husband’s mistress. Flee the scene.

15. Just remember: your first love is rarely ever your last love, unless you’re a sexy war hero with something to prove.

16. Staring at your crush’s house across the bay for hours and hours is completely normal.

17. So is collecting newspaper articles about her.

18. If your friend’s mistress tries to set you up with her sister, definitely leave the party with someone else’s husband instead.

19. Love triangles can only be resolved when half the people are dead.

20. If you are Old Money, this is good. If you are New Money, you could at least have the good sense to die of shame.

21. Tips for a successful first date: meet at a mutual friend’s house. Don’t tell your crush that you’re going to be there. Women love surprises. Jump out the window.

22. Money can’t buy happiness, unless it’s the 1920s and your lover-to-be is a southern belle who’s expected to marry rich.

23. Triple dates almost always end with someone getting punched in the face.

24. Some people have a sixth sense that tells them when their spouses are cheating on them. This is a scientific fact, brought to you by Tom Buchanan.

25. You can’t repeat the past, except of course you can!

26. It’s the 1920’s, so everyone is cheating on their spouse, apparently. That’s just something that’s happening.

27. If your husband is a racist and also cheating on you, you should probably stop being married to him. But that’s just me.

28. When you inevitably reunite with the woman you love, force your friend, the perennial third wheel, to go stand in the backyard so the two of you can catch up.

29. If you ask her out and she says she’s marrying someone else, that’s a maybe.

Still need help in the dating department? Try Everything I Know About Dating, I Learned from the Wife of Bath’s Prologue.