Jay Gatsby’s Guide to a Successful First Date

If there’s one thing I learned from every last single “old sport!”-laden sentence of The Great Gatsby, it’s how to go on something akin to a date. But don’t take my word for it—let’s turn things over to the expert himself for a little Q&A action. If you do not acquire upwards of 50 dates as a direct result of reading this, I will be shocked.

Q: So there’s this girl. I like her, but we can’t be together. What should I do?
A: I’m going to assume that you guys can’t be together because you’re but a poor soldier of humble origins and she’s a wealthy Southern belle with a pretty face and no sense of personal accountability.

Q: Obviously.
A: Right. So I’d start with proving your worth by acquiring lots of money through unscrupulous means. Girls like that.

Q: Okay. So what’s next? How do I ask her out?
A: Whoa there. Let’s slow it down. Let’s take it easy there, buddy. You’re lucky I’m an expert on this sort of thing. Do you think girls like a guy who shows initiative? Of course they don’t! Girls like a guy who’ll hook up with them, fade into obscurity for a couple years, maybe five, and only briefly resurface to taunt them with cryptic love letters the day before they marry another man! This is basic stuff!

Q: And then I ask her out, right?
A: We’re at least 43 steps away from actually asking her out. I feel like you’re just not getting this.

Q: Sorry.
A: It’s okay.

Q: So flirting? Is that what happens next?
A: In a manner of speaking. What you’re going to want to do is buy the mansion directly across the bay from hers and then throw a couple of parties for her benefit, all without ever actually inviting her or even speaking to her. Just stare at her house from time to time. Like really eyeball it. As for the parties themselves, I’m talking big. I’m talking extravagant. I’m talking people getting run over in the driveway and guys fighting hobos in your garden. Real ragers.

Q: What if she doesn’t live near a bay?
A: Then I can’t help you. God, you’re making this difficult. Anyway, cultivate a widespread reputation so she’ll hear talk of your riches long before the two of you actually reunite. You want your sexy cufflinks to speak for themselves. I think this courtship is going well so far. How do you think it’s going?

Q: I’m not sure. In this hypothetical courtship of ours, I haven’t seen her in five years and also she’s married to another man.
A: Perfect! We’ve got her right where we want her. Now, coordinate a secret meeting between the two of you using as many mutual friends as you can muster, just to make things even more needlessly complicated. Don’t forget to jump out a window at one point and throw your shirts everywhere. This will be very sexy.

Q: Okay, so we’re reunited. That took a while. Are the two of us finally alone together?
A: Certainly not, old sport! Your best friend is there.

Q: Why is he there?
A: Because it’s his house, silly. He helped you set this whole thing up. It’d be rude to ask him to leave, don’t you think?

Q: Speaking of leaving, is she going to leave her husband at any point? Maybe I could get her to run away with me?
A: Yeah, she’s not going to do either of those things. You guys will, however, embark on a secret affair. Her husband will have vague suspicions that will culminate in a loud, heated argument during which he accuses you of being a criminal and she ultimately chooses him over you. Your entire world will come crashing down around you and all you’ll be able to do is watch.

Q: That sounds terrible.
A: It will be. I mean, not as terrible as when she runs over an innocent bystander while driving your car, but it’s up there.

Q: She runs someone over with my car?
A: Yep. You’re so lovestruck that you even take the fall for it. Bet you wish you could go back to writing cryptic love letters and fighting garden hobos, huh?

Q: I feel like I know even less about dating than I did before.
A: Yes, well, I never claimed to be an expert.

Q: That’s exactly what you claimed.
A: You’ve got me there.

Q: So at the end of all this, I don’t get the girl, and I wind up taking the blame for a crime I didn’t commit. Could things get any worse?
A: I don’t see how.