What Are the Best Questions to Ask on a First Date? Or, the Art of Making Good Conversation

First dates are many things, although I’m not really sure I’d call them fun. Upon sitting down opposite a potential new partner over a coffee, a beer, or whatever, most of us immediately find ourselves faced with a dilemma: What do you talk about on a first date? Christian Rudder, co-founder of the online dating site OKCupid, has some suggestions… although to be honest, I’m not sure his suggestions go far enough. Here’s the deal — and how we can take the initial idea further. Conversation, after all, is an art, so mastering it is one of the best skills you can acquire.

The Statement:

In a piece currently running on The Guardian, Rudder — who’s still doing publicity for his book Dataclysm, it seems — offers a series of “secrets” to successful online dating. One of those secrets, of course, includes the sorts of questions one should ask on a first date. Says Rudder:

“People tend to run wild with those match questions, marking all kinds of stuff as ‘mandatory,’ in essence putting a checklist to the world: I’m looking for a dog-loving, agnostic, nonsmoking liberal who’s never had kids — and who’s good in bed of course. But very workaday questions like: ‘Do you like scary movies?’ and: ‘Have you ever travelled alone to another country?’ have amazing predictive power. If you’re ever stumped on what to ask someone on a first date, try those.”

The Problem:

This makes a certain amount of sense; once you get beyond the standard “must love dogs” demographic questions, you’ll learn a whole lot more about someone’s personality and whether or not you’re compatible by talking about their likes and dislikes. What questions like “Do you like scary movies?” and “Have you ever travelled alone to another country?” do right is make it about the other person—but I would argue that those questions will also only take you so far. They’re closed-ended yes or no queries, which can very easily cause a conversation to grind to a halt: “Do you like scary movies?” “No.” Silence. “…OK then…”

The Solution:

There’s an art, however, to turning a closed-ended question into a conversation: Follow it up with an open-ended question or two. Take, for example, the scary movies question. If the answer is no, you can ask what kinds of movies they do like and why; or if it’s yes, you can ask what their favorites are and why. And if they don’t watch movies at all? Maybe they’re more into television, or plays, or books. Or maybe they spend their spare time doing something else entirely. As Harvey Deutschendorf wrote on Fast Company:

“Good questions are asking someone how they think or feel about something that they are talking about. If you’ve talked to someone before, ask them about things that they volunteered in the conversation before. Likely, if they brought up something on their own, it is of interest and some importance to them. Ask yourself what other areas that are related to their interests that they would love to talk about.”

The Next Level:

And when you’re on the receiving end? Help by arming the person sitting across the table from you with what the Thought Catalog piece “One Simple Habit That Will Make You Great at Conversations” calls “conversational ammo.” Instead of answering yes or no, or answering a question like “Where are you from?” with a one-word response (“New York”), elaborate on your answer: “Do you like scary movies?” “No, but I’m a big fan of thrillers. Ghosts don’t really do it for me, but I love suspense.” That allows your partner to ask any number of follow-ups: What’s your favorite thriller, what about ghosts doesn’t do it for you, what are other “suspenseful” activities you like doing, and so on.

These tips, by the way, are applicable in a huge variety of situations beyond dating. Job interviews, meeting your significant other’s parents for the first time, making new friends… the list is endless. Having awesome conversation with thoughtful people is one of the best things in life, so let’s enjoy it, shall we?

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