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In 2015 the New York Times published one of its most popular "Modern Love" pieces ever: “To Fall in Love with Anyone, Do This.” In it, the author attempted to use a more-than-20-year-old study—consisting of thirty-six intimate questions—to see if she and her date would fall in love over the course of one evening.

The point of the experiment was to test the power of intimate questions as a way to build emotional connection. The list of all thirty-six questions used in that study was extensive, and a few of them are definitely good enough to try out on your next date or over drinks with friends (I know I did). But as interesting as the majority of the questions were, like “How do you feel about your relationship with your mother?"; they would be way too emotionally exhausting to whip out on every first date—or any first date for that matter.

On a first date you want to peel the onion, not cut it right in half. After you get through the cursory stuff like, “How was your day?” and “Have you been to this place before?” drop in a few questions that will begin to expose some of those layers underneath the surface, without making your date feel like he is in therapy.

With this in mind, we have provided five questions you might typically ask on a first date, and how you can tweak them a bit to inspire conversation that is insightful, playful, and comfortable.

Instead of: What do you do for a living?

Ask: What do you like about what you do?

If you matched with your date on an app, you may already know what he does for a living. Rather than simply asking him to recite the requisite bullet points, ask him what he likes about his job. Maybe it’s his coworkers, maybe it’s the travel. This question gives insights into not only how your date views his work, but what he values, too. The importance of relationships, adventure, stability, accomplishment—all of these things are tied to what we do for a living in one way or another.

Instead of: Do you have siblings?

Ask: Who are you closest to in your family?

I’ve realized over the course of some very interesting and accidentally invasive first date conversations that it’s important to let people talk about their families in a way that they feel comfortable. Most of the time this is an easy topic (people love their families!) but you never know. Personally, I’m an only child so the sibling question is a bit of a dead end. Asking who your date is closest to opens the door for them to only mention whom they want, and most likely to start gushing about a person they love, which is always telling.

Instead of: What do you like to do in your free time?

Ask: What’s something about you that would surprise me?

I sort of hate the free time question, and it comes up on practically every first date. It’s only natural to want to know how people spend their non-working hours, but I’m more of a show-don’t-tell kind of woman, if you catch my drift. (Oh, you hike? Then let’s go!) The ‘something that would surprise me’ question is way more fun because it’s so open-ended. You could talk about a memory from the past or highlight an interesting hobby you’ve picked up as an adult. This question is also good because it’s a bit of a challenge. While revealing something unique or special about themselves, they will also likely try to impress you at the same time.

Instead of: What kind of music are you into?

Ask: What single artist’s catalogue would you bring to a desert island?

Asking someone, “What kind of music are you into?” is a lot like asking them what kind of food they like. Most people like all kinds of food, and probably several different kinds of music, too. There’s nothing wrong with this kind of broad, sweeping question, but it’s just not that fun. Desert island questions, on the other hand, are always fun.

Instead of: Are you creative?

Ask: What would your Shark Tank idea be?

Again, there’s a way to balance generic questions that allow for lots of sharing, and broad questions that might not actually reveal anything that interesting. That said, this question probably won’t make sense if you’ve never seen the show Shark Tank, but it’s safe to say you’ve probably at least heard of it, right? (Just in case: budding entrepreneurs present their ideas to a panel of industry leaders and compete for investment money.) Everyone has one of those ideas, silly as it might be. Maybe it’s a restaurant that only sells dips and chips. Maybe it’s a travel app or a company that lets you borrow people’s dogs for a day. (Can someone make that real, please?) This out-of-the-box question is a great way to bring out your date’s creative side and spark a truly original conversation.

Photo Credit: Cynthia Chung