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10 Questions You Absolutely Must Ask on a First Date

Got first date jitters? According to relationship and wellness expert Deepak Kashyap, these 10 questions will not only serve to break the ice; they’ll also give you a great deal of insight into a person’s character.

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First date questions you must askPhoto: ShutterStock

1. “How are you crazy?”

Although it’s playful, this question acknowledges a fact that’s hard for some of us to swallow: no matter how easy-going we like to think we are, we’re all crazy in our own way. By crazy, we’re talking those little quirks and idiosyncracies that make us difficult to get along with at times, let alone understand. What’s important from a compatibility standpoint is whether or not your version of crazy matches the other person’s. If it doesn’t, do you have the coping skills (and willingness!) to deal with their kind of crazy?

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First date questions about childrenPhoto: ShutterStock

2. “Do you have any nieces or nephews?”

Not everyone who wants to be a in a relationship also wants kids. Even if this issue isn’t a high-priority to you, it could be for the other person—and one in which there’s little room for negotiation. Although directly asking, “Do you see yourself with kids” on a first date runs the risk of coming on too strong, why not tweak the question slightly by asking if they have any nieces or nephews? The way they respond, and the way in which they describe their role as an aunt or uncle will serve as a good gauge of how they feel about having children of their own.

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First date questions: What's their sense of humour like?Photo: ShutterStock

3. “What’s the funniest thing that happened to you today?”

You won’t stand much chance of finding happiness together if you and your partner don’t share a similar sense of humour. Knowing that you can make someone smile and contribute to their overall happiness lays a solid groundwork for a satisfying, stable and meaningful relationship. Bad times inevitably befall all couples, but if you’re able to have fun and keep the lines of communication open—even during those rough patches—you have a much greater likelihood of getting through them together.

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First date questions: What are you looking for?Photo: ShutterStock

4. “What are you looking for?”

 

Today’s dating scene bears no resemblance to the one that our parents and grandparents experienced. Dating apps aside, we enjoy far more autonomy over our bodies than any generation before us, and can no longer assume that the people we’re dating are looking for an exclusive, monogamous relationship with the ultimate goal of getting married and having kids. Specifically asking, “What are you looking for” establishes clear expectations and establishes the potential “next steps” beyond the first date.

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First date questions: How do they deal with conflict?Photo: ShutterStock

5. “How do you deal with people you don’t agree with?”

No matter how compatible two people may be, there’s no escaping the occasional quarrel, criticism and difference of opinion. What’s important to remember, however, is that it’s not what we disagree about that determines the health of the relationship as much as how we handle those disagreements. The ability for two people to “agree to disagree” speaks volumes to their ability to adapt and adjust—the two qualities required of an intimate human bond.

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First date questions: What are your worst habits? Photo: Shutterstock

6. “What are your worst habits?”

Deep down, we all want to be liked, and there’s nothing more satisfying and reassuring to us than when another person likes us in spite of our shortcomings. As much as we try to hide them—especially on a first date—we’ve all got a few character flaws and annoying traits we’d like to work on, but they’re part of what make us unique individuals and fully-rounded human beings. Dishing this “dirt” (even in jest) will not only help break the ice on a first date; but it also helps you assess whether or not you’ll be able to tolerate the quirkier aspects of each other’s personality.

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First date questions: What are your best qualities? Photo: Shutterstock

7. “What are your best qualities?”

Whether or not they’re in any way objective (or even truthful!) in their response to this question, it turns out you can tell a lot about people simply by the way they describe themselves. A date who describes him or herself as “punctual, methodical and ambitious,” for instance, is very likely career-oriented.

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First date questions: What do you find annoying in others?Photo: ShutterStock

8. “What do find most annoying in other people?”

Shared interests can bring two people together, but shared annoyances can be just as strong an indicator of compatibility. What irritates you, bothers you and just plain sets your teeth on edge sheds as much light on your personality as that which you fancy and admire.

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First date questions: What are your deal-breakers? Photo: Shutterstock

9. Explore your “deal-breakers”

Knowing what you’re not willing to stand for—and sharing that with a prospective partner—is essential. Each person has their own unique set of “red flags” that they’re on the lookout for (often based on past relationships), and a first date is your chance to seek them out. Obviously, you’re going to want to keep the conversation jovial and fun, but you’ll also want to do a bit of digging into these “non-negotiables.” Do you have a hard stance on drug use? What are your expectations in terms of work/life balance? How important is financial independence to you?

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First date questions: Why is your best friend your best friend?Photo: ShutterStock

10. “Why is your best friend your best friend?”

Finding out what a potential partner values—and why—provides a huge amount of insight into their character. Ultimately, you’ve got to be friends with your lover as well, and discovering the mechanics (and depth) of the relationship between your date and his or her best friend can give you an idea of what could be in store for you.

Toronto-based relationship and wellness expert Deepak Kashyap provides mindfulness-based counselling for individuals and groups through the Toronto Mindfulness Centre.

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