9 Questions To Ask On The First Date To Guarantee A Second

Big talk or bust.


Kristin Canning |

On the perfect first date, conversation flows smoothly and just feels easy. But no matter how great of a conversationalist you think you are, it pays to go into a date with a few solid questions in mind.

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For one, small talk about the weather only goes so far (like, until your drinks have arrived, if you’re lucky). And two, coming in armed with a set of questions can not only give your date a legit impression of who you are, but also help you figure out if they’re someone with whom you could have a serious relationship. (A little thing called compatibility.)

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“The best conversations dig deep to uncover what matters most to the person sitting across from you and gives you insight into whether their values align with yours,” says Samantha Burns, dating coach and author of Breaking Up and Bouncing Back.

You need that crucial info to decide if you should keep pursuing the relationship – not to mention, asking these questions will show your date that you care about getting to know them for real, majorly upping your chances of going out together again.

“Talking about meaningful topics will build emotional intimacy and help you feel more connected to your date,” says Burns.

So make a mental note to ask these 9 questions on your next first date:

1. What are you most passionate about?

“This is an easy icebreaker since most people light up when talking about their interests, and usually a natural conversation can flow from here where you’re able to find common interests to connect over, or at least learn about something new that they’re really into,” says Burns.

2. What does a typical weekend look like for you?

This is a great open-ended question that can take the conversation in any number of directions. So ask it early, if you can.

“You’ll likely learn about their hobbies, friends, potential drinking or exercise habits, even whether they are a morning or night person,” says Burns. This is must-have info that can clue you in to your lifestyle compatibility down the road.

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3. What is your favourite accomplishment?

Ah, a fabulous Q to give your date a chance to share something they’re proud of and to shine. (Which everyone secretly wants.)

According to Burns, “their answer speaks volumes about what they value, such as their career, education or fitness.” (Did they get promoted twice in three years? Just finish their MBA? Run a marathon?)

This is also a good chance to notice whether they seem confident, cocky, or insecure when they talk about themselves and their successes.

4. What’s your work-life balance like?

To get a good sense of how motivated and driven your date is by professional goals versus personal ones, ask this, says Burns. It’s another chance to see how well you align in your day-to-day life and hopes for the future.

Knowing this answer is also an easy, pressure-free opp to gauge how much you might actually see them if things move forward.

5. If you didn’t have to work, what would you do all day with your time?

“This will tell you a lot about what they value and their personality traits,” says Burns. “Will they want to volunteer in their community, travel the world, play golf, or spend time with a future significant other or kids?” says Burns.

Again, it’s both a fun conversation topic and gives you major insight into how similar you may (or may not) be.

For example, if their answer is “sleep” – and you’re a go-getter – you may not even want that second date, after all.

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6. What kinds of things do you like to spend your money on?

“Many people are uncomfortable talking about money, but this question is a less threatening way to talk about it because what it’s really getting at is what they value,” says Burns. (Again, with the values – clearly that’s some important stuff to get out the way early.)

“It could be experiences, such as concerts or travel; self-care, such as yoga and wellness retreats; or material goods, like the latest tech gizmos or a nice watch.”

See how this aligns with what you value. If you both love, say, exotic holidays, that could be enough of a spark for a match (and more conversation, to boot).

7. What type of personality traits are you attracted to?

“Maybe it’s someone bubbly, outgoing, sarcastic, empathetic, warm, generous, or go-with-the-flow,” says Burns. Don’t be thrown off if they list a few things you don’t think you possess-it’s not necessarily a deal breaker, just more intel on what matters most to them.

“See what they say and try not to let their response influence your own authenticity, since being real and showing up as yourself is the sexiest thing you can do.” (And the most important, if you have long-term on the brain.)

8. What do you value most in a partnership?

This is definitely an “are-we-on-the-same-page” ask. “This question highlights the things they are looking for in a partner and sheds light on what they may prioritise in a relationship,” explains Burns.

If you’re in the market for a lifelong partner, don’t shy away from this Q. Just maybe save it toward the end, since it’s a bit more serious.

9. How do you feel about [insert topic here]?

Don’t shy away from asking your date how they feel about an issue that’s super important to you. A first date is as good a time as any to figure out if you align on the big stuff, “so you don’t invest too much time and energy in someone only to learn after weeks or months of dating that you’d have to compromise too much on what’s most important to you to be with them,” Burns says.

Topics like politics and religion are no longer taboo – “if they are important to you, they deserve to be discussed early on,” says Burns.

Before your date, try identifying three of your core values – things that govern your life and define how you want to live. Then come up with questions to reflect each of them, suggests Burns. (You don’t have to bring up all three, though… even discussing one can be incredibly telling.)

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A few good topics to consider:

– If you’re super spiritual: “Do you practice a religion or believe in a higher power?”
– If you’re extremely family-oriented: “How often do you see your family? Do you talk to your siblings often?”
– If you’re passionate about saving the environment: “Do you recycle?” (No, it’s not a lame question if that’s important to you!)
– If you know for sure you want kids: “Do any of your siblings or close friends have children? Does that make you want a family some day?”

The options are endless and will likely lead to some interesting back-and-forth. Especially if you’re ready to answer them honestly yourself.

Hopefully, you and your date could talk for hours about this stuff, and you’ll have to save some of the good convo for the second date. Which, btw, you’ll totally nail.

This article was originally published on www.womenshealthmag.com

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