First dates are all about getting to know each other. Sharing a good meal, relaxing with a nice glass of wine, and talking the night away. Except when your companion is shy and needs your help coming out of their shell. To make your next first date an unforgettable affair, we’ve rounded up our top 6 questions to ask on a first date.

With these fun and effortless conversation starters, you’ll master the art of first-date charm. Check them out and keep them in mind next time you’re getting ready for a night out with a new match.

Seeking’s 6 Favorite Questions to Ask on a First Date!

Would you rather …?

If you want to keep the conversation light and playful, how about a fun throwback to your middle school days? A good old game of “Would You Rather” is a playful way to break the ice. Perfect for getting to know each other better, without making it awkward. 

What makes this game so entertaining is that no question is too silly. So go ahead and get creative. And while you’re at it, show off your sense of humor. Before you know it, you’ll be laughing like old friends!

What are you most proud of?

When your date’s on the quiet side, it may feel like you’re the only one doing all the talking. But that’s no reason to text your bestie and ask them to bail you out! One of the easiest ways to get people to open up is by asking them to share what they’re proud of. 

Think about it: we all love to talk about our accomplishments. But bringing them up out of the blue on a first date feels like boasting. By giving the person across the table permission to impress you, you’ll get them to open up and learn more about who they are.

What made you want to go on this date?

It’s normal for you to feel insecure when you’re on a first date—especially when conversation isn’t flowing yet. That’s why this twofer is one of our favorite first date questions! It’s a confidence booster for you and a sure-fire way to avoid uncomfortable silence.

Once your date has said some nice things about you and why they wanted to meet you, it’s time to return the favor. Perhaps you find their profession super interesting. Maybe they have a great profile pic. Or it could be that you both love backpacking. As long as you show genuine interest, knowing what you found attractive about each other will make you both feel comfortable.

Do you have a dream getaway or a favorite place on earth?

When you ask this question, you get a peek into your date’s lifestyle and how compatible you two are. Do they love snowboarding as much as you do? Are they the adventurous type? Did you finally find that foodie who wants to taste the world’s most exotic dishes?

Even if you’re into different things, you could still be right for each other. Follow up with “why do you want to go there?” to learn what makes this an exciting destination. Maybe their answer will make you want to add a new place to your list of places to visit.

How does your typical day look?

Wanna catch a glimpse into your date’s everyday? With this open-ended question, you get a good idea of how they choose to spend their time. This lets you know what their priorities are, what a relationship with them could look like, and who are the important people in their lives.

Even if you’re looking for someone easygoing who wants to keep it casual, this question lets you know if they’re a good match. It gives you insight into what type of relationship they have in mind and how that fits with your own interests.

What are you looking for in a relationship?

It’s usually a good sign if this question comes up during the first date. It means you’re feeling a connection and that you’re open to spending more time with this person. Naturally, you’ll want to know if they’re on the same page.

If the conversation hasn’t hinted at what your date’s looking for, the best way to find out is to simply ask. That way, when you make a move, you’ll already know where things are headed!

Not So Good First Date Questions

As a rule of thumb, it’s best to leave the loaded inquiries for future dates. Any questions regarding religion, politics, or other personal issues are not great questions to ask on a first date. Save those serious topics for when you’ve spent more time together and can better understand each other’s points of view.

Remember, honesty and an open mind are the beginning of every great relationship. As you ask questions on your first date, be sure to also express your own thoughts and personality. The key is to strike the right balance between showing interest and sharing yourself with others. This will give you something to build upon when you go on your second date!


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