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Top 10 First Date Questions To Foster Connection And Keep The Conversation Going


Dating is a great way to meet someone new who you could potentially decide to bone later. And one of the best ways to get to know your date better is to ask the right questions that can help reveal their personality, interests, values, and goals. There are certain questions you should be asking via FaceTime, zoom, WhatsApp video call, or when you’re finally able to get out. Knowing these things about your date right away can save you a lot of time and effort if you have hard limits, criteria, and specific things you’re looking for in your potential partner. There’s a fine line with being open and communicative about what you want and going a little too far. So with that, here are some solid first date questions you may keep in your back pocket that just may land you a second date!

1. What Does A Typical Day In Your Life Look Like?

Getting to know more about someone’s daily routine tells you a lot about their lifestyle. It can also reveal whether your date is an early bird or night owl or how they prefer to spend their leisure time — all of which can pave way in determining whether or not you would be compatible in the larger sphere of life.

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2. What’s The Best Vacation You Ever Took?

While having different vacation preferences or styles shouldn’t be a deal-breaker, it’s always good to know if you love relaxing beach holidays while your date prefers having a stacked itinerary. Also, talking about your fondest travel memories and the best experiences of your life seems like an interesting and fun topic that can help liven up the conversation, and who knows? Maybe you both took that incredible cruise to Singapore!

3. What’s The Wildest Thing You’ve Ever Done?

A response to this question can give you an idea of how adventurous or daring your date is. It can also pave way for a highly entertaining story that may just ignite that sought-after spark.

4. What Do You Normally Do On Weekends?

Since you’re likely to spend much of your free time with your prospective future partner, it is important to know how your date likes to spend their weekends, or more generally, when they’re not working. Do they like to keep themselves busy with some charitable work, and indulge in other social activities? Or are they party freaks, spending most time clubbing or out with friends? Or do they simply prefer to spend time at home in an attempt to unwind and recharge? This question can tell what you and your date may have in common.

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5. What Are You Most Passionate About?

Most of us love discussing the hobbies and pursuits we enjoy. And this is another question that can unearth what some of their interests, passions, pursuits and pleasures are. The key to knowing someone is to find out what they love.

6. Tell Me About Your Closest Friends.

This will give you a sense of whether or not you would vibe well with your date’s friends, which could be important down the line. It also gives you information about their ability to have long-term relationships and whether they like to keep in touch with people.

7. Have you read any good books lately?

This easy question will give you an idea of their reading tastes. So, try and focus on some favorite books you may have in common. And if one or both of you hasn’t read anything new recently, you may just have the perfect second date idea.

8. What Were You Like As A Kid?

Sharing childhood stories gives the other person a chance to be vulnerable by giving you a glimpse of their younger self. This can in turn help them connect with you and with their younger self in a profound manner.

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9. What Are You Currently Obsessed With?

It’s good to know whether it’s a book, TV show, gardening, cooking, pilates, or something else that your date is currently into. This can help you see if you two share any of the same interests or passions.

10. What Do You Love Most About Your Job?

Instead of blatantly asking “So, what do you do?”, you are in for a treat by asking this question that lets your date talk about work in a positive, emotionally evocative way, rather than just harping on their job responsibilities.

Make sure these questions are not bombarded at your prospective date in an interrogating manner. Let them come up naturally, and hopefully tread way for some interesting conversations. Happy dating!



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