55 Engaging Questions to Help You Dazzle Your Date

Master the simple art of asking questions

You’re going on your first date, and you’ve already narrowed everything down to a T. You know where you’re going, you know what you’re going to wear, but now you’re starting to get anxious because you don’t know what you’re going to talk about.

That’s all going to change once you become an expert at asking the right questions. Here’s what we’ll cover today.

Conversational Skills You Need to Succeed

Being a good conversationalist is at the top of the list of things that will make you succeed, and you need to come prepared. We’ve all heard that women like men who ask questions, and don’t just talk about themselves. That’s why I came up with the ultimate list of questions to ask on a first date.

So when you’re on your date and things start to get quiet, use some of these good conversation starter questions.

None of the questions can be answered with a simple yes or no, so you’re guaranteed a quality conversation.

Without further ado, let’s get into it.

55 Engaging Questions to Ask on a First Date

Now, there are lots of different things that you might want to ask a person, so I’ll leave you with a few categories for you to choose from.

Make sure to pick a category and question that seems most interesting to you, so that you can both be engaged in the conversation.

Casual questions

At the beginning of the date, it’s always good to start with some light and airy questions. No one wants to be back into a corner with a bunch of super deep, personal questions.

We’re going for questions that’ll be fun for both of you to answer and hopefully spark an energetic, enjoyable conversation. Let’s do it!

• What is your favorite song right now?
• What are your top 3 favorite movies ever?
• What would be the most amazing adventure to go on?
• Who is your favorite artist at the moment?
• What is the worst food you have ever tried?
• What is a fad right now that you just don’t understand?
• If you were asked to give a presentation on something with 0 preparation, what would you be able to present on the spot for 30 minutes?
• What do you think everyone needs to try at least once during their lifetime?
• If you could be teleported anywhere in the world instantaneously, where would you go?
• What fictional world are you dying to visit?
• Who is the band you’ll always listen to, without a doubt, when you can’t decide on what to listen to?

Personal questions

Now, this next set of questions is definitely more personal.

Make sure you and your date are up to answering these types of personal questions and make sure you suss out the vibe before asking any of these!

You’re about to learn a lot about the person you’re on a date with. Make sure to follow up on your questions with a “How so?” or “Why is that?” to ensure more conversation with ensue.

• Who is someone you look up to?
• What is something you’ve been meaning to accomplish for yourself, but haven’t made enough time for it?
• What book has impacted you the most?
• What are you most passionate about achieving in your life?
• What is one thing you can not live without?
• If you could have dinner with anyone in the world, who would you want to meet?
• Who is the person who has impacted your life the most?
• What does your ideal life look like?
• What was the greatest day of your life?
• What are you most proud of?
• What has been your biggest challenge in life and how have you overcome it?

Fun personal questions

To follow up with those serious, personal questions, you can definitely ask some funny personal questions!

This way, you can still share a laugh, but also get to know the person you’re on a date with a little more deeply.

• What’s one of your biggest pet peeves?
• What’s one thing you do that people think is funny or strange?
• What is something that you definitely won’t be doing again?
• What’s the most embarrassing/funny thing that you’ve done or had ever happened to you?
• What’s something that you’re most likely wrong about, but hold to anyway?
• If your life played a theme song every time you walked into a room, what would it be and why?
• What’s the luckiest thing that ever happened to you?
• If you had to be an animal, what animal would it be and why?
• What’s the weirdest coincidence you’ve ever experienced?
• When people need your help, what is it that they normally ask for?
• What hobby would you want to pick up if time and money weren’t an issue?
• What’s the dumbest way you’ve been injured?
• What is the stupidest thing you ever spent a lot of money on?

Theoretical questions

These types are of questions are always fun because they get the creativity wheels spinning.

These types of questions can lead to serious, deep conversations, or you can keep them light and fun.

• If you knew without a doubt that you could accomplish one of your dreams tomorrow, what would it be?
• If you could have on superpower, what would it be?
• If you could move to any place in the world tomorrow and money wasn’t an issue, where would you go?
• If you could have all the knowledge to have a new career tomorrow, what would you want to be?
• If you could have the answer to any question in the world, what would it be?
• If you had a boat, what would you name it?
• If you could go to space, would you?
• If you could trade lives with a person for one day, who would you trade with?
• What would the funniest “buy 1 get one sale” be? What about the worst? And best?
• If you had to start a business and pick the worst/funniest name for it, what would it be and what would you name it?

Travel questions

Everyone loves to experience new places and new cultures.

Ask your date about places they’ve been, where they dream to go, and more!

• What is your dream vacation place?
• What countries have you visited so far?
• What’s the prettiest place you have ever seen?
• Would you move to another country?
• Would you rather go to the beach or the mountains for a weekend?
• What’s the most interesting thing you’ve learned about another culture?
• If you could go anywhere in the world tomorrow, where would you go?
• Are you a homebody or do you love to travel?
• What was the last adventure you went on?
• Would you ever live in a van and just travel?

Taking the conversation to the next level

Once you’ve gotten things off to a strong start, you can impress your date further by going beyond the superficial. That’s why we compiled a list of what experts have to say about what to talk about on a first date in order to truly get tot know someone.

Now that we’ve gone over 55 great conversation starters

Hopefully, you won’t have to use all of these questions in a single date, but we sure do hope you found this list helpful and fun.

What are some of your favorite questions to ask when you’re on a first date? Let us know in the comment section below.

And remember, always have fun and stay safe on your first date. Screen your date on DateID before you meet to make sure they’re legit and not going to waste your time.