Here Are The Best Questions To Ask On A First Date (Or Any Date!) To Avoid Awkward Silence, Up The Fun & Find Out if He’s Really Mr. Right

On a date, one of two things will happen – you either totally connect with the other person, and you’re just on a roll, chatting and laughing together…

Or after the initial pleasantries, the conversation stalls, you can’t think of things to say to get the conversation going, and things just become, well, AWKWARD.

Know what I mean??!

Of course we all want the FIRST thing to happen, and NOT the second!

When folks do find themselves on a date when things just don’t seem to be flowing and they hit that awkward silence, people tend to fill it in by fishing for facts about one another.

They’ll ask things like, “So, where do you work?” “How long have you worked there?” “Do you like it?” Blah, blah, blah.

And guess what? Facts are kinda boring. They don’t really provide you enough information to determine if the guy you’re on a date with is the right fit for you and vice versa.

Facts are okay, but they’re one-dimensional. They don’t really get at the heart of someone’s personality.

Another thing that can mess with the flow of a date is when one person gets a little too intense and becomes a bit of a FBI interrogator.

Being on the receiving end of “date interrogation” sorta feels like this:

  • “What are you looking for you in your love life?”
  • “How long was your last relationship… why did it end… and what did you learn from it?”
  • “Where do you see yourself in 5 years?”
  • “Do you want to get married and have kids?”
  • “What are your religious beliefs?”

Whoa… not a good strategy, right?

I can tell you from personal experience that the person asking all of these questions usually means well, but this interrogation-style questioning is still a surefire way to kill the vibe of a date.

And as you know I always keep it 100% with you – I’ve definitely had dates where, at the end, women have said to me, “Mat, I feel like I was on a job interview!”

I used to be so intense that I’d totally put them off! SO not the result I was going for.


best questions to ask on a date

So let’s talk about the best strategy for better dates: Asking high quality questions.

Asking high quality questions does two things:

First, it keeps things interesting and fun. Remember, repetition is BO-RING.

Second, asking high quality questions helps reveal the person who is sitting across from you in a much deeper and meaningful way.

What are his values like? His sense of humor? His general outlook on life? His thinking process?

So here are 10 awesome, high-quality questions that you can ask on a date that will help you get a much better sense, in a much more authentic way, of whether the dude you’re out with is actually Mr. Right or not.

And keep in mind that you don’t want to ask all of these questions during the course of one date…

Choose a couple that feel right to you to keep the conversation as natural as possible. And let his answers and his questions for you help guide the conversation, too :-)

And if you’re concerned about how to bring these questions up during the date, you can always borrow a line from the brilliant film Before Sunrise and just say in a fun and flirty way:

“It’s Q&A time. We’ve known each other a little while now, so let’s ask each other a few direct, random questions and the catch is that you have to answer 100% honestly. Are you game?”

10 best questions to ask on a date

So, without further ado, let’s take a look at the absolute top 10 best questions to ask on a date to keep the conversation, connection and chemistry flowing!

BEST QUESTION TO ASK ON A DATE #1: What was the first time you remember having a sexual thought?

This is a really fun and kinda sexy question to ask! The guy you’re talking to will lean in or he won’t, but either way, you’ll get a lot of information right out of the gates with this question.

best questions to ask on a date awkward kiss

BEST QUESTION TO ASK ON A DATE #2: What was your most awkward kiss?

This is another one that can be really fun and silly to talk about, and can help keep the conversation light and playful!

BEST QUESTION TO ASK ON A DATE #3: What was one of your favorite vacations growing up?

This question will probably give you quite a bit more information than expected about his background, his family, his tastes and so on.

BEST QUESTION TO ASK ON A DATE #4: If you won a $250 million jackpot, what would you do?

I mean, come on... the possibilities are endless to this one, which makes it a great question to ask to spark some really interesting conversation!

BEST QUESTION TO ASK ON A DATE #5: If you could relive one day of your life, which one would you choose and why?

This question can actually lead to some really beautiful, heartfelt answers and has a lot of potential for an in-depth back-and-forth.

His answer will likely warrant a lot of follow-up questions too! For example: What specifically would you want to experience again? Why? What was the best part of that day for you?

best questions to ask on a date rapper name

BEST QUESTION TO ASK ON A DATE #6: If you could give me a rapper name, what would it be?

Okay, now I LOVE this one because it just lightens everything up!

You say, “Okay, give me a rapper name off the cuff, and I’ll give you one too!”

The more funny and off the wall, the better!

For example: my rapper name is MB Light to the Nizzy Explicit. MB Doggie, Vanilla Icy, Explicit Downtown Julie Brown. Maddie Boggy Boggs.

See? Now that’s fun :-)

BEST QUESTION TO ASK ON A DATE #7: If you were told you had one month to live, what would you do?

Now this one is a little deep, but can be really impactful to talk about.

His answers will also tell you quite a bit what is most important to him in life ‒ his family, his favorite pastimes and so on.

BEST QUESTION TO ASK ON A DATE #8: What’s a book or a documentary film that has had a significant impact on your life?

Now for me personally, this one really gets me going. I’m a person who loves to grow. I love to read, study, watch films, listen to podcasts, all of it!

So any insight into the intellect of my date is absolutely fascinating to me. Plus, I just love a good recommendation.

And listen, if you’re a person who likes to expand her mind too, he’ll definitely think that’s mad sexy!!

BEST QUESTION TO ASK ON A DATE #9: If you could trade lives with one person for one day, who would it be?

This is such a compelling question, and another one with great follow-ups…

For example: What would you want to experience? Why would you want to be this exact person? What do you think you’d gain from the experience?

BEST QUESTION TO ASK ON A DATE #10: If you could marry any fictional character, who would it be?

I just think this question is so damn fun!! I was thinking about it for myself and hmmmm…

I think it’d have to be Ariel from the Little Mermaid. She’s so gorgeous, and that red hair just gets me! 😉


Remember that dates shouldn’t feel like work…the key is fun and connection!

All of the questions I’ve just shared with you are meant to ignite great conversation and deeper connection – they’re NOT meant to feel forced or unnatural.

So just choose a question or two the resonates most with you and see how it goes!

If you seem to hit a dead end, all good! Just try another one.

And just know too, that any high-quality man worth you time and energy will very likely find these questions interesting and will be thrilled to engage with you on these topics.

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