Romance is a dance.

Both sides are intimately engaging with each other, twisting and turning with emotion as they attempt to work together to make art that even philistines stand up and applaud.

While this cliche might ring true, its element of spontaneity has been overblown. It’s true that there is ebb and flow and freedom to first, second, and third dates, but there is a lot of behind-the-scenes work that goes into not only having a solid date.

If romance is a dance it’s best that you practice the steps before you hit the dancefloor with your partner.

Look, first dates should be fun, light, engaging, and anything but an interview. That said, going in with a few quality questions can help breathe life into a date, especially if you get a bad case of first date jitters.

To take the lead in this romantic tango you’ll want to come armed with questions to ask a guy that dictate the vibe and help learn about the person across from you.

Questions To Ask A Guy

We’ve been coaching men for over 12 years. We know how they think, what turns them on, and how to get the most from your dates with them. We know from research that these questions are guaranteed to open a man up, learn more about him, and create an amazing date.

Use these questions to guide the conversation and get the most from your dates.

Interesting Questions To Ask A Guy

These questions are designed to peel the layers back in a way that isn’t threatening. Here are some first date friendly questions to ask your next date.

What was the last song you listened to on Spotify?

This is an icebreaker question, but it’s an interesting one – especially if you two are audiophiles.

Bonding over music is easy, fun, and if you two listen to the same jams, it might just mean that you’re compatible. Go a step further and ask him to make a Spotify Blend with you. Spotify will give you two your compatibility score.

Can you tell me a secret about you? Something not even your Mom knows about you.

There are the boring, standard ice-breaking questions, and then there’s this.

The boring equivalent would be… tell me something I don’t know about you (which is everything). This is a spicy question that is asking him to open up and confide in you. Of course, he may not tell you something super deep, and that’s fine. But sharing secrets, even if tiny, has a way of bonding two people together.

Just be sure that if you ask this question you have a solid secret to offer in return.

What did you do this morning? OR What are you going to do after this date?

How a person spends their in-between time tells you everything about them.

This question will tell you what his routines are. You’ll learn the little things like how he treats his animals, what shows he’s watching, what time he likes to go to sleep, if he reads, etc.

We also have a habit of putting ourselves in the best possible light when on a date. If you asked him what his ideal Sunday looks like, you’re giving him a chance to portray himself at his best. A question like this about his mundane habits is less likely to be embellished and will tell you who he really is.

What are you most passionate about? What’s something that excites you?

Before we go any further, I want to say that taken out of context, some of these questions seem a bit odd.

When asking, you want to slot them into the conversation in an organic way. Suddenly switching from music to social causes could be jarring and make him feel like he’s on an interview. Make sure your questions appear as though they naturally arising.

If you feel like you need to preface your question so as to acknowledge its randomness, may say something like, So, changing gears… OR so this is gonna be a little random but…

What’s your most unique pet peeve?

The early dating period is supposed to be light.

It should be fun and full of play and light questions (especially the first date). Learning about someone’s unique pet peeve has a weird way of humanizing them. Learning about an uncommon annoyance someone has with something that most people don’t mind makes the person across from you more nuanced.

That is, of course, the purpose of a conversation: to view the individual you’re speaking with as distinct. 

Is a hot dog a sandwich?

Keep things light.

Sure you can ask them if they want kids, but you don’t even know if you want to see this person for a second date, so maybe it’s best to pocket that one for later (much, much later).

In the meantime, talk about why a hot dog most certainly is a sandwich.  

What’s the most ridiculous thing you heard or learned recently, I’ll go first.

Most Easy Asians are missing a gene that makes their sweat smell. That’s right, it’s a thing. 

This is why it’s important to read everything. The more you read and consume the more interesting you become, it’s that simple.

What’s an unpopular opinion of yours?

Mexican food is highly overrated. Everything is basically three ingredients, tortilla, salsa, and meat, boom.

No reason to start off too strong. Having a disagreement over something small is a great way to joke with your date while learning more about them.

What’s your go-to food? Let’s see if we’re gastronomically compatible…

Sure, it’s safe, but if you’re a foodie, this question is kind of a big deal.

Maybe he says he’s not really into food and that he lives off microwavable meals. Or maybe he loves the same cuisine you do, and boom, just like that you two have the perfect second date planned.

Consider expanding on this topic by asking if he eats healthy, cooks his own meals, and how often he eats out. 

What do you like to do for fun?

Sure, it’s a standard and basic question, but it’s the best way to learn about someone. Ask him what his hobbies are and he’ll tell you who he is. He’ll speak passionately, get excited, and guess what, chances are you two have something in common. If so, ditch the rest of these questions and nerd out on your commonalities for the rest of the night.

Flirty Questions To Ask A Guy

Even if the questions themselves aren’t flirty they will lead you down a flirty pathway.

Here’s what I mean.

What do you like to do when you’re not going on first dates with strangers you met on Hinge?

This will surely get a chuckle out of him.

But more importantly, it’s a flirty way to ask him what he likes to do for fun.

How do you express love and want to receive love?

Basically, you’re asking him about his love language (even the idea of love languages has recently been debunked). Men typically roll their eyes when women ask this, so this question is a different way of basically asking the same question.

With this question, you’re basically asking for the key to his heart. If he says, when people compliment me, boom, there’s your in. Or when he says, when someone touches my head, boom.

Learning how he prefers to receive affection is asking him for the keys to his heart. If he gives them it’s on you to decide how you want to use them. If you want to spice things up, immediately use this information and maybe joke that now you have the key to his heart.

What was your first kiss like?

First kisses are usually pretty awkward.

You don’t know how to move your lips, feel self-conscious, don’t know when to end it, and wonder if kissing then and there was the right move.

While first kisses generally aren’t great, the story of the first kiss is. 

So have fun with each other as you two share first kiss stories, and who knows, maybe this is the perfect segue into your own first kiss with your new man.

Not to mention this question is flirty. It makes both of you think about kissing without putting pressure on each other. Make him think about and be aware of his own body (or even better of yours).  

What’s your biggest turn-on?

This is another question that seeks to have him give you the keys to his heart.

Sure, this question is flirty, but it serves to really open him up and bond with him. He’ll appreciate your earnest attempt to get to know him on a deeper level.

Personal Questions To Ask A Guy

You don’t need to walk on eggshells for the first, second, and third dates – in fact, we want to hear some crunch. 

Playing nice and avoiding more contentious subjects could mean you’re investing in someone who doesn’t share your values. In other words, get to the marrow of life before you get too invested in a man you know nothing about.

Taking the risk and asking personal questions is a must if you want to have an engaging date. Superficial questions are fine for a little while, but you’re hear to get to know this guy not to leave thinking, meh he was nice.

Walk over to the deep and dive in head first.

Do you vote?

Naturally, the next question is, who did you vote for?

Look, these are contentious times.

If you’re a political person, chances are you may be hesitant to date someone from across the aisle. 

As Pew Research shows, seven in ten Democrats would never consider partnering up with a Trump voter. 

If you have dealbreaker questions that you want answered, you should ask them during the early stages of dating.

This question is perfect for getting to know his core values. 

And look even though Pew Research show that dating someone with contasting politics isn’t common relationships comprised of a Dem and Republican tend to be incredibly strong. Tom and Em for one have different political backgrounds. They make it work because they’re both open-minded, and when they have disagreements they don’t become combative but curious.

Don’t discount them if they’re different than you. Every relationship needs a little spice.

What do you think of *the recent contentious new story*?

Another way to put this is, “hey, did you recently here about *insert storyline*?

This will not only tell you whether he reads and keeps up with major happenings, but it’s another way to learn about his worldviews and politics.

It’s a much less aggressive way to talk politics and worldviews than by asking, do you think the election was stolen?

What do you think of the #metoo movement?

No need to only ask softball questions on first, second, and third dates.

Challenge the guy – see what he’s made of. Understand how he thinks, and his values, but always be willing to listen, hear him out, and have a respectful conversation… unless he’s a complete ass.

What’s a skeleton in your closet?

You’re not here to play nice.

You’re here to bond. The easiest way to do this is by cracking your date open and seeing what’s inside. That being said, they could easily deflect and ask you to answer first. Be prepared to share.

Are you religious?

One’s religion is clearly near and dear to the heart.

I’m not saying a different religion is make or break; however, having a different religion could mean incompatible rearing styles, contrasting habits, or, at the very least, a different holiday dinner menu.

Romantic Questions To Ask A Guy

There’s a difference between flirty and romantic. Flirty questions are a bit more flirty, sexual, and superficial than romantic questions. Romantic questions are more than a layer deep.

Have you ever been in love?

Stare into his eyes when you say this. Dare him to imagine a world where you and him fall madly in love and move to France to start a vineyard together.

When he snaps back into reality he might just tell you about his romantic past. Learning about his past romances will give you a glimpse into what kind of partner he is.

Questions To Ask A Guy To Get To Know Him

We’re all layered people. If you ask superficial questions you’ll get superficial answers. Bust out that peeler and start asking more probing questions.

What does your perfect Sunday look like?

Sunday is our day right?

It’s the day of the week where we usually have few obligations and can genuinely do whatever we want to. So ask him what his ideal Sunday is. It’s a much better question than, what do you do for fun? Plus it can easily lead to a second date if you speak up and say you’d like to join him on one of his perfect Sundays.

What are you most proud of?

How do you ask a man what his values are without literally asking him? How do you ask what is important to him without asking that question verbatim?

A question like this will tell you the information you want, but is much more engaging than simply asking, what’s important to you in life?

Having him rewind and introspect for a moment is a great way to get to go from stranger to romantic partner.

Questions To Ask A Guy To Get To Know Him On A Deeper Level

Once you’ve exchanged pleasantries and have spoken ad nauseam about what you’re watching on Netflix it’s time to dig a little deeper. These are questions to ask a guy to get to know him in a more meaningful way.

Do you have a passion project?

Talking about work is boring as hell. You might as well be on a Zoom call with your date if all you’re going to be talking about is KPIs and work drama.

So ditch the work talk and ask him about what he’s passionate about. This will get him excited and talking, and you’ll see his true self really shine through.

What are you really into nowadays?

Get an idea of where he’s at right now in his life by asking this question.

Stay with this topic for a bit as you allow him to open up. Ask follow-up questions and show genuine interest in learning more about him.

Who do you look up to?

Another way to say this would be, who are your role models?

Asking who his role models are is another way of asking him about his values and about the man he wants to become.

If I met you in high school do you think we’d be into each other?

There’s a lot of growth that happens between high school and our adult years. Talking about high school will bring up good and bad times and demonstrate the profound growth that he’s gone through since then.

It will make him reflect, open up, and show you who he really is.

Not to mention this question is flirty. It’ll invite him to flirt and be a kid again – and hey who doesn’t want to roll back the years?

Deep Questions To Ask A Guy

After you’ve asked him the interesting questions, the flirty ones, and the romantic ones, it’s time to go deeper.

Reserve these questions for the third date (unless it feels right to ask him sooner).

Tell me about something super difficult that you went through… if you feel comfortable sharing.

Asking vulnerable questions creates a deep and meaningful connection with your date. It helps you to set your relationship apart from working relationships and superficial acquaintance relationships. Sure, it helps you connect deeply and be vulnerable yourself (be ready to share, this isn’t a two-way mirror).

Only ask this if you’re willing to listen. Only ask this if you’re ready to dive into the depths of his soul. Learning about the struggles he’s been through will bring you two together, but could paradoxically also push you apart.

What was the most impactful moment or event in your life?

This will help them to remember a nostalgic moment which studies show makes someone feel good about you.

Be ready for things to get heavy. If he opens up and releases whatever emotions he has inside be ready to accept what he offers. Only ask this question if you’re ready to be swept up in your feels for a little while.

Questions To NOT Ask A Guy On A First Date

If you’re MegaDating, asking questions as if you were reading from a checklist is the quickest way to turn dating into a form of torture. 

We teach students how to make dating their new favorite hobby.

MegaDating is about releasing attachment to the outcome, about enjoying the process instead of strategically creating the outcome.

Who you feel good with often isn’t someone who checks off the most boxes. 

Enjoy the ride, form a connection, laugh, and challenge each other, but whatever you do, DO NOT ask these questions on a date. 

So, how has your dating life been?

Look, it’s tough out there. We all know it. It can be tempting to ask the other person how the single life is treating them but doing so could easily make the guy you’re dating uncomfortable OR think that you’re not into him.

Even though being single is something you two have in common, there are plenty of other commonalities you’re better off bonding over.

Avoid this by asking instead, what’s your wildest first date story?

How do you feel about casual hookups?

This feels like an interview question.

He’ll feel the pressure to answer correctly. If answered incorrectly he might feel like you’ll stand up and walk away. Don’t ask questions that make him feel like, with one wrong answer, he could screw everything up.

No more do-or-die questions. 

What’s your best pickup line?

This is a flirty and playful question that you can only ask if you two are clearly getting your flirt on. If not, pocket this one until it’s obvious you two are in heat.

Not to mention that the line, Are you a time traveler? Because I can see you in my future! won’t exactly make you want to take your pants off. Careful what you ask for.

What’s your type?

This is another checklist question – and it’s where women go wrong when dating. 

Sometimes women feel pressure to quickly weed guys out. To ask a few dealbreaker questions so they know not to invest their energy into a guy. The reality is that you won’t know who he really is on a first date despite asking your entire laundry list of checklist questions.

The only way to know him is to enjoy an interesting conversation where you two are learning about each other and feeding off one another in an organic way.

Leave the checklist at home. Just be open to the person across from you and try to see them as the nuanced human they are instead of immediately trying to figure out if he’s marriage material.

Do you want kids?

Now I have a question for you – do you want a second date? 

Honestly, this question is probably redundant. Chances are you two met online and he wrote whether he has or wants kids on his profile. Not to mention you can filter users by their familial preferences.

What’s something you absolutely won’t compromise on?

Maybe it’s spending Sundays with the boys watching football. Maybe he hates giving oral sex. Or maybe he just really dislikes house music and refuses to allow it in the car or home.

This is another dealbreaker question that could ends things before they even get started.

What’s your relationship like with your parents?

I’m not sure how you would even organically ask this.

If you two chat about families then great, if he wants to talk about his parents cool, if not, no worries. You’re here to learn about him, not his folks.

If you absolutely must ask this question, spice it up and ask something like, people always talk about which child parents like more, let’s switch it up, which parent do you like more? 

When asking a potentially vulnerable question like this, be sure to smile, laugh, and signal that you don’t want an emotionally charged answer about how your date was abused as a child and one time his parents left him at a 7-Eleven.

Are you satisfied with your career?

Honestly, about only half of Americans are satisfied with their job. 

If you need your man to love what he does you’re basically saying you don’t want to date half of Americans without knowing anything else about them.

Avoid talking work.

Dating Decoded

Want to know how to have more effective dates?

At emlovz we teach you the ins and outs of modern dating.

You’ll learn the best questions to ask a guy on a date, how to meet men online and in IRL, how to qualify them, MegaDate, and much more.

Team up with us and our team of dating experts to find not just a partner, but your ideal partner in no time

Our Team

• Emyli, co-founder, curriculum developer, head coach, and host of weekly coaching calls.
• Thomas, (me) co-founder, and coach. If you ever wanted to know what the man you’re seeing is thinking, just ask me.
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If you’re ready to find your forever partner, book a Zoom session with our team today. Together we’ll talk about your dating history, your goals and show you how our program, Dating Decoded, can help you find your ideal partner.