30 Dating Questions to Ask To Get to Know Someone Better

As a relationship expert, my mission is to help you stop wasting time on dead-end dates and find someone who’s a good match for you for long-term love. By "good match," I mean you are "in sync" on all 3H's: your head, your heart, and your hoo-ha.

Having coached daters for 20 years, what I have learned is that people want to keep it light and fun in the first three dates, just when they should be getting very serious about getting to know each other. They figure if they can connect on chemistry and banter, the rest will fall into place. Sadly, it usually doesn't.

This is how we waste so much time, and get so fatigued by dating.

Chemistry, banter, and having fun are SUPER important, yes! But you can accomplish all that AND ask the kind of questions that help you:

1) Know someone at a deeper level

2) Suss out any dealbreakers (yours and theirs!)

3) Feel more connected

They have to be the right questions, though, and because you don't want it to feel like a list of questions or an interrogation, you really can't WASTE any! That's why you need to study my suggestions for meaningful questions until you've committed your favorites to memory.

If you’re following my 3-date strategy, you’re aiming to assess compatibility fairly quickly. So this article is meant to give you a great list of questions that ensures no awkward silence in your future, only a scintillating conversation that quickly helps you discern whether it makes sense to proceed to another date.

Great questions for the first date

First-date questions are the most light-hearted questions of the list and they are designed to build warmth between you. It's about discovering the simple things you have in common. This is where you'll get your first impression of someone’s personal life, lifestyle, and sense of humor. 

If you look back on past relationships, you probably realize you learned a ton about the person in that first interaction, even if you then discounted it. 

Open-ended questions are always best. Never yes or no questions, especially the ones that clearly have a right or wrong answer. The goal is to keep the conversation flowing, so think "essay questions" that evoke memories or stories.  These will reveal enough to let you gauge core values, energy, and emotional range—without getting too heavy.

Here’s a short list of questions for your first meeting:

✅ Best book you read in the past year?

✅ What are the qualities of a good friend?

✅ What's a great Sunday for you?

✅ What are your favorite foods?

✅ What is your favorite thing about your mother? What's a favorite memory with her?

✅ Who is your best friend and why?

✅ What are your favorite things to do with your time?

✅ What are your hidden talents?

✅ What is your guilty pleasure?

✅ What’s your go-to karaoke song?

✅ Favorite place to visit? Favorite place to live?

✅ If you could have only 3 things on a desert island, what would they be?

Now for the essay-style questions that should get you longer answers:

✅ What had the biggest influence on you growing up?

✅ Did you ever have your dream job—what was it? Why did you love it?

✅ What makes a great conversation for you?

✅ What do your friends or family tease you for?

✅ What's your favorite childhood memory?

✅ If you could change one thing about this country, what would it be?

✅ If you could change one thing about yourself, what would it be?

✅ What keeps you up at night?

This list of questions is a great way to invite someone to share their life story, personal quirks, and emotional landscape. You’ll hear about their family background, passions, fears, and even what brings them joy. It’s like emotional speed dating, and your true match can handle it just as fast and as deeply as you can.

The importance of light-hearted questions

Men want to make a good impression and show you a good time on a first date. That’s why asking fun questions is the best way to start the interaction and test if he'll go along with it, then if so, you go a little deeper later. Make it easy for the man to win while you're learning some basic facts and developing rapport.

Light-hearted questions lower defenses, make space for laughter, and ease you both into sharing. Pay close attention to how someone responds. Is their body language open? Do they seem curious about you in return? There really may not be a second date if not. If he is leaning in, happily answering, and then asking you for your answers, plus generating a few questions of his own, we're in business!

Remember, the right balance is everything. You should be monitoring that he's not talking your ear off or the other way around, call it out if you need to. 

Both of you talking about your lives and sharing memories is how you build common ground and comfort with one another.

Best Questions for the Second Date

By the second date, you hopefully feel more comfortable and more confident. Now you’re ready to take it to a slightly deeper level. That doesn’t mean skipping to trauma-bonding, but it does mean being a little more intentional.

This is your chance to ask questions about values, relationships, and the way they approach life. Don’t be afraid to bring up things like:

✅ When and how do you recharge?

✅ What's the best time you've had in the last year?

✅ What’s your relationship like with your family? Who are you closest to? Why? Most distant?

✅ How do you feel about social media? What's your relationship to technology?

✅ What would your closest friend say is your superpower? How do they describe you?

Questions like this help you assess emotional intelligence and whether they’re someone who could be part of a healthy relationship. Whereas first date questions evoke light stories and preferences and basic details about life, Date 2 questions go into some stickier topics like relationships. You could even bring up past love relationships, but mostly people like to wait for Date 3 for that. If you tackle family and friends, that's sufficient for the second date.

The Right Questions for the Third Date

The third date is often when you’re deciding whether there’s enough there to keep going—or whether this person just isn’t a match. The best questions at this stage are a mix of meaningful and practical. You have to make sure you're touching on things that are dealbreakers for you.

You might ask:

✅ What does a great relationship look like to you?

✅ When was the last time you felt really proud of yourself?

✅ What are you looking for at this stage of your life? Casual or long-term? If commitment, what does that look like for you?

✅ Have you ever been in love—and what did it teach you?

✅ What’s something you’ve worked really hard to change?

By the third date, you should also add topics that are specific to you and not generic. This is the time to bring up money, sex, past relationships, bad habits, and health issues, yes, even if it's awkward. You don't want to start falling in love with someone who either has issues that are dealbreakers for you or who just can't talk about their issues. This is the time to talk about liabilities, not just assets.

Pay attention. By the third date, you are hoping they are ready to be vulnerable, but you also have to focus on being safe to talk to. Part of this is leaning in and really listening, and part is about you going first, talking about things that might be hard for you. 

Use active listening. Stay curious, and let their answers guide your next question. This is a dance. 

Most people think the thing to ensure on the first 3 dates is that everyone is having fun and feeling flirty, but don't skimp on the depth. That's what the right questions are for!

Choose the place carefully

Location matters more than you think. A crowded bar or noisy restaurant can make it nearly impossible to establish genuine connections. And if you’re shouting over a cover band to hear about their dream job or favorite place to travel—you’re missing the point.

I recommend a cozy coffee shop or a quiet wine bar where you can actually focus. The best gift you can give yourself is a setting that makes it easy to have a great conversation without distraction.

And if you’re someone who tends to get nervous, being in a calm environment will help you stay grounded. 

Want more guidance? Don’t miss my free webinar on how to date with intention: 

Frequently Asked Questions about Asking Dating Questions

How do I keep the conversation flowing naturally?

Start with light-hearted questions that invite storytelling—like asking about someone’s favorite travel memory or hidden talent. Let their answers guide the direction of the chat. When in doubt, say something like, “That’s interesting—tell me more!” It’s not about having a perfect script; it’s about staying present, curious, and open to connection.

How do I avoid making it feel like a job interview?

Strike the right balance by sharing your own stories too. Make it a back-and-forth, not a checklist. Laughter and storytelling help keep the vibe relaxed.

When is it okay to ask deeper questions?

By the second or third date, once trust has been built and the energy feels mutual. If someone’s emotionally available, they’ll welcome a chance to go deeper.

How many questions should I ask on one date?

There’s no perfect number. Let the flow of the conversation guide you. Aim for 5-10 thoughtful questions, plus organic follow-ups, so it doesn’t feel scripted.

What if my date avoids answering a meaningful question?

That’s worth noting. It could be nervousness—or a red flag. If it keeps happening, they may not be ready for the kind of authentic connection you're looking for.

Love,