100+ Fun, Insightful & Deep Questions to Ask on a Second Date

A second date is an opportunity to get to know the person sitting across from you a little better—and to see if you’re really as compatible as you seemed on date number one. But what questions can you ask to get to know them in a more personal way, without getting too personal and totally freaking them out? We’ve compiled a list of the best insightful, flirty, and deep (but safe) questions to get to know someone on a second date. We’ve organized them from “least intense” to “most intense,” so you can start slow and work up to the tougher Q’s. Plus, we talked to professional dating coaches Sixu Chen and Cristina Morara about how to have a great conversation on a second date. Keep reading for the deets!

Best Questions to Ask on a Second Date

Are you more of a texter or a caller?
What type of music do you like, and what’s the last concert you went to?
What was your favorite Halloween costume ever? (And how do you feel about couples costumes?)
When was the last time you surprised yourself?
What is the hardest lesson you've learned in life?

Section 1 of 11:

Playful & Funny Second Date Questions

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Start the night off with some fun and friendly softballs. A date doesn’t have to be an interrogation (and shouldn’t be!), so try warming up to a deeper, more personal question like “Do you believe in marriage?” with something a little more silly and surface-level, like “Who’s your celebrity crush?”^{[1]
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Expert Source

David Chambers
Dating and Relationship Coach

Expert Interview} You can actually learn a lot about somebody by asking lighthearted and fun questions, like these:
- What are your top three favorite TV shows of all time?^{[2]
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- What's your favorite color, and why?
- Do you consider yourself to be neat or messy?
- What type of music do you like, and what’s the last concert you went to?
- Do you like to cook?
- Where is your favorite place to shop?
- Do you have any pets?
- What does a typical weekend look like for you?
- If you were an animal, what would you be and why?
- What is your sun sign?
  - Wondering if you and your date are astrologically compatible? Take our quiz to find out!
- When you travel, do you schedule your itinerary down to the minute, or do you go with the flow?
- What was your favorite Halloween costume ever? (And how do you feel about couples costumes?
- Do you like to travel?
- Do you have any tattoos? If yes, what do they mean? If not, do you think you would ever get one?
- What’s your ideal weekend like?
- What do you like to do in your free time?

Section 2 of 11:

Insightful Second Date Questions

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Start peeling back layers with these friendly but probing queries. Once you’ve spent some time just enjoying being together and laughing, you and your date may feel relaxed enough to exchange some more personal (but still light) questions, like these:
- Are you more of a texter or a caller?
- What's the worst date you've ever been on?
- What’s one thing you’re looking forward to doing this year?
- What was the last book you read?
- What song or musician has had the biggest impact on you?
- What is the hardest part about what you do for a living?
- Where is your “happy place”?
- What type of social situation makes you feel the most uncomfortable?
- What’s the best advice somebody has ever given you?
- What advice would you give to your younger self?
- Would you consider yourself an introvert or an extrovert?
- Is there anyone you’ve lost touch with that you wish you hadn’t?
- What is your favorite childhood memory?
- Do you have any regrets?
- If you could learn any skill with a snap of your fingers, what would it be?

Section 3 of 11:

Flirty Second Date Questions

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Tease them with these flirtatious and romantic questions. A second date is a chance to get to know them more intimately—but it should still be a fun, flirty, sexy time. If it’s not, it might feel a little like an interrogation, which can be off-putting for you both!^{[3]
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Expert Source

David Chambers
Dating and Relationship Coach

Expert Interview} Be sure to sprinkle some flirtatious questions throughout your conversation to keep the good vibes flowing and boost your intimacy:
- Do you like getting flirty texts from me?
- Who’s your “hear me out” character?
- What’s a fact about you that I’d never guess?
- How do you feel about PDA?
- Do you like what I’m wearing tonight?
- What is your favorite physical attribute of yours?
- What’s your favorite physical attribute of mine?
- Who's your celebrity hall pass?
- Are you more turned on by smell, sight, or touch?
- What song puts you in the mood?

Section 4 of 11:

Safe but Personal Second Date Questions

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Ease into a few deeper (but not too deep) questions to draw them out. These questions are perfect for getting a better sense of who your date is and where they’re coming from—but they’re not so high-pressure as to make them clam up.^{[4]
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Expert Source

David Chambers
Dating and Relationship Coach

Expert Interview}
- What qualities do you value in a romantic relationship?
- What is something I don’t already know about you?
- What role do your family and friends play in your life? Do you have a close relationship with them?^{[5]
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- What’s your preference on paying at the end of a date?
- How do you show your appreciation in a relationship? How do you want your partner to show that they appreciate you?
- Do you have any quirky habits?
- How important is _____ to you?
- If you had the power to address any cause or social issue, which one would you choose?
- Do you have any irrational fears?
- Do you collect anything?
- What, in your opinion, is your most defining characteristic?
- What is something you're bad at?

Section 5 of 11:

Deeper Personal Second Date Questions

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Dive a little deeper with these more intimate questions. If they seem receptive to even more personal conversation, try asking a few of these more probing questions about their life, views, and more to see how compatible you really are:
- How would you define true love?
- What is the hardest lesson you've learned in life?
- What do you need to feel supported?
- How do you typically respond if something is bothering you? Say something? Get quiet? Ask for space? Process the situation for a while?
- What do you think makes a good partner? A good friend? What’s the difference between a partner and a friend?
- Who would you consider your support system?^{[6]
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- What’s your approach to finding work-life balance? Is that important to you?
- Is there a moment you wish you could go back in time and change?
- Is there anything you wish you could change about yourself?
- Why did your last relationship end?
- What is something that changed your outlook on relationships?
- When was the last time you surprised yourself?
- What do you fear more—failure or success?

Section 6 of 11:

Second Date Questions About Relationships & the Future

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See if there’s long-term potential for you and your date. After you’ve been enjoying each other’s company for a bit, you may want to ease into some questions about where they see the relationship going—but try to keep the convo casual and easy. Asking these questions in a casual setting after exchanging fun and insightful questions can help take some of the pressure off a conversation about their view on relationships and expectations for the future:
- What are you looking for in a relationship? Something shorter and casual, or something more long-term?
- Are there any dating rules that you follow?
- Have you ever been in a serious relationship?
- How would you describe your dating style? Do you tend to get to know one person at a time or multiple people at a time?
- What are some goals you think we should have for our relationship, and why are those important to you?
- What is your love language?
- How long do you typically date someone before becoming exclusive?
- What’s the longest relationship you’ve been in?
- What’s something you’ve learned about yourself during your single years or from your last relationship?
- What are you looking for based on the relationships that you’ve been in or your time being single?
- What’s your perspective on exes remaining friends after a breakup? Are you friends with any of your exes?
- What helps you feel loved, safe, and protected in a romantic relationship?
- What are your views on commitment, monogamy, or ethical non-monogamy?
- What are your deal-breakers and non-negotiables for relationships?
- What do all your exes or crushes have in common? What do you think attracts you to them?^{[7]
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- What’s something that often triggered you in your previous relationships?
EXPERT TIP

Sixu Chen
Life, Career, and Relationship Coach
Sixu Chen is a career and relationship coach, as well as an accomplished interior designer, based in Bellevue, Washington. She is the founder of SCcoaching Group, launched in 2020, and is a certified coach through the Life Purpose Institute. Sixu specializes in guiding young professionals and multi-talented individuals through transformative self-discovery journeys to design fulfilling career paths. She is the creator of the CONFIDENT Career Creation program, specifically designed to help creative minds find clarity, confidence, and direction in their professional lives. In her relationship coaching, Sixu focuses on strengthening communication skills to build deeper, more meaningful connections. She also fosters a community of growth-minded professionals by hosting Coach Connect, a weekly networking event on zoom that brings coaches together to collaborate, share, and support each other. Alongside her coaching work, Sixu channels her creativity into interior design, partnering with Beth Bloom Designs as an independent contractor. She earned her Bachelor of Arts in Interior Design from the California College of the Arts.

Sixu Chen
Life, Career, and Relationship Coach

Just spend time together and enjoy yourself with the other person. Just be present with each other. If you want to learn anything about the other person, treat them like a friend and not like you're checking a census.

Section 7 of 11:

Second Date Questions About How They See You

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Get a sense of what your date thinks about you with these questions. Whether you want to get a better idea of how they feel about you, or you’re curious how you’re coming off to them, these questions about who you are and how you present to the world can give you some insight into their perception of the person sitting across the table from them.
- What was your first impression of me? Has it changed between our first meeting and right now?
- How do you imagine I am in a relationship?
- What are your views on gender roles and their stereotypes? Do you feel that one person should take the lead in the relationship more in certain areas or that the relationship should be more collaborative?^{[8]
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- Has anything about me surprised you? If so, what?
- What made you want to go out with me?
- What made you want to go out with me again?
- What does my style make you think of? What does it tell you about me?
- What would you like to do with me on our next date?

Section 8 of 11:

Second Date Questions About Values & Beliefs

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Ask these questions to see how your date’s beliefs align with your own. It can be tempting to avoid discussing potentially sticky subjects, like politics and religion, on a first or second date—but if it’s important to you that your partner’s values and outlook on the world align with your own, it may be smart to see where their beliefs and views fall early on.^{[9]
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Expert Source

David Chambers
Dating and Relationship Coach

Expert Interview}
- Do you consider yourself aligned with any particular political party or group?
- When was the last time you voted?
- Do you hold any spiritual or religious beliefs? Does your family?
- What were the holidays like in your house growing up?
- Who in your family are you closest to?
- Do you believe in chance?
- Do you believe in astrology?
- Do you believe in God?
- What are your thoughts on Elon Musk?^{[10]
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- Are there any traditions that are particularly important to you?
- Is it important to you that we’re politically aligned?
- Is it important to you that we’re religious or spiritually aligned?

Section 9 of 11:

Having Great Second Date Conversations

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1
Feeling nervous? Morara advises: “You’ve got to name it to tame it.” “I am a big proponent of being honest,” Morara says. Admitting to your date that you’re feeling some anxiety is likely to “[bring] you closer together.” By being vulnerable with them, you’re likely to elicit compassion in them and foster some intimacy.^{[11]
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Expert Source

Cristina Morara
Dating Coach

Expert Interview}
- Reframing your attitude before going on your date can also take some of the pressure off: “It’s about the mindset,” Morara says. “You're not getting married to [them]...you’re getting a drink. So I really try to downplay it.”^{[12]
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  Cristina Morara
  Dating Coach
  
  Expert Interview}
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Think about conversation topics ahead of time. It’s unlikely you’ll ask your date all of the questions on this list—even if you had the time, asking questions one after the other may make them feel like they’re being interrogated. Instead, Morara advises pinpointing “5 things [you] want to share about [yourself]” on the date, and how you might “[weave] it in” to the conversation naturally.^{[13]
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Expert Source

Cristina Morara
Dating Coach

Expert Interview}
- Her trick? “Ask the question that you would like to be asked of you.” For instance, if you love traveling, you might ask your date, “Where have you traveled?” or “What's one of the coolest places you've been?” Not only will you learn something cool about them, but they’ll likely turn the question back onto you next.^{[14]
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  Cristina Morara
  Dating Coach
  
  Expert Interview}
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Remember that being interesting is just as important as being interested. Morara notes that sometimes on a date, one person may dominate the conversation. It’s typically done in a well-meaning attempt to be impressive, but what often ends up happening is that the other person feels ignored and bored. “The whole point is to share and connect,” she reminds us.^{[15]
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Expert Source

Cristina Morara
Dating Coach

Expert Interview}
- “It has to be a dialogue,” she adds. “[It’s] not about trying to impress the other person…[but] about seeing if there is a connection here, and by doing that, you're sharing, you're going back and forth.”^{[16]
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  Cristina Morara
  Dating Coach
  
  Expert Interview}
- What if your date’s the one doing all the yammering? Morara suggests: “Lean forward, and just gently touch [them] on the arm. I promise you this works.” It’ll “[get them] out of [their] trance” and bring them back to the present.^{[17]
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  Cristina Morara
  Dating Coach
  
  Expert Interview}

Section 10 of 11:

Questions to Ask Yourself After the Date

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Check in with yourself after you meet up to reflect on how things went. It’s easy to focus a lot on the other person during a date—what they think of you, what they expect, what they’re looking for, how to impress them, etcetera. And that’s all well and good, but in the end, what you think and what you’re looking for are vastly more important. So check in with yourself after the date has ended by asking yourself these reflective questions:
- How do I feel right now, having just left them? Excited? Uneasy? Happy? Confused? Tired? Calm? Bored? Eager to see them again?
- Did they seem genuinely interested in getting to know me?
- Did the conversation flow naturally? Is it enjoyable talking to them?
- Did the date feel like it ended too quickly, or am I glad it’s finally over?
- Do they seem emotionally available?
- Does it seem like we’re both looking for the same thing in a relationship?
- Were they respectful of my personal space and my boundaries?^{[18]
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- Whether or not we have great chemistry, do we seem compatible in the ways that really matter? (E.g., do we share compatible values? Spiritual beliefs? Dealbreakers?)

Section 11 of 11:

Frequently Asked Questions

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1
Should you text between the first and second dates? It’s up to you and your date! Texting may make practical sense, as it can make it easier to make plans. But it doesn’t hurt to send your date the occasional funny meme, friendly greeting, or flirty text. You can even ask them on your second date how much they like texting their partners.
- Texting can be a great way to keep the spark alive while you wait to see each other again.
- You can tell them how much you enjoyed meeting them on your first date: “It was so great meeting you! You’ll have to tell me more about your dog Ashley next time we meet up. 🐶”
- Or tell them how much you’re looking forward to date number 2: “Can’t wait to see you again this weekend 😉 I’m excited to try that new bar!”
2
How do you keep the conversation flowing on a second date? Asking rapid-fire questions can make your date feel a little overwhelmed. But sometimes, the conversation just doesn’t flow naturally—especially when you’re nervous! If the conversation stalls, try asking a follow-up question to build off of the current topic.
- Not sure what to say? Lead with curiosity! A simple “That’s interesting, can you tell em more about that?” will show your date you’re interested, and push the convo forward.
3
What is the second date rule? Some people believe that while the average first date may last only a couple hours, the ideal second date will last 2 to 5 hours. This gives you and your date ample time to get to know each other.
- But there’s no hard and fast “rule” about how long your date should last: if you’re having a good time, it may last longer—and if you’re not feeling it, it’s OK to call it a night sooner than you planned.
4
What is expected on a second date? Nothing. While some people may hope a second date ends up with a hot French kiss on the front porch or even a hookup, there’s no rule book for how a second (or third, or fifth, or twentieth) date “should” go, except that you both treat one another with respect and express genuine interest in each other.
- If you leave after your first beer because your date was rude to a server? That’s fair.
- And if you and your date both decide you’d like to turn your second hangout into your first overnight stay? Also fair!
- Just go with the flow, and try not to pressure one another (or yourself) to behave any certain way or do any certain things.^{[19]
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