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Here Are 55 Questions to Ask on a Second (or Third) Date

From light conversation starters to questions that build connection

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If you’re reading this, pat yourself on the back—you’ve made it past the first date (hard to come by these days). On that first date, you probably kept things light with questions like, “Where have you traveled?” and “How many siblings do you have?” But on the second date, it’s about getting to know this person on a deeper level—but not so deep that you force your potential suitor into a therapy session. There’s a fine line between mere curiosity and prying into someone’s innermost thoughts (especially before you know their middle name).  

That’s why I’ve broken down 55 questions to ask on a first or second date into five levels. While levels one and two are safer, with questions you could ask a platonic friend, levels three through five are more personal and thought-provoking. Each question, however, will tell you something new—whether it’s what they like, what they don’t like or how they view the world. It’s also worth mentioning that the second or third date should be about getting to know this person without pushing your own agenda. Instead of asking, “What are you looking for in a relationship,” you’ll have better luck if you pay close attention to their responses. While a guy might say he wants something serious, his answer to “What has been the biggest turning point in your dating life?” (number 46 on this list) will tell you everything you need to know about his stance on commitment.

I Tried the Contra-Dating Trend. Did It Help Me Find Love?


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Level 1: Playful but Insightful Questions

Think of these as a warm-up after the first date. While you may have covered favorite foods and what they do for a living, you probably have yet to scratch the surface of what brings them joy. While movies, sports and song lyrics might seem trivial, they can tell you where this person connects and what makes them feel seen. Not to mention that it’s also a golden opportunity to peer into their day-to-day. Items they’d bring with them to a desert island will indicate whether they’re practical or pleasure-oriented—and if they say their house is messy, you can assume they’re far from a neat freak

  1. A movie is made about your life. Which actor plays your part?
  2. Top five current music artists? Or favorite artists of all time? 
  3. What is your favorite song lyric or movie quote you can think of off the top of your head?
  4. What is it about [baseball/journaling/traveling—any interest mentioned on the first date] that you love most?
  5. You’re stuck on a deserted island for ten years, what three items are you bringing with you?
  6. If you could instantly become an expert at something, what would it be?
  7. Is there anything you absolutely cannot do, as in you’ve tried, and are simply terrible at?
  8. If you could have any superpower, what would it be?
  9. Do you have any tattoos? If so, what’s the meaning? If not, would you ever get one?
  10. On a scale of one to ten, how clean do you keep your house? One being clean and ten being a complete disaster.

Level 2: Safe Personal Questions

If you want to get someone talking, these are risk-free questions to ask. Storytelling is the easiest way to engage someone—especially if you get them talking about what they were like as a kid. Add to that the fact that it opens the door for relatability. Again, while the first time their first crush seems trivial, you might relate to passing notes to your fifth grade sweetheart. This, in turn, leads to a more organic conversation about your type, how you were raised or where your passion stems from. 

  1. What were you like as a kid? Were you a troublemaker or a rule follower?
  2. What subject did you thrive in at school? Were there any classes you failed?
  3. What was your favorite book growing up?
  4. Who was your first crush? How old were you at the time?
  5. When was the first time you got drunk? What’s the story?
  6. What’s your earliest happy memory?
  7. What is the most fun you’ve ever had?
  8. What is the most unexpected thing to ever happen to you?
  9. What was the last thing you heard on a podcast, from a friend or read in a book that stuck with you? 
  10. What’s your guiltiest pleasure?
  11. What’s a pleasure that you’re not guilty of?
  12. Would you consider yourself an introvert or an extrovert?
  13. What type of social situation makes you feel the most awkward?
  14. What is the hardest part about what you do for a living?
  15. If you retired tomorrow with unlimited wealth, how would you spend your time?
  16. If you had a million dollars to give away, what would that look like?
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Level 3: Deeper Personal Questions

These questions are better suited for a third date, since they delve into vulnerabilities you probably wouldn’t share with a stranger. While some are relationship-oriented—like who they’re close with—others are about how they view themselves or the world at large. If your date sees himself as an introvert but you find him to be more extroverted, that can tell you something about what he’s like when he’s not “on” (aka at home scrolling through TikTok). Or, if he says he’s more afraid to fail than he is to succeed, it might be a sign that he’s afraid of getting hurt. Either way, the trick is to find one question that sets the tone for the rest of the conversation—and being thoughtful and open-minded with your responses. 

  1. How would your closest friends and family describe you?
  2. Do you think the image you have of yourself matches how people see you?
  3. Who in your life are you closest to and why?
  4. If you could restart your life at any age—knowing what you know now—would you? What age would it be? 
  5. What would your younger self have trouble believing about your life today?
  6. What is the nicest thing you’ve done for someone you care about?
  7. Is there anyone who’s changed your life but doesn’t know it?
  8. What is the best compliment anyone’s ever given you?
  9. Do you think people come into your life for a reason?
  10. What are you more afraid of, failure or success?
  11. Is there a question you’re trying to answer in your life right now?
  12. Is there anything you’ve recently learned about yourself?
  13. When was the last time you surprised yourself?
  14. Is there a moment you wish you could go back in time and change?
  15. What would you never want to change about yourself?
  16. What’s something I’d never in a million years guess by looking at you?
  17. What would you say is your most defining characteristic?

Level 4: Relationship and Learning Lesson Questions

Ah yes, the age-old “ex” question. This might be controversial, but I like to hold off on asking, “Why did you and your ex break up?” (I think it’s hard to package an entire relationship history into one date.) Plus, while they might say it was because their ex-girlfriend cheated, that’s often just a symptom of the disease. That’s why it’s better to keep the relationship questions oriented toward them, and what they’ve learned, as opposed to their ex (and why they sucked). Pay close attention to how they’ve grown, since this is the best early indicator of emotional intelligence

  1. When was your last serious relationship?
  2. What is something that changed your perspective on relationships?
  3. What has been the biggest turning point in your dating life?
  4. What was the hardest lesson you’ve learned in your love life?
  5. What is one thing you’d do differently in your last relationship?
  6. Of the five love languages, which is your favorite?
  7. Do you have any unknown love languages?
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Level 5: Questions About How They See You

Finally, you want to try and get some ‘you’ questions in there. While the second and third dates are all about getting to know them, be wary of overlooking yourself. Asking things like, “What did you notice about me?” or “Was there anything surprising about me?” says as much about you as it does them. If they say something like, “My first impression was that you’re hot,” with zero personality traits to speak to, it might be a sign that he’s looking for something casual. And if he showers you with responses that give you butterflies, it’s a great way to build sexual tension. (Read: Vulnerability is the new foreplay.)

  1. Why did you want to go on a second date with me?
  2. What was it that first drew you to me? (Or made you like my profile?)
  3. Was there anything about me that surprised you?
  4. Did your impression of me change after our first date?
  5. What does my style tell you about me?

Frequently Asked Questions

How Do You Keep a Second Date Interesting?

The best part about a second date is that this person is still a stranger (even if it feels like you’ve known them for a million years). This is what makes it easy to keep the conversation interesting—all you have to do is be curious. Instead of going into it with the mentality of “Does he like me?” try assuming the mindset of “Do I like him?” That way, you’re less likely to be in your head and more grounded in the current conversation. If your date expresses interest in a movie or a soccer game or a recent trip with friends, pick up on what they’re putting down. Simply saying, “Tell me more about that” is an effective way to keep someone talking and delve into where your interests intersect.

What Is Expected on a Second Date?

The only thing you (or your potential suitor) should expect on a second date is kindness and open-mindedness. And by that, I mean actively listening to what they have to say and respecting their interests without poo-pooing them. It most definitely does not mean you’re obligated to go back to their apartment. Nor does it mean you have to sit through a three-course meal if they’re being a jerk. (That’s what the fake ‘emergency text’ was invented for.) But if they’re being respectful of you and your time, you should be expected to do the same for them.

Should You Text Between the First and Second Dates?

I have a whole article dedicated to texting in early dating, but here’s a snippet of when you should hear from them between dates one and three:

  • Max # of Days Before He Should Text: Three days. If you’re going on consistent dates, but you’re only hearing from him once or twice a week, he’s probably not in the market for something serious. I would also advise pulling back your energy if you feel like you’re the only one reaching out after the first date.

In the extremely early stages, texting should become about consistently planning the dates. (This is usually the time when I hear the “he’s a bad texter” argument most.) In terms of consistency, if you go out on Thursday, he’s checking in on Sunday to see what your week looks like. Or maybe, if you went out on Wednesday, he hits you up on Saturday (before 10 p.m., that is—beware of the booty call guy). Either way, the texts should be mostly about coordinating when you’ll see each other next with some small talk sprinkled in. 

In this stage, Niko from The Daddy Academy (aka my favorite TikTok account) puts it best: “There are two main reasons you should be texting: 1) to set the dates. If there’s communication and no date being set, it’s pointless conversation. Use texting here to set the dates.” Then, he says, the second reason for texting during dates one to three is to “create and maintain comfort.” You’re not over-texting to the point where it’s obsessive but you’re maintaining enough back and forth to feel “comfortable with the progression of things.”


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Associate Editor

Sydney Meister is PureWow's Associate Editor, covering everything from dating trends and relationship advice (here's looking at you, 'soonicorns') to interior design, beauty...