36 Questions To Ask On A Second Date

Dating experience | | , Editor-in-Chief
Updated On: October 10, 2023
questions to ask on a second date

What are the right questions to ask on a second date? This question ought to weigh on your mind if you’re gearing up for a second rendezvous with a potential love interest. After all, the second date is a more precarious territory than the first in many ways. The fact that you’re meeting again stirs up hope that you may be able to take things forward and transform this initial connection into something substantial.

With that hope, comes the pressure of checking all the right boxes. And one of those boxes is, what to talk about on a second date. You want to seem interested and invested without coming off as too strong or overstepping your boundaries. That’s why knowing what to ask and what to steer clear of can help you meet second-date expectations successfully.

36 Questions To Ask On A Second Date And Why

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As they say, the second date is the real first date because this is where you can begin to let your guard down. And the process of getting to know each other begins in true earnest. The fake laughs will subside, you won’t be riddled with too many insecurities, and in short, you won’t be stiff as a stick this time around.

If you’re already panicking about what to do to have a successful second date, let us remind you: It is a vicious rat trap to fall into. Soon you’ll be overthinking how every single strand of hair on your head looks. Take it easy, your date decided they like you enough to warrant a second date! While there is an abundance of advice on the mistakes to avoid on a first date, you may feel like you’re pretty much on your own thereon.

Well, not anymore. We are here to help you get past the second most important milestone in your dating journey. With these 36 on-point questions to ask on a second date, you will never have a tongue-tied moment:

1. What did you do after going back from our first date?

This may come off as one of the unexpected questions to ask on a second date but it can truly give you an insight into what to expect from this meeting. Did they call their BFF as soon as they left the place where you met? Was there a dissection of the date over wine? Or did they just get on with their life?

If their response is on the lines of the first two scenarios, you can set your second date expectations a tad higher. If not, you may have to step up your game to take things forward.

Related Reading: The Ultimate Funny Online Dating Questions

2. Do you remember (insert the moment)?

What to ask on a second date to not bore them? This can be an easy and safe way to break the ice if either of you is feeling awkward or shy. Bring up a random but interesting incident from your first outing and ask your date if they remember how it went down. If it was something funny, it can get you both cracking up and ease the atmosphere. It can prove to be a great conversation starter.

This may not be the most flirty question to ask on a second date, but sometimes you need to get the laughter rolling before you can bring on your flirting skills. Flirting too soon into the date might just mean you’re eating dessert alone.

3. How did your love for dogs begin?

questions to ask on a date
Build upon something you already know about your date

Running out of things to talk about on second date? Building upon something you already know is a smart way to keep a second date interesting. If your date is a dog lover, you can ask them about how and when they discovered their love for pooches. Or cats, if that’s their first love. Trust us, 2nd date questions don’t have to be rocket science.

It can open the gateway to some interesting stories about their first pet and all other furry friends who have had a special place in their life. You never know, it can turn out to be one of the most thought-provoking questions to ask on a date. It will help you get to know them better.

4. So, what prompted your decision to move to (insert city name)?

At this point, you may already know for how long your date has been living in the city you’re in and the broader details of why they moved in the first place. For education, job, and so on. You can ask them what instincts drove that decision, making this one of your second date conversation topics. Your date may not have given any real thought to the underlying reasons for their choice, which can bring on some moments of introspection.

Related Reading: 70 Questions To Ask Your Crush And Know Him Better

5. What made you stay?

Was it the love for their job? Having found a home away from home? The general vibe of the place? Why did your date decide to stay on? This question can make you find common ground as you discover that you both love or despise the same things about the city you call home.

When you have the right questions to ask on a 2nd date, you’ll be making all the right moves, uncovering the right information. When you find out what makes them stay here, you’ll be better able to grasp their personality.

6. How would you narrate your life journey in under two mins?

If you want a quick recap of your date’s life, then this is one of the second date questions to ask her/him. Ask them to narrate their life journey to you in under two mins. You could go next. There is a good chance that some hitherto unknown details will spring out in the process, and you can learn new things about each other. Keep an eye and both ears open for some red flags in this talking stage, though.

You can ask as many follow-up questions as you like and make the conversation flow uninterrupted. Before you know it, the waiting staff is standing over your head asking you how long you intend to stay past closing time. If that happens, forget trying to decipher what to talk about on a second date, now you’ll have something to talk about on the third date!

7. What is your life plan for the next five years?

This becomes one of the most important questions to ask when starting a new relationship to assess someone’s future goals. Your date’s response will give you a clear understanding of whether your life goals converge or are at least compatible. Based on that, you can decide how seriously you want to pursue a potential relationship with them. Do they see themselves in a loving relationship in a cute little apartment or do they want to move to Tokyo to live the high life?

This is also a smart way to phrase the ‘where do you see yourself in five years’ question. After all, you don’t want the date to start sounding like a job interview.

8. What made you agree to a second date?

What to ask on a second date to know if they are interested in you? How do you even know if the first date went well? A recent study shows that certain behaviors can increase the likelihood of securing a second date. For men, it’s demonstrating better etiquette, which includes being kind and showing good manners. For women, it’s to demonstrate greater involvement, via eye contact and laughing. So, among the mildly flirty questions you can ask on a second date, this one will surely elicit praise and compliments for you.

Of course, you can reciprocate with your own reasons for going out with your date again and let them know all that you appreciate about them. Try to stay within a reasonable range of giving out compliments, though. If you give too many, you might just come off as too … eager. On the other hand, too few compliments will make you seem like you couldn’t care less.

9. What do you see as commonalities between us?

If you and your date are getting together again, you both must have felt some kind of a connection. And that means you see a shared ground, some commonalities over which you’ve connected, no matter how superficially for now. So, dig a little deeper and see what more you can discover about each other to turn this connection into a stronger bond. Make this one of your second date topics of conversation.

Related Reading: What Does A Third Date Mean For Guys? Third Date Conversation

10. What has been your worst heartbreak?

The second date is a safe space to venture into past relationship territory. This is one of the past relationship questions to raise on a second date. Asking someone about their worst breakup experience can break down the walls people tend to build to protect their vulnerabilities. You may get to see a raw, untouched side to your date.

11. Why did your last relationship end?

Another one of those crucial questions to ask when starting a relationship with somebody new. The idea here is not to see where the blame rests for a past relationship not working out, but to assess how your date feels about it now and how they healed a broken heart.

If they’ve healed and truly moved on from their earlier long-term relationship, they will be able to lay out the facts pragmatically and without getting triggered emotionally. But if they seem to be agitated or angry by this question, clearly there are some unresolved feelings at play here. Perhaps, they’re not over their ex yet. In that case, our quick tip is to tread forward carefully.

12. What are you looking for in a relationship?

relationship questions to ask on a second date
Figure out whether your expectations and goals align

Wondering whether such relationship queries qualify as acceptable questions for a second date? We say, go for it! Why keep beating about the bush and string each other along if your relationship expectations and goals just don’t align? In fact, consider this one of the more high-priority second date conversation topics.

If you’re looking for something casual and your date is hoping to find their forever partner, it’s safe to say things are not going to work out between you two. No matter how strong a connection you feel. On the other hand, if you both want the same things, you can take things forward and soon.

13. What do you value most in a relationship?

Do add this to the list of relationship questions to bring up on a second date if you want to explore the possibility of a future with this person. Love, romance, trust, respect, communication skills – What is it that they value the most? And does it align with your relationship expectations? This is one of the second date questions for guys and girls to make sure you two are looking for the same thing.

The answer to this question can be a key determining factor for the course your relationship may or may not take in the future. Such 2nd date questions can be a great way to assess how well you two will get along.

Related Reading: 21 Dos And Don’ts When Starting A New Relationship

14. Has anyone told you that your eyes have a hypnotic charm?

Good second date questions are those with a little bit of flirting involved. In case all the relationship and future talk starts to feel too heavy, you can mix things up with such flirty questions to ask on a second date. Make sure you don’t use the overplayed compliments like “I love your name” without even knowing what their name means. Compliment their eyes or, even better, compliment their personality. They’ve probably worked hard to cultivate it.

Flirty questions to ask on a second date can be a compliment your date wasn’t expecting to come across. Your date is bound to blush and chuckle at this. A slight touch here or a tap there can truly take your chemistry to the next level.

15. What is your happiest memory?

This question is a smart way to keep a second date interesting. You’re giving your date a chance to take a trip down memory lane. Thinking of all the happy moments of their life is surely going to uplift their spirits, and the energy of your date, even more. When you’re thinking about how to not bore your date, all you have to do is ask questions that will bring back happy memories.

Of course, when they share that memory, you will learn something new about them. That’s why this is one of the best second date topics.

16. What is the one thing you regret missing out on?

Letting a dream job slide, missing that coveted college admission by a whisker, regretting a divorce, not dumping that jerk ex sooner … Everyone has that one regret that keeps them up at night. What will follow is a whole conversation about why they’re so passionate about whatever they missed, and then, what you missed out on yourself.

When you’re thinking about what to talk about on a second date, use open-ended questions like these that develop further conversation smoothly. This will help you get to know them on a deeper level.

17. How has your online dating experience been?

If you’re meeting someone you didn’t know before, there is a good chance that you connected on a dating app. Needless to say, anyone who has been on the online dating scene long enough has some horror stories to share about creepy matches and all the red flags they’ve encountered. You could swap stories and share some hearty laughs to keep a second date interesting.

You can even consider this as one of the more funny questions to ask on a second date. Remember, past dates will always provide you with good second date questions to really get to know someone.

18. ‘Family’ is one of the vital second date conversation topics

Who is your favorite person in the family? Make this one of the questions to ask on 2nd date if you’re genuinely interested in the person. One’s family is a huge influence on their personality. This question opens the door to more interesting discussions about family values, dynamics, quirks, and eccentricities.

Once again, remember, the idea here is not to judge but to truly understand what makes your date the person they are.

19. What is the one dating rule you never break?

You can set some unspoken ground rules of dating by asking this question and can manage your expectations better, going forward. This query will help you understand the other person’s second date expectations and set yours accordingly. Do they wait a certain number of dates before starting texting? Will they reach out to plan the next date? Or want you to take initiative? Do they have dating rules about when they kiss, sleep with, or have a sleepover with a potential partner?

stories about dating

20. How long should one wait before sleeping with someone?

Tricky as it may sound, do add this to your list of relevant questions to ask on a second date. By keeping it generic, you prevent the risk of coming off as a creep who is just in it for the action. At the same time, you can get a clear idea of how soon or late things can progress on the intimacy front, and whether you can now act upon the sexual tension which has been brewing.

21. Is kissing on the second date okay?

If you didn’t seal the first date with a kiss, this is one of the flirty questions to ask on a second date that can truly help your cause and help you establish some physical intimacy. By kiss, of course, we mean a proper, passionate lip-lock and not a peck on the cheek. If your date blushes on hearing this and their body language seems welcoming, you can make your move.

Whether you do it right there or wait till the end of the date depends on you and the circumstances. But make sure this is one of the second date questions to ask him or her if you feel ready to take the plunge!

22. What is your biggest fear?

If you two have had some deeper conversations on the first date already, then this is a great question for your second date. Clearly, you two have been opening up more and more. And discussing fears is a great way to create a rapport and establish some emotional intimacy.

23. What is your favorite way to spend your free time?

Do they love taking their dog to the park or whip out an adult coloring book when they have some time off work? This is one of those conversation starters that can also help you make a future plan together, perhaps for a third date. If they say they like to visit a coffee shop to read a book, you can consider asking them if they’d be open to spending time with you there some time next week.

24. If you could ditch your current career goals, what would you do?

Let’s be honest, the current corporate system isn’t doing anyone any favors. We all wish we were off raising horses on a farm, painting in the middle of the street, or simply dancing in a studio all day. This is one of those second date questions to ask her or him; it can help you be imaginative while also learning a lot about the other person.

If they talk about how they wish they could quit their job at Microsoft to become a full-time chef, you’ve definitely unlocked another layer of information about this new person. It will help you build a deeper connection, even if it does not say too much about their concrete future plans.

Related Reading: 10 Thought-Provoking Relationship Check-In Questions for Deeper Connection

25. What were you like in high school?

If you’re running out of things to talk about on second date, then go for this one because it works like a charm and will make sure you two have lots to chat about for a while.

Are you out on a date with someone who was a jock? You can now segue into discussing various sports teams. Or if they say they were into public speaking and drama in high school, this is a great way for you to plan a date where you both go out to watch a play. Seize the opportunity and get that third date!

26. Have you told your friends about us?

Now, you have to position this question very softly so they don’t think you’re being too ambitious about this connection. Things are still new, so you can only dip your feet in the water, and not dive in any time soon. Even if you are indeed looking for a serious relationship with this person, don’t come off as very eager. Ask them casually if they usually discuss their dates with their friends, and it may just open a can of worms about some dating stories from their past.

27. What is the craziest thing you have ever done?

Maybe it was skinny dipping, bungee jumping, or shoplifting — This way you’ll know if you’re into someone who is experimental, adventurous, or just a bit of a kleptomaniac. Discussing crazy stories like these can actually help people feel more at ease in each other’s presence.

Related Reading: Waiters Share Five Of The Worst First Date Stories They’ve Seen

28. What does your ideal day look like?

What to ask on a second date to get to know somebody better? Ask them what their favorite day looks like. Do they want to start their day with an affogato and end it with a glass of wine? Or would they rather sleep in all day, and wake up at 4 p.m. to go for a calming walk? This is a fun, imaginative question for second dates that will ensure that there is no awkward silence between the two of you.

29. Do you believe in astrology?

This is one of the things to ask on second date to understand more about the core of this person. Are they someone who takes charge of their destiny, or are they more easygoing and prefer things to be left to the Universe? Without passing any judgement, use this question to gauge how your date goes about their life, and ask them about other religious beliefs as well.

Some people read their horoscope before they apply for a job, while others are constantly preoccupied with making things happen in the way they want. Either way, this can give you a lot of information about who your date is, and whether the two of you can be in a happy relationship and stay on the same page regarding this.

30. Do you have any weird talents?

One of the more funny questions to ask on a second date, use this one when you are sensing a lull in the conversation. And if you yourself have a weird talent, now is the time to go all out and embarrass yourself. Just don’t lose track of where you’re sitting as you try to touch your nose with your tongue in the middle of an elegant restaurant.

31. What do you think of PDA?

PDA refers to public displays of affection, which usually translates to kissing, hugging, or holding hands in public. Everyone has a different idea of how openly they want to show affection to their partners in public. That is why, this is one of the second date questions to ask a woman or a man you are physically attracted to.

This way, you know how or when to initiate consensual physical touch. If they don’t like being touched at all in public, you now know not to lean in for a kiss in the middle of the park.

32. Which cause do you feel the closest to?

If you’re running out of things to talk about on second date, time to steer away from questions about personal life to something more political. Everyone has a cause they support and for some, it might just be Taylor Swift’s music. This is one of the most crucial second date questions to ask him or her to really dive deep into what bothers them.

Some are very passionate about queer rights, while others are focused on global concerns of fascism. So what does your date really care about?

Related Reading: Transparency In Relationships: Meaning, How To Show & Some Secret Tips

33. Ask them to list their favorite restaurants

What to ask on a second date when your date isn’t really opening up to you? Some people just take a while to talk about themselves and may not always give you intimate details from their lives or openly discuss their past experiences. In this case, you need to graze around topics that are more general.

To make small talk on second dates, ask them to list some of their favorite restaurants in the city. This way, you have an idea of how often they like to go out, what they like to eat, and what is perhaps an interesting place for you to try. If they don’t feel rushed, and feel safe with you, then hopefully on the third date, they’ll do more than talk about food with you.

34. Tell me your current state in life, in three words

One of the things to ask on second date is asking the person you’re out with to describe their life in three words. These words do not have to add up to a full sentence and can just be random. For example, words like ‘happy,’ ‘thriving,’ ‘confused,’ or ‘lost’ count. This can help you understand whether you two are on the same page in life.

35. What was your favorite moment from our first date?

It’s a good compatibility question for a couple. Here’s hoping they don’t say, “Remember when you dropped noodles on your shirt because the ramen was too hot?” Or here’s hoping they do, because that’s not embarrassing at all, and could actually be one of the sweet moments that they remember so fondly.

This is one of the cutest second date questions to ask a woman or a man you are interested in. Get to know whether your previous meeting was a good date for them, and what kind of first impression you’ve made.

36. What is your happy place?

To end this list of things to talk about on second date, let’s go with a warm and endearing question. What is the one place that your date loves being at? It could be the lake close to their place or it could be their mom’s basement because that’s where they spent all their time as a child. Either way, this is a nice way to get to know your date better and what lights up their life.

This checklist of second date topics is a pretty broad guide and is much better than just asking someone their favorite color. You don’t have to use them all or in a particular sequence. Just juggle a few that fit your context, let the conversation build up organically from there on, and most importantly, give your date a chance to talk, respond, and ask questions of their own. Here’s to no awkward pauses!


1. What should I talk about on a second date?

The second date is the perfect opportunity to get to know the other person truly well. So, build upon the things you already know about them. You can also talk about families, past relationships, and life goals, as most people do.

2. How do you make a second date interesting?

You can talk about hobbies and passions, swap stories about funny or happy moments, and flirt a little to make a second date interesting.

3. Should you kiss on a second date?

If both you and your date are feeling it, there’s no reason you can’t or shouldn’t. In fact, a kiss on the second date can be considered a promise that this thing will lead somewhere.

4. How many dates until you are dating?

Well, typically, most people follow the 10-date rule. This means if you have been on 10 dates, you’re an item.

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