21 Questions To Ask On A Second Date

August 1, 2023 |
Updated On: August 1, 2023
questions to ask on a second date
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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.

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.

21 Questions To Ask On A Second Date And Why

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, in short, you won’t be stiff as a stick this time around.

Panicking about what to do to keep a second date interesting 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 what to do and not do 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 21 on-point questions to ask on a second date, you will never have a tongue-tied moment or find yourself filibustering:

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)?

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 your flirting skills. Flirting too soon into the date might just mean you’re eating dessert alone.

3. How did your love for dogs start?

questions to ask on a date
Build upon something you already know about your 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. Even if s/he’s a cat lover and you’re somehow trying to make it work, ask them about where that originated from. 2nd date questions don’t have to be rocket science, you know.

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. In turn, 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.

It can turn out to be one of the thought-provoking questions to ask on a date. Chances are your date may not have given any real thought to the underlying reasons for their choice. This 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 their 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’d you narrate your life journey in under 2 mins?

Want a quick recap of your date’s life? Ask them to narrate their life journey to you in under 2 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.

Besides, 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, you’ll have something to talk about on the third date!

7. What is your life plan for the next 5 years?

This becomes one of the most important questions to ask when starting a relationship. 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.

This is also a smart way to put 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?

Among the mildly flirty questions to ask on a second date, this one will surely elicit praise and compliments for you. So, gear up to revel in some moments of flattery. 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 amount of giving out compliments, though. If you give too many, you may just come off as too…eager. On the other hand, too few compliments will make you seem like you couldn’t care less. Perhaps it’s not all about questions to ask on a second date, think about what your answers will sound like too.

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.

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 relationships’ territory. This is one of the past relationship questions to ask on a second date you can lead with. Asking someone about their worst heartbreak 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?

Yet, another one of those crucial questions to ask when starting a relationship. The idea here is not to see where the blame for a past relationship not working out rests. But to assess how your date feels about it now.

If they’ve healed and truly moved on, 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, you need 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 relationship queries qualify as acceptable questions to ask on 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?

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 ask on a second date if you want to explore the possibility of a future with this person. Love, romance, trust, respect – what is it that they value the most? And does it align with your relationship expectations?

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

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

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

In case all the relationship and future talk start 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 spirit, and the energy of your date, even more. When you’re thinking about how to keep a second date interesting, 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.

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

Letting a dream job slide, missing that coveted college admission by a whisker, 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 what you missed out on yourself.

When you’re thinking about what to talk about on a second date, think about open-ended questions like these that develop further conversation smoothly. Asking your date about 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 awful dates. You could swap stories and share some hearty laughs to keep a second date interesting.

18. Who is your favorite person in the family?

Make this one of the questions to ask on a second date if you’re genuinely interested in the person. One’s family is a huge influence on one’s personality. This question opens the door to more interesting discussions about family 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?

This question 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? Is there a rule about when they kiss, sleep with or have a sleepover with a potential partner? You can set some unspoken ground rules of dating by asking this question and manage your expectations better, going forward.

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

Tricky as it may sound, do add this to your list of must-ask 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.

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. 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.

This checklist of questions to ask on a second date is a broad guide. 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. Whenever you hit an awkward pause, you can always pull a few news ones from your sleeve.


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.

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?

Yes, if both you and your date are feeling it, there’s no reason why you can’t or shouldn’t. In fact, a kiss on the second date can be considered as 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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