The 25 Top Questions To Ask On A Second Date

The second date is scheduled and you’re excited — or maybe still a bit anxious. 

You may feel like you have exhausted your conversation ideas on the first date, but that's simply not true. You just need to be willing to go a little deeper. 

Second-date topics of conversation allow you to explore each other's personalities a little more. 

You have wider options for what to talk about on a second date because you can move out of the “safe zone” that people tend to stay in on first dates.

What's in this post:

What should happen on the second date?

Your level of nervousness should be less acute on the second date. You have already succeeded to some extent by getting the second date in the first place, so give yourself permission to relax. 

Both people on a second date are hoping to learn more about each other and maybe spark some chemistry.

A second date should have one or more of the following:

Spontaneous laughter

Some flirting

Going for a walk after lunch or dinner

More time spent together than first date

Deeper conversation


Maybe kissing

Of course, a date should not feel like you have to complete a checklist. People are variable.

Things can move forward quickly for some couples while others need more time to reckon with their feelings for each other. 

When you ask yourself, “How should I prepare for a second date?” focus on planning an activity and encouraging interesting conversations.

You and your date are still very much in the talking phase, especially if you're hoping to nurture a long-term relationship. 

You can definitely expand second-date conversation beyond shallow first-date topics like “What's your job like?” or “Where did you go to school?” The time has come to draw out information that can reveal useful insights about whether your date might ever move up to significant other status.

25 Essential Second Date Questions

1. What is your happiest childhood memory?

This should be a comfortable subject for both people. Even someone who had a tough childhood probably has a nice memory that stands out. 

The question could give you a glimpse into the person's formative years and help you know what makes the person happy. The response could be important depending on what is revealed. 

couple drinking wine at dinner questions to ask on a second date

If your date mentions that childhood was difficult, then this indicates a willingness to show vulnerability by admitting that not everything is perfect in his or her background. 

Difficult circumstances, however, could produce results that go in opposite directions. Tough times can make someone empathetic or insensitive.

2. Who are you closest to in your family?

Asking this question gives you an opportunity to probe into your date's personal relationships. You could find out that the person has a close and loving relationship with his or her family, which could be a good sign. 

Such an answer may indicate that the person is willing to put in the effort to cultivate strong relationships and does not take close connections for granted. 

Any information about your date's family will also provide clues about his or her character. Our families strongly influence us whether we turn out like our relatives or not.

3. Why did you move here (or stay in your hometown)?

You may have touched on this during the first date, but, if not, you can delve into the subject. Moving to a new town to pursue education or career opportunities may show ambition. 

However, a negative event might have prompted the move. 

If your date has an answer of this nature, you could gain greater insights about his or her history. Also, the desire to try something new is a sign that the person might have a problem-solving nature. 

When someone chooses to stay in a hometown, resist the urge to judge that decision negatively. The person might have had responsibilities that could not be abandoned, and some people like where they grew up and want to contribute to their community.

4. What was the worst job you ever had?

Who doesn't like to complain about work? This is a good icebreaker question if you suddenly are unsure what to say next. The answer might show how the person deals with adversity or difficult people. 

You could learn how long it takes your date to become fed up with a situation too. Some people are quick to bolt when things go wrong, whereas others will persist through abusive circumstances. Whatever the answer, it will probably be very interesting.

5. Have you ever been bullied?

Use this question as an invitation for your date to trust you. Some victims of bullies are quite scarred by their experiences, and they could be reluctant to provide details. 

Don't push for an answer if the question seems to cause too much distress. Most people, however, may have a bully story to relate that was not terribly traumatizing. In most cases, your date's answer introduces an opportunity for you to show your caring and sympathetic side.

6. If you had $1 million to give to charity, what type of cause would you support?

Almost any “If you had $1 million…” type question promotes a fun conversation. Most of us enjoy fantasizing about what we would do if we were wealthy. 

When you combine this with the concept of charitable giving, you could draw out information about what the person thinks is important. The answer should inform you about the causes or problems that matter to your date. 

Of course, if someone hates the idea of being philanthropic on that level, you could have found a red flag about extreme selfishness.

7. What activity makes you lose track of time?

A truly engaging activity can make a person enter a flow state where the concept of time slips away. What makes someone enter a flow state really varies. It could be athletics, writing, math, woodworking, painting, or something else. 

What matters is that it consumes someone's attention to the point that the world drops away. People who have a passion like this, even if it's a quiet hobby, have the ability to feel content with themselves and focus on their goals.

8. Tell me about your pet peeves?

Even people who are not prone to complaining will do so if directly asked. During your second date, both of you should recognize that the question is mostly for the sake of fun. You could learn about quirky things that annoy the person. 

Small details about what gets under someone's skin can be endearing and also clue you in about something you should avoid doing unless you want to upset your date. 

On the hand, someone who has many pet peeves might be a hard-to-please personality who is always looking for fault.

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9. What is your dream job?

First dates are when we talk about the jobs that we have, but now the time has come to discuss what would be ideal. Your date might realize that his or her dream job is not realistic but talking about it can be a pleasure. 

couple laughing together questions to ask on a second date

The answer could show the desire to learn a new skill, help people, restore the environment, or make lots of money. Someone whose dream job is not having any career at all could be someone who wants to focus on home and family, which might be what you're looking for — or not.

10. What do you think that we have in common?

This could serve as a subtle test to see if your date remembered some of the things that you talked about on your first date. You'll find out just how much the person has been paying attention to you. 

Your date's response could show whether he or she has interpreted your characteristics correctly or is making mistaken assumptions about your likes and dislikes. 

You could also learn more about each other as you compare notes about why you could be good matches for each other.

11. Is there something in your past that you regret?

The answer that you get could be huge or just interesting. Everyone has regrets, and discussing them opens up the possibility of talking about any life lessons that the experience imparted to the person. 

A question like this also presents a chance to gauge your date's willingness to talk about uncomfortable subjects. Many people try too hard to present themselves as perfect to dating partners, but the subject of regrets demands honesty and vulnerability.

12. Can you tell me about something that you're very proud of?

Some people like to gush about their accomplishments, but other people might tend to be more humble. Neither extreme is wrong but will give more clues about your date's personality

By asking this question, you give a humble person permission to brag a little. You might even find out something truly impressive about someone. 

Overall, what someone claims to take pride in provides hints about what he or she values and considers worthwhile.

13. What is your favorite thing to do when you're by yourself?

This might seem like a strange question for someone who is actively interested in spending time with you, but how someone approaches solitude can be very informative. 

Some people have trouble occupying their own time without outside direction. This is not necessarily bad but a sign that the person likely craves company frequently. Such a person might be an extrovert

An introvert, however, will likely have many answers to this question because he or she enjoys solitary activities and finds them renewing.

14. If you had to enter witness protection, what would you miss most about your current life?

This question can be fun while helping you learn what your date values in the here and now. The thought of giving up an identity and community will naturally distress most people, but talking about it could reveal what someone would do if given a fresh start. 

Your inquiry could even spark a playful discussion where you imagine what crime the person witnessed that required going into hiding.

15. If your house was on fire, what three things would you want to save?

Here's a question that forces your date to rank material possessions. You could learn how connected someone is to material things or items with sentimental value. 

A person's practical nature can come through too if he or she wants to save important papers like a birth certificate. Most people might say that they want to grab family photographs, which is a good clue that a person values family and relationships. 

This question can tease out traits like indecisiveness or preparedness.

16. Have you ever done anything to step out of your comfort zone? How did it go?

In practice, expanding horizons can be a challenging feat full of obstacles. Some people never work up the nerve to step outside their comfort zones. So asking this question will reveal their appetite for risk and trying new things. 

Consider if their approach matches yours. Is it an important quality for you? Or maybe you're the one who could use a tempering force in your semi-reckless life? You know what you need.

17. What's the most interesting thing you've learned recently?

A twist on a common question, framing it in the present or recent past is clever and hits the perfect tonal note for a second date. It's not too pushy while simultaneously being a bit more substantial than the average getting-to-know-you query.

Right now, you're casually enjoying each other's company and keeping an eye out for relationship potential. But you're not yet at the life-sharing point. This question serves the mood by being both light and probing. 

18. Do you have any travel plans coming up?

A person's travel history and hopes reveal a lot about their tastes, interests, and approach to life. Do they prefer to stay close to home? Are they fearful of planes, trains, or boats? Or are they interested in exploring the world up close?

If you're an extensive traveler, try not to judge if they don't have any big trips on the horizon. The economy is precarious, and post-pandemic realities are still impacting flight and hotel prices.

If they're heading somewhere interesting soon, ask more detailed questions about their itinerary to keep the conversation alive.

19. What's something you've wanted to try but haven't had the chance yet?

People aren't their pasts; present and future goals and dreams also shape personalities. This question will provide insight into who they want to become.

Does their answer align with your hopes and aspirations? Do you find their aims interesting, exciting, or inspiring? To avoid a lull in the conversation, latch onto details to expand the questioning.

20. What's your favorite way to relax after a long day?

Downtime routines are personality windows. Is your date the kind of person who doesn't understand the concepts of “doing nothing” and “relaxing?” Or do they have a deep appreciation for hyper-comfort lounging?

If, like millions of people worldwide, they spend a few hours vegging out in front of a screen daily, expand the line of questioning by asking about their favorite shows.

21. What's a skill or talent that you've always wanted to learn?

Get a peek at your date’s deep-seated passions through this question. The answer could reveal another side of their personality.

Be suspicious of people with a stock answer crafted to make them seem much more exciting or edgy than they actually are. If your date says something outrageous, sprinkle them with follow-up questions. If they fumble, they're probably faking the funk.

22. What's your favorite book or movie of all time?

You could argue this is an unfair question — because who can pick just one!? But if your date doesn't hesitate to answer and can name a single favorite book or movie, pay attention.

Why? If their chips are all in on one option, their choice probably reveals a lot about who they are and how they think.

23. What's the most spontaneous thing you've ever done?

Many people’s “most spontaneous” life moment usually involves something stupid. So don't expect the real answer off the bat. After all, it's only the second date, which is still very early. 

But don't worry; if the relationship stands the test of time, you'll get the real dirt in time.

In the meantime, make note of the answer. It could expose some red or green flags.

24. If you could have any superpower, what would it be?

Everyone wishes for superhuman abilities that would render life considerably more manageable. Imagine if you could stop time, fly, or read people's minds!?

This is an excellent second-date question because it's lighthearted yet could reveal how your blossoming admirer navigates their days and what they prioritize.

Don't forget to follow up with a “why?” 

25. What's the best concert or live performance you've ever been to?

Asking about music and concerts is relatively standard, but it's a safe query to fill awkward silences that may elbow their way into the conversation.

Hopefully, you'll discover a few shared favorites that will give flight to an engaging discussion.

Remember to flip the query on its side and ask about the worst show they've ever been to.

couple laughing and talking second date questions

Should I kiss her on the second date?

Now we have arrived at the question that looms large over most second dates. The concern of whether to kiss or not kiss depends on the people.

If you're feeling attraction and receiving body language clues that invite contact, then the time to kiss may be at hand. Body language can indicate desire for a kiss in many ways. 

If she leans toward you, touches you at all, has flared nostrils, or tilts her head while looking at you, then she could want contact.

Ultimately, the decision to kiss has to be made on a case-by-case basis. The kiss should come at the end of the date and hopefully set up excitement for a third date

During the course of the second date, you should get better insights into her interest in taking things to a physical level. You could start by holding her hand, touching her cheek, placing a hand on the small of her back, and then judging her reaction. If she does not pull away, go ahead and kiss her.

Remember to Have Fun with Second Date Questions

Both of you are going into this second date with high hopes. The pressure to impress might interfere with acting like yourself, but you need to come through as your authentic self. 

Revving up the confidence to ask someone out on a date might involve some level of faking it till you make it, but the feelings and attraction need to be genuine. 

Use the top questions to ask on a second date to help both of you relax into conversation and learn more about each other. Meaningful conversation will improve your ability to feel accepted.