35 Interesting Questions To Ask On A Second Date

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After a successful first meeting, you may be excited about the next date. Planning your second date questions can help you have a successful date. During the first date, things are new and exciting, and couples try to get to know one another through conversations and activities. However, to explore more about each other, it is important to plan your second date with the same level of excitement and curiosity.

So, if you are pondering over what to talk about or how personal you should get on your second date, this post may help you sort that out. Read on to know what questions to ask on a second date and how you can keep the conversation flowing.

35 Questions To Ask On A Second Date

Here are a few questions that you can ask your crush on the second date. These will help you avoid awkward silences and give you a deeper insight into your date’s personality.

1. What made you decide to agree to a second date?

Ask them what made them decide to agree to a second date

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While this is a loaded question, it’s good to know what motivated them to explore your connection further. It will tell you what they liked about you and might help you in your future dates. Your ego will also get a boost after hearing all the good things.

2. What is your favorite moment from our first date?

This is a great conversation starter if your first date went well. It will take you back to that wonderful day and remind you of the sweet moments you shared. Some funny moments might come up in the conversation, leaving you in splits again and helping you relax around each other.

Quick tip
Even if you think your wavelength matches your date after a second date, don’t propose as yet, as it is too soon to make serious commitments.


3. Who are you closest to in your family?

Delving into family matters might seem too personal on the first date but is fine on the second date. This question will give you a glimpse into their family dynamics and the importance of family in their life. It could also lead you both into a discussion about family values and help you assess if theirs align with yours.

4. What do you generally do in your free time?

Asking about your date’s activities in their free time will give you more insight into them as a person. This information might also help you plan future dates around something they enjoy. For instance, if they enjoy watching action movies, you can take them out for a movie or plan a movie marathon.

5. Do you enjoy your work?

Knowing about someone’s work-life can tell you a great deal about the person. It will tell you what your date prefers doing in life and if they are in the right professional field. If they are unhappy professionally, the distress can spill over in the other aspects of their life.

6. What are your dreams?

Asking about your date’s dreams will tell you what drives them to keep going. Their dreams shape their life. If their goals in life are entirely different from yours, you might find it difficult to adjust to them.

7. What do you fear the most?

Expressing your fears in front of someone makes you quite vulnerable. Hence, if your date shares such an intimate detail with you, it is a positive sign that they are very comfortable with you. By exchanging your worst fears, you can connect on a deeper level.

8. What was your first impression of me?

This question will give you an idea about the general impression you make on dates. It can also offer a perfect opportunity to refute any misconceptions and make some changes in how you present yourself if the perception was unfavorable. You two can have a light-hearted conversation around the topic and laugh it off if you both were completely off the mark about each other.

9. What is your funniest first-date experience?

Relating funny first date experiences will make your date more relaxed and give a lively touch to the conversation. You can go ahead and share your stories of disastrous dates and laugh about it for hours.

10. How long have you lived in this city, and what do you love about it?

You can get a bit of your date’s background by asking this question. You can also ask follow-up questions to know where they are from, the purpose of moving to the city, the things they love about the city, and their motivation to stay. If they are new to the city, you can offer to show them around and explore the hot spots together.

11. What do you expect from a relationship?

This question will help you figure out if you are on the same page regarding relationship goals. If you are looking for a serious relationship, but your date wants a casual relationship, there is no point in taking this forward.

Point to consider
Just because they showed interest in meeting you again, don’t probe into their personal life. Especially refrain from asking questions about their exes, other people they are seeing, and flings.

12. What interests you the most about me?

Ask them what they find most interesting about you

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If you are keen to know what your date thinks about you, ask them this question. You will be able to understand the things about you that attracted them. It is an excellent way to know if your date is into only your looks or finds your personality appealing.

13. Which is your favorite travel destination?

Travel is generally a topic that usually gets the conversation flowing. You can talk about the destinations you have been to and your fun travel experiences. Knowing your date’s favorite travel destination can also help you figure out if you share any travel preferences.

14. Do you consider yourself religious?

If a person is religious, it can have a significant impact on their behavior. So, if you are planning on taking things forward with your date, you should know the importance of religion in their life. If one of you is religious and the other is not, the relationship will need certain adjustments from both sides.

15. Do you have any pets?

If either of you has pets, they will become an integral part of both your lives once you start dating seriously. If they don’t have any pets and do not like them, while you have a pet, it can be a reason for major discord between you. On the other hand, if you both love pets, you can ask whether they are a dog or a cat person. Exchange pet stories and connect over your shared love.

16. What are you really grateful for in your life?

Asking this question will help you figure out if your date takes everything in life for granted or are genuinely grateful about something. It will help you gain a deeper insight into their personality and life.

17. Why didn’t your previous relationship work out? When did it end?

It is crucial to understand how your date feels about their previous relationship. Have they completely moved on, or are there any residual feelings? Any lingering emotions might have an impact on your relationship with them. Also, if their last relationship ended recently, it is good to proceed with caution as you might be their rebound.

18. If you were given an option to choose a superpower, what would it be and why?

Discussing a lighter topic, such as superpower, will make the discussion more interesting and exciting. It will encourage your date to use their imagination and give them a chance to express their fantasies. The answers might reveal a hidden side to their personality that you haven’t seen before.

19. Do you smoke/drink?

Habits such as smoking and drinking have a significant bearing on one’s life. If smoking or drinking is a deal-breaker for you, clearing things beforehand is a good idea.

20. How would you describe yourself in three words?

This question will help you understand how they perceive themselves. You can get a more in-depth idea about their personality by having a detailed discussion about the three descriptors. Talking about yourself using three words in response will keep the conversation lively and wouldn’t seem like an interview to your partner.

21. Which was the last movie you watched that had a huge impact on you?

Movie-related topics generally make the conversation longer and livelier. Asking your date about the movie that impacted them the most will tell you their film preferences and how they perceive things. You will uncover another aspect of their personality by understanding if they watch a film for entertainment and forget about it or if movies have a lasting impact on them.

22. Do you have any quirky habits?

Ask this question to know your date better and build a deeper connection. While this is quite a personal question, you can start by telling your own weird traits. Quirky traits can be anything, from being finicky about cleanliness to hating the mere sight of milk.

23. What qualities do you seek in a potential partner?

This question will tell you the qualities your date is looking for in a potential partner and how you fit the criteria. If you do not match their criteria, or if the qualities they are looking for are completely different compared to yours, it might create some friction in the long run. For instance, if they seek someone who is career-oriented and driven to make money, and you are not that person, the relationship might not work out.

24. What food item can you never get enough of?

Ask them about their food preferences

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It is a good light-hearted question to ask if the conversation is getting too heavy. You will get to know your date’s comfort food item. This information will also come in handy while planning the next date.

25. Where did you spend your childhood?

You can have an engaging discussion about your date’s childhood. Asking this innocent question will open doors to more detailed questions about their childhood. You can ask about their school days, childhood friends, and favorite childhood memories.

26. Is there anything in your life you would want to go back and change?

By asking this to your date, you would know if they regret anything in their lives. Talking about regrets in life might reveal many new things about them that they might not usually share. This discussion would also help you know how content the person is with their current life.

27. What is the craziest thing you’ve ever done?

Ask them about the craziest thing they have ever done

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This question is a perfect invitation for all kinds of fun stories. It will reveal their adventurous side and create a playful environment. Exchanging crazy stories will inject a dose of laughter into the conversation and will bring you two closer.

28. What do you find sexy in a person?

Ask this question after you two have become comfortable with each other. It will give you insight into what characteristics your date perceives as sexy — is it the looks, personality, or attitude of a person? Turn up the heat by using this question to flirt playfully with them.

29. Is there something about yourself that you wish to improve?

A person grows when they accept their flaws and work on them. This question will reveal if your date is someone who wants to be a better person. If your date thinks they are already perfect, they might be lying to impress you or think they are God’s gift to humankind.

30. Have you been in any long-term relationships?

By asking this question, you will know a few details of your date’s relationship history as well as their definition of “long-term.” If your date has been in a series of short-term relationships, it may be due to sheer bad luck or could be perceived as a red flag. While you should give your date the benefit of the doubt, tread carefully if you are looking for a long-lasting relationship.

31. Do you follow any dating rules?

Knowing if your date follows any dating rules will tell you what to expect from them during the first few dates. You will know the level of intimacy they are generally comfortable with, the wait time before the next date, and the behavior they expect from their partner. These pieces of information will help you understand if your expectations match and give you an idea about your next move.

32. What is the one thing you are really good at?

On a second date, you want to know more about the personality of your partner. The answer to this question can offer a deeper insight into their character based on how they talk about their strengths. Do they seem confident? Are they humble or arrogant?

33. What things do you feel we have in common?

Discussing the things you have in common can help you understand how well you gel with each other. This can make you more comfortable with each other and help in building a stronger bond. It allows you to figure out if your date has the right idea about you and rectify any incorrect notions.

34. Which is your most joyous memory?

Ask them about their happiest memory

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If the conversation is getting too serious, a question like this will lift your mood. Your date will feel happier and more relaxed as they recollect their favorite memory. It is a great way to find out what makes your date happy — is it something purely materialistic, spiritual, or sentimental?

35. What is a deal-breaker for you in a relationship?

Every relationship requires some sacrifices and adjustments, but everyone has certain aspects that they can never compromise. It might be controlling behavior, infidelity, political inclinations, or even food preferences. You both need to know these things about each other to decide the future of the relationship.

Frequently Asked Questions

1. What does a second date mean to a guy?

If a guy wants to ask you out for a second date or shows interest in meeting you again, there are chances he is mighty impressed with you, finds you attractive, and wants to know more about you. He may be enjoying your company or liking the chemistry between you and him. Don’t jump to conclusions yet; take it slow.

2. Should we text between the first and second dates?

Yes, and often, if you see a spark between you both. Texting after your first date, if it is good, can indicate to the other person that you are interested in learning more about them. Do not spam but sending a couple of text messages to express how you loved spending time with them or appreciating their efforts can go a long way in impressing them.

You may ask some or all of these second date questions if they are not making your date uncomfortable. Questions about their favorite travel destination or food can give you an insight into their preferences. Ask about their dreams and goals to know about their aspirations. Use fun questions or relate a funny incident if the mood gets serious. Try to learn about their expectations from a partner to gauge compatibility parameters. Share childhood memories and quirky habits, but make sure you have a lot of fun and not an interview.

Infographic: Signs You Should Go On A Second Date

Sometimes we click with people in the first meeting itself, while other times, it requires more talking and meeting to know and like them. So whether it’s you or your date proposing a second date, here are a few signs and hints that can help you decide when going on the second meeting may be a good idea.

when can going on a second date be a good idea [infographic]
Illustration: MomJunction Design Team

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