Skip to Content

36 Interesting Questions to Ask on a Second Date

In today’s post we are going to cover 36 interesting questions for a second date.

Congratulations! You’ve managed to survive the awkward first date. Not only did you survive it, but the other person is interested enough to agree to a second date with you. Second dates may have a little less uncertainty than first dates but make no mistake — the awkwardness hasn’t left the building yet. 

In fact, second dates come with added pressure. They didn’t lose interest on the first date, but will you keep their interest beyond the second one? 

36 Great Second Date Questions 

A research study published by the Society for Personality and Social Psychology found that intimacy could be cultivated between strangers by asking and answering 36 questions.

If you’re heading into a second date and need questions to ask, this study offers many that can help you get to know each other better. It’s even possible that it could lead to love. 

Here are the 36 questions asked in the study that help build intimacy. If your partner is willing, you could even suggest that the two of you work through the whole list together.

It could be an interesting way to get to know each other without either of you having to come up with topics of conversation. You could even use this as a backup plan if the conversation doesn’t naturally flow.

Just don’t treat it like an interview. Suggest it as a game. Also, if you don’t think they’re up for it, you could simply borrow some questions from the following list. 

Try these ice breakers to warm up

1. Given the choice of anyone in the world, who would you want as a dinner guest?

2. Would you like to be famous? In what way?

3. Before making a phone call, do you ever rehearse what you are going to say? Why?

4. What would constitute a “perfect” day for you?

5. When did you last sing to yourself? To someone else?

6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?

7. Do you have a secret hunch about how you will die?

8. Name three things you and your partner appear to have in common.

9. For what in your life do you feel most grateful?

10. If you could change anything about the way you were raised, what would it be?

11. Take four minutes and tell your partner your life story in as much detail as possible.

12. If you could wake up tomorrow having gained any one quality or ability, what would it be?

13. If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?

14. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?

15. What is the greatest accomplishment of your life?

16. What do you value most in a friendship?

17. What is your most treasured memory?

18. What is your most terrible memory?

Some deeper questions

19. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?

20. What does friendship mean to you?

21. What roles do love and affection play in your life?

22. Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.

23. How close and warm is your family? Do you feel your childhood was happier than most other people’s?

24. How do you feel about your relationship with your mother?

25. Make three true “we” statements each. For instance, “We are both in this room feeling…”

26. Complete this sentence: “I wish I had someone with whom I could share…”

27. If you were going to become a close friend with your partner, please share what would be important for them to know.

28. Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.

29. Share with your partner an embarrassing moment in your life.

30. When did you last cry in front of another person? By yourself? (This is a great question for a second date, as it helps you connect with your partner on a deeper level).

Try these conversation starters to make the conversation more interesting

31. Tell your partner something that you like about them [already].

32. What, if anything, is too serious to be joked about?

33. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone?

34. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be?

35. Of all the people in your family, whose death would you find most disturbing? Why?

36. Share a personal problem and ask your partner’s advice on how they might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.

This isn’t meant to be a long, in-depth interview. Keep your answers as brief as you like, and if you can’t think of an answer, just keep it moving.

Also, you can even abandon the list entirely if one of these questions sparks natural conversation. 

Interesting questions to ask on a second date pin

How to Ace the Second Date

Keep in mind that there’s no way to guarantee that another person will see you as a good match. That’s just not realistic.

But there are some things you can do that will help them see you as a good date, even if you don’t make a good match.

Be Kind

Kindness matters more than you think. Even if you’re not compatible, you can still make sure that you’re treating the other person with respect and consideration.

You can be kind even when you’re being rejected.  

Be Your True Self, Not Your Best One

Show up as the most authentic version of yourself, not your aspirational self. You might want to put the best foot forward, and that’s admirable. That best foot should still be honest.

Don’t hide flaws or pretend you’re different than you are. No one wants to have the bait and switch routine pulled on them. Just be yourself. 

Make an Effort

Come up with a cool date idea. Also, if you’ve decided on dinner, find an interesting place to go. If you’ve decided on an activity, pick something fun. Make an effort with your appearance but also with your planning.

Keep It Light

Don’t bring so much pressure to your dates. You can’t force connection — not even with this list. Instead of interviewing the other person as a potential soulmate or life partner, just consider relaxing and letting things develop organically.

Be genuinely curious about who they are. Share who you are. Don’t think you have to tell them everything and learn everything in the space of a date or two.

Leave Expectations at Home

Don’t assume how the date will go. Also, keep in mind that if you choose to pay, you’re not owed anything for doing so. Split the bill if paying makes you think you’re entitled to physical intimacy. Leave your expectations at home and just try to have fun. 

Be Honest

It’s really important to be honest about who you are and what you want. So, don’t try to tell other people what they want to hear. And be clear about the relationship you want so that your date can make informed decisions about dating you.

Don’t Unload Your Baggage

Second dates aren’t for dumping your baggage on the table and complaining about your exes. Also, it’s not attractive to spend an entire date complaining – you can be honest without unloading your baggage on your unsuspecting date. 

Dating is more of an art than a science. Sure, you can follow a few basic rules — otherwise known as common courtesy. But you can’t force a connection. What you can do is make sure that you show up as a good date.

The 36 questions may not end in a match with the love of your life — but it could.

And it’s certainly a good ice breaker for those awkward moments on a second date. If nothing else, you could learn a lot about each other and maybe even make a friend.

Recommended reads:

The Truly Charming