Best Questions to Ask on a First Date

Asking the right questions can make your first date with someone amazing. These are some of the best questions to ask on a first date that will give you and your partner an idea of what kind of person they are, as well as being fun!

The “spicy questions to ask on a first date” are questions that can be asked during a first date. They can be used to make the conversation more interesting, and will also help avoid awkward conversations.

It’s a bit nerve-wracking to strike up a conversation with anybody — you’re on an improv stage for two, and you have to think of things to say on the run, avoid uncomfortable silences, and come off as at least reasonably charming.

On a first date, small conversation may be particularly nerve-wracking. While it goes unstated, you’re being judged on your appearance (both in personality and looks). It’s similar to a “job” interview for a possible significant other. It might be the start of a lifetime love affair if you succeed. If you blow it, you could never see that particular someone again.

Isn’t there any pressure?

There are lots of lists out there that offer effective things to ask someone on a first date to help you succeed at this type of high-stakes small chat.

Basic, stock questions (“Where are you from?” “What do you do for fun?”) and more creative, out-there questions (“If you could only bring three items with you on a desert island, what would they be?”) tend to dominate these lists.

The trouble with the first set of questions is that they’re tedious; if you’re dating a lot, you’ll become weary of being asked how many siblings you have and whether you enjoy your work. The trouble with the second group is that if you simply throw them into a discussion, they might come out as a little random — and too contrived.

Thankfully, it doesn’t have to be a binary choice. There’s a better approach to ask first date questions that combines the two sorts of queries.

You do ask the standard, stock questions; familiar as they are, they establish a soothing routine that relaxes individuals. You, on the other hand, utilize them as starting off points for more fascinating queries.

This method finds a wonderful balance between seeming to be trying too hard and appearing to be trying too hard.

You ask a common stock question, then act as though your date’s reaction prompted you to think of another semi-related, more original topic. Of course, you already knew the answer, and that’s OK. The paradox of charm is that in order to seem natural, you must be well-prepared; it’s not that people don’t realize your repertoire is partly “written,” but if you execute it smoothly and engagingly enough, they don’t mind and love riding along for the trip.

With the Standard-Question Interesting-Follow-Up Method, you can ask better first date questions. 

The benefit of the standard-question interesting-follow-up technique is that it will lead your first date talks to areas where you’ll learn a lot about the other person without having to ask them, “What is your darkest fear?” directly — and uncomfortably. or “In five years, where do you see yourself?”

While your questions should provoke thinking, your partner should be able to respond quickly; people feel stupid when they have to do the “Hmmm, hmm, well, oooh, that’s a difficult one” thing and struggle to come up with a solution. Simply asking yourself the question and seeing whether you like thinking about it and can picture how you’d react is an excellent way to assess if a question reaches the sweet spot.


Also, keep in mind that a discussion isn’t the same as an interrogation; you don’t want to keep asking questions without giving any information about yourself. Your date will, presumably, turn the tables on you and ask you questions of their own. If they don’t, add some personal comments; studies suggest that persons who share more about themselves (while remaining within proper boundaries) are appreciated more than those who are more guarded. Of course, if your date is a talkative narcissist, it’s probably a bad sign.

Finally, although the follow-up question does not have to be identical to the standard inquiry you asked initially, the closer it is, the more natural the transition will be. So, depending on what your date has said, select a follow-up in the moment and tie it to anything she said in her answer.

Standard Question: Where did you come from?

Suggestions for Further Research:

  • Was it a pleasant area to grow up as a kid? Did you ever wish you lived someplace else as a kid?
  • Is there any location that seems like “home” to you besides that town/city?
  • What would you suggest seeing or doing if I came to visit your hometown?

Standard Question: Do you have any siblings? 

Suggestions for Further Research:

  • What was your family’s “identity”? Some kids are the overachiever, the goody-two-shoes, the wild one, or the peacemaker, to name a few. What was your strategy?
  • Are you or have you ever been closest to one sister in particular?
  • What makes you stand apart from your siblings?

Standard Question: How did you end up in this city?

Suggestions for Further Research: 

  • What has shown to be the most different from your pre-move conceptions/expectations of this location – what you anticipated it would be like before you arrived?
  • What do you like most about living here?
  • What is one aspect of this city that you first disliked but have come to appreciate?
  • What is one disadvantage of living here that you do not believe you will ever get accustomed to?

Standard Question: What school did you attend?

Suggestions for Further Research: 

  • Did college live up to your childhood notions of what college will be like?
  • What is one thing you wish you knew before starting college? Do you have any regrets regarding your college experience?
  • What do you yearn for the most from your college years?
  • When did you decide what you wanted to study?
  • Is your current job in any way linked to your major?
  • Have you kept in contact with buddies from high school or college?
  • What was the first time you met your best friend?
  • What about how you’ve changed since high school/college would most surprise your high school/college friends?
  • What do you believe the most difficult aspect of growing up has been?

Question: What do you do for a living? Is it to your liking?

Suggestions for Further Research:

  • What are the aspects of your work that prevent it from becoming a dream job?
  • What are your working hours and schedule? Do you like that routine, or are you a natural morning person or night owl?
  • What component of your morning ritual enables you to have a productive day?
  • When you arrive home, how do you prefer to unwind? 

Is there anything on television that you really enjoy?

 Suggestions for Further Research: 


  • What’s a program that you believe was canceled too soon?
  • When you’re at a loss for what to watch, what program do you turn to?
  • Is there anything that you could watch again and again?

Typical Question: What kind of music do you enjoy?

Suggestions for Further Research:

  • What was the most memorable concert you’ve ever seen? Worst?
  • What was the most humiliating concert you’ve ever seen (for example, One Direction in 10th grade)?
  • What is one record that you never grow tired of listening to?
  • Is there a genre of music that you used to like but now can’t stand?
  • What songs do you have on your exercise playlist?

Question: Have you read any excellent novels recently?

Suggestions for Further Research:

  • What was your favorite book in high school that you had to read?
  • Are there any novels you’ve read twice (or more) because you adore them?
  • Is there a book that, although not necessarily your favorite, keeps jumping into your mind the most?

Is there anything you like doing in your spare time? What are your favorite weekend activities?

Suggestions for Further Research:

  • What’s a passion you’d want to pursue if money and time weren’t an issue?
  • What was the fastest pastime you picked up and dropped?

Is it common for you to like traveling? Have you been on any recent vacations? 

Suggestions for Further Research:

  • Is there a specific site or destination you prefer to visit on a frequent basis/return to?
  • Is there somewhere you’ve been that hasn’t lived up to your expectations?
  • Is there somewhere you’ve been that has surpassed your expectations?
  • Which attraction should you go to first while visiting a new city?
  • Which would you pick if you had to live full-time in an RV or on a sailboat?
  • Would you rather spend your holiday in the mountains or by the sea? Did you know that those who favor the mountains are more introverted, while those who love the seaside are more outgoing, according to research? Do you think of yourself as more introverted or outgoing?

What’s anything you’re looking forward to in the near future, just as a general question?

Follow the standard-question-interesting-follow-up pattern outlined above, and your first-date talks will flow easily, you’ll cover a lot of territory, and you’ll never run out of topics to discuss!



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The “fun questions to ask on a date” is a list of questions that can be asked during a first date. These questions will help you get to know the person better and have fun conversations that are not awkward.

Frequently Asked Questions

What is 21 questions to ask a guy?

A: A good question to ask a guy is whats your favorite color. Some other questions are, What was the first album you ever purchased? or If you could take anything from this room with you where would it be?

What are fun dating questions?

A: What are fun questions to ask someone?

What should we talk on first date?

A: Try to open an easy topic of conversation like sports or video games and see how the other person responds. If they are too shy, try asking them about their work/school.

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