60 Questions to Ask on a First Date You Can Count for a Successful First Date

60 Questions to Ask on a First Date You Can Count for a Successful First Date
Questions to Ask on a First Date - Photo by Andrea Piacquadio from Pexels

Tripboba.com - When you’re on your first date, you don’t want things to go wrong, everything has to be perfect – but of course, you want to do it casually without bragging and thinking about messing it up.

One of the most important things to look for during your first date has to be the kind of questions you’re going to ask. Questions to ask on a first date can be difficult to know, having the fact that this is your first date.

However, you don’t have to worry, as Tripboba has got you covered with some of the most on-point questions to ask on a first date.

Let’s find out what we have for you!

Questions to Ask on a First Date

Questions to Ask on a First Date - Photo by vjapratama from Pexels

Our first list of questions to ask on a first date shows through the following list. You can see how each question can get your conversation going.

  • "What do you like to do in your free time?"
  • "Are you more of an indoors or outdoors person?"
  • "Who is the most fascinating person you’ve met?"
  • "What was the last book you really got into?"
  • "What are some movies you really enjoyed?"
  • "What amazing adventures have you been on?"
  • "What pets have you had?"
  • "What’s your favorite alcoholic or non-alcoholic drink?"
  • "What are you kind of obsessed with these days?"
  • "Where have you traveled?"
  • "What’s your favorite international food?"
  • "Are you a morning person or a night owl?"
  • "What’s your favorite restaurant?"
  • "How many siblings do you have?"
  • "What would be your dream job?"

Questions to Ask on a Date

Questions to Ask on a First Date - Photo by Josh Willink from Pexels

After probably going through red flags in the past, it’s your time to shine, not that you weren’t shining before. But today is the day you’ve been waiting for to start over, where you’re going to be out and about with your crush, and potentially will become your boyfriend/girlfriend.

So, here are questions to ask on a first date you can take inspirations from:

  • "What would you do if had enough money to not need a job?"
  • "Who is your favorite author?"
  • "What was the last show you binge-watched?"
  • "What TV show do you keep coming back to and re-watching?"
  • "What hobbies would you like to get into if you had the time and money?"
  • "If there was an Olympics for everyday activities, what activity would you have a good chance at winning a medal in?"
  • "What would your perfect vacation look like?"
  • "Among your friends, what are you best known for?"
  • "What music artist do you never get tired of?"
  • "What are some accomplishments that you are really proud of?"
  • "What are some obscure things that you are or were really into?"
  • "What are some things everyone should try at least once?"
  • "What fad did you never really understand?"
  • "What’s the best thing that has happened to you this month?"
  • "What would your perfect morning be like?"

Fun Questions to Ask on a Date

Questions to Ask on a First Date - Photo by Josh Willink from Pexels

Now, you must include that fun vibe through your first date, so that both of you will feel comfortable with each other, and also that boredom won’t be in the way! This is definitely an important thing to do in your first date, as you may find out that both of you share the same sense of humor or the same hobbies.

You can create fun vibe through fun conversation. And To help you, Tripboba has gathered these fun and unique questions to ask on a first date – and mind you, they can be conversation starters:

  • "Have you ever changed your mind about something you were once sure about?"
  • "If you could invite any three people from history over for dinner, who would you choose?"
  • "What would your perfect day look like?"
  • "If you had to live in an ancient civilization, which one would you choose?"
  • "If you could invent a new ice cream flavor, what would it be?"
  • "What is the most meaningful thing someone ever said to you?"
  • "If you could spend a day with any fictional character, who would it be?"
  • "Cats, dogs, other — or no pets?"
  • "Do you have a signature dish you can cook?"
  • "What personality tests have you taken and do you agree with the results?"
  • "If you could go back in time and do something differently, what would you change?"
  • "Would you rather live a month in squalor with your best friend or a year in luxury with someone you can’t stand?"
  • "If you could solve one world issue, what would it be?"
  • "What is something you wish more people knew about you or don’t know that you’re good at?"
  • "What is something you’ve done in the last year that’s pushed you out of your comfort zone?"

Good Questions to Ask on a First Date

Questions to Ask on a First Date - Photo by Josh Willink from Pexels

To keep the conversation going, you have to be able to carry it into a good mood, and that can be done by asking some quality and good first date questions.

After doing research, here is what Tripboba has found on good questions to ask on a first date:

  • "What do you do to unwind?"
  • "Who is the kindest person you know?"
  • "What’s your favorite piece of furniture you’ve ever owned?"
  • "Where’s the strangest place you’ve ever been?"
  • "What's on your bucket list?"
  • "If you could give yourself a nickname, what nickname would you want people to call you?"
  • "What would you like to know more about, but haven’t had the time to look into it?"
  • "What wrong assumptions do people make about you?"
  • "What is the most beautiful view you’ve seen?"
  • "What’s the most recent thing you’ve done for the first time?"
  • "What small seemingly insignificant decision had a massive impact on your life?"
  • "Where would you move if you could move anywhere in the world and still find a job and maintain a reasonable standard of living?"
  • "What are you most grateful for?"
  • "What did you do last summer?"
  • "What are your pet peeves?"

That was all about questions to ask on a first date from us. We hope that you found what you were looking for!


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