6 First Date Questions That Won't Bore Him (Or Scare Him Away)

This is how to ace your first date!

Get To Know You Questions To Ask On A First Date by Szabo Viktor on Unsplash

Communication is the basis of any relationship, so it should come as no surprise that on a first date, effective communication should be something you're focused on. If you're worried about what questions to ask on a first date, don't sweat it.

Lots of people struggle with figuring out what to talk about on a first date so that they don't feel like they're being too vague or interrogating their date.


RELATED: How To Have A Great First Date (& A Second & Third)

You may have already looked up cute first date ideas or things you can do to impress. You already picked out an outfit, the perfume you'll be wearing, had your facial, got your nails done, and maybe even a new hairstyle — you're confident about your looks.


But you still have no idea what you're going to talk about on your first date! You don’t want to have an awkward silence nor a weird conversation, right?

Your first date is a big deal because it's going to determine if you're going to see him again or not. First dates are all about getting to know someone. Your questions should be light so that your conversation will be organic and flow naturally.

You will probably find two types of questions to ask on your first date (if you have done your research). There's the "basic question," the “What’re your interests and hobbies?”

And then there are "unique questions," like, “If you could spend a day with any fictional character, who would it be?”


Basic questions can be boring, especially when the person you're dating has been to other dates before. On the other hand, unique questions can be overly scripted, and your date has to process the question or do a lot of thinking before he can come up with an answer.

This can make him feel like he's being interviewed for a job.

It's OK if you use these two types of question on your date — in fact, using basic questions will help put your date at ease because he can answer these questions without overthinking them.

To make your conversation more exciting though, you need to ask follow-up questions that are interesting. You'll need to share information about yourself or even your answer to the questions you've asked.


It shouldn’t be one-way communication; it’s a date — not an interrogation. Thus, it should be a conversation or an exchange of ideas between the two of you.

Here are some examples of basic questions with interesting follow-ups:

1. How was your day?

  • Did anything interesting happen today?
  • Did you receive any good news today?
  • What was the best part of your day?

2. Where did you grow up?

  • Was it fun growing up there?
  • What places would you recommend visiting in your hometown?
  • What is the most memorable experience you had growing up?
  • Do you have any nicknames?

3. What do you do for a living?

  • Do you like it?
  • What would your dream job be?
  • Did you think you'd end up doing what you're doing?

RELATED: 3 Questions To Ask Yourself First If You Want To Have More Fulfilling Dating Experiences


4. What kind of music are you into?

  • What album do you never get tired of listening?
  • What's the best concert you've ever been to?
  • Can you play a musical instrument?

5. Do you like to travel?

  • What place did you visit that exceeded your expectations?
  • Are you afraid of going to a different country alone?
  • What is your dream destination?
  • What life lessons did you learn from traveling?

6. What hobbies do you have?

  • What are you really into right now?
  • Why did you start your hobby?
  • What are you most passionate about?
  • Does your hobby influence your choice of friends?

You should also stay away from these topics:

  • Your ex or your date’s ex
  • Politics
  • Religion
  • Marriage
  • Money
  • Anything about sex

Remember to relax and have fun on your first date. Keep your first date light and positive, it’s all about getting to know a person. Set realistic expectations. You don’t need to impress him too much. Stay true to yourself and with what you want. When you and your date are relaxed, you can talk about anything smoothly.

RELATED: What Your Date’s Coffee Order Says About Their Personality


Esther Bilbao helps mentor women to have better relationships, health, and personal development. For more information on how she can help you create a better life for yourself, visit her website for a 30-day all-access pass for lessons from expert instructors.