10 Most Important Questions to Ask on a First Date

Few people are entirely comfortable when talking to a person they’ve just met. It’s why first dates can be anxiety-producing situations. You don’t ...
first date

Few people are entirely comfortable when talking to a person they’ve just met. It’s why first dates can be anxiety-producing situations. You don’t know what to expect until you get to know the person better and sometimes it can be challenging to come up with questions that are helping you and your date to relax and go beyond “what’s your favorite color”- type of questions.

We compiled a list of 10 most important questions you should ask your date if you can’t decide what to ask your potential partner. In addition to your must-have items on a first date, make sure to bring these new questions as well.

1. What is the most important thing in your life?

First off, usual conversation starters such as questions about your date’s private life are a little too private for a first date. It’s why you should go with neutral questions first. By asking what the most important thing in his or her life is, your potential partner will uncover what they cherish the most.

2. What do you like to do outside of work?

Work-related questions are often boring to the person you’re talking to, so try to steer clear of them. Instead, asking what a person does outside of work will give you a glimpse of what their hobbies are and how they spend their free time. Maybe you two have something in common, so this is the perfect question to find out.

3. Where do you see yourself in 10 years?

People who live for today are real free spirits. Nevertheless, thinking about the near future is essential, especially if that future consists of a specific lifestyle. You might discover that your date wants the same future as you do. Or, on the other hand, they might say the opposite of what you had in mind.

4. Do you have a bucket list? If yes, what’s on it?

A bucket list can tell you many things about a person. For example, you’ll find out if they are adventurous, or more of a stay-at-home person. Moreover, a bucket list question leads to additional questions, such as “Why would you go ziplining? Do you enjoy nature?” etc.

5. What is the most crucial trait you value in your friends?

When you’re going into a relationship with your dates, you will inevitably become friends with their friends. However, it’s helpful to know what your potential partner appreciates in his or her friends. If you have the same trait, you have more chances of going on a second date.

6. If you could, what would you advise your 10-year-old self?

This question serves as a disguised “Do you have any regrets?” question. Your date will uncover what kind of person would he or she like to be and which decisions would they change had they had thought differently in the past. You can find out about the tough situations in their life, as well as how they would handle those kinds of situations now.

7. What’s the worst date you ever experienced?

This question helps you to know what kind of dates your date doesn’t like. It can also be a learning curve for you, giving you an insight into what you should avoid doing. If a girl tells you how one time her date didn’t bring condoms on a date, and it was irresponsible of him, make sure to bring them next time.

8. Do you like your job?

We said that job-related questions are annoying. But not if you ask about the feelings a person has towards his or her job. If they hate their job but are still working there, do they really hate it that much? Also, are they afraid of telling their boss of what bothers them and would rather stay quiet about it? This question can uncover more traits about the person; whether they’re shy and quiet or decisive and always telling if there’s a problem.

9. Do you know any good books?

Behold all of you bookworms out there. Some people don’t read very much, so instead of asking “Do you like to read?” on which you can get a “yes” or “no” answer, ask him or her if they know any good books. You might get an excellent recommendation. 

10. What would you do if you won the lottery?

The last question reveals if the person’s greedy and likes to spend money on silly things or if they’re careful with their funds and prefer to invest. The answer can tell you more about how a person deals with their finances and what kind of future they would like to make for themselves.

What Is Your Favorite Question to Ask on a First Date?

Do you like our list? We’re aware that you probably won’t remember half of these questions on a first date, but the crucial thing is to be sincere and genuine while talking to your date. That way you’ll be able to relax more and to have fun with the person you just met.


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