The Best Questions to Ask on a First Date

Conversation starters

Like the title suggests, these questions are the best option to start a conversation on a topic. The idea is to start with an easy question that will lead to a more in-depth conversation about anything you like: music, cinema, video games, etc. Some of the best ones you can use are:

What do you like to do in your free time?

If you still haven’t discussed your hobbies through DMs, then this is the best time to ask about them. If you end up having a common interest, you can discuss it more. For example, let’s say you both go to the gym and like to live a healthy lifestyle – you can then share tips and tricks to make workouts more effective or how to train muscles that are difficult to tone.

What tv show or movie do you like to rewatch?

Everyone has at least one TV show (or movie) they love and have watched more times than they want to admit. This question is an excellent conversation starter, as it always leads to a win-win situation. If you both love the show, you can spend quite a while sharing your favorite scenes. If not, then you’ll discover a new TV show to binge-watch. You can even tell your date that you’ll watch it and come back to them with your review.

More than anything, the main goal of a first encounter is to get to know your date. However, it might be a little awkward if you start a full-blown interrogation. Instead, use these more subtle questions that will allow you to understand what kind of person your date is.

What’s your favorite thing to do outdoors? How about indoors?

Basically, you want to find out what activities your date enjoys. Not only is this perfect for finding out if you share common interests, but it’s also an excellent way to get ideas for a second date.

If money wasn’t important, what would be your dream job?

This is an ideal method to find out about your date’s current job, their career goals, and their dream job. This is also a good way to understand if they have decided to put their career dreams on hold for financial stability.

What are people often surprised to learn about you?

This question can lead to a variety of things: an interesting personality trait, a guilty pleasure, an unexpected hobby, etc.

Deep questions

Depending on how the date’s going and how comfortable you feel with this person, you may want to cut to the chase and go for some deeper questions. This is how you learn more about your date’s childhood, family, philosophies, biggest regrets, and more.

If you could give everyone one piece of advice, what would it be?

Usually the answer to this question is strongly attached to something difficult that the other person has been through. You can ask them to elaborate a little more on the reasons behind their choice and share your own experiences.

If you knew you were going to die in a year, what would you change about how you live?

This is a great way to start a serious conversation about what you and your date have been postponing. Sometimes we feel that life lasts forever, so such exercises are great to know someone on a deeper level.

There are many other questions you can ask. And regardless of whether you choose to have a light first date or a more serious one, always remember that the most important thing is for you to be yourself and have fun. The date may not go anywhere, but since you went through the trouble of dressing up, you might as well make the most out of the time you’re spending with this person. Who knows, even if they aren’t the one, you may end up with a friend for life.