What Questions Should You Ask on a First Date?

Ahh… the first date is here and now you find yourself wondering what you should say, wear, and how the date is going to go overall. You wonder how you can keep the conversation going in a way that won’t make it seem like a job interview under rapid fire. Relax, you’ve got this!

Have you ever heard the saying, “There’s no such thing as a bad question”? Well, we would agree with that to a certain extent. Read on to learn more about topics to focus on rather than specific questions. This will help you to keep your focus and attention on your online dating match and out of your noggin’.

two singles on a first date smiling and talking

Asking Questions About Work

What a person does for work is usually something they take a lot of pride in. Some people have spent years and years studying topics and mastering skills in order to perform the job that they do day in and day out. Inquire not only what they do for work, but what it took for them to get there, training, schooling, etc.

Ask about what things they enjoy most about their job. Maybe they travel for work and you’ve always wondered what that would be like? Maybe they just got a promotion, ask them what their new role will entail. If they mention some sort of project or anything you are unfamiliar with, tell them you’re not familiar and ask them to explain it to you.

Talking About Education

If education is important in an online dating match to you, then you can inquire about a specific degree someone has, or what college was like for them if they lived on campus. Just remember, not everyone has an expensive piece of paper hanging on their wall at home, some people grew up in the school of hard knocks.

Regardless of their educational background, they have a mind full of knowledge maybe even about issues and topics that you do not know about. Perhaps they are a journalist and they know how the newspapers are printed every morning? Maybe they work in an animal shelter and run the weekly pet adoption event? You never know, unless you ask.

Asking About Family & Friends

This is an area that is near and dear to a person’s heart, family and friends. It is important to get a good grasp of what the quality of their relationships are like with their parents and siblings, as this will give you a good idea of what a relationship with you would be like. Do they have a lot of friends, or only a few? We are always advocating for quality over quantity.

Recreation, Hobbies, and Fun

Lastly, but not least, you want to know what sorts of hobbies they have. Do they have an amazing vinyl collection, love to jet ski, and make a mean vegetable lasagna? Do they enjoy reading to help grow and expand their mind? Maybe they don’t have a lot of time for hobbies, in that case, ask them if they had time to do whatever they wanted what would that look like?

Hobbies change over time, so ask about any hobbies they had when they were a kid. This is always a great way to connect with someone when you help them to recall a fond memory from their past. You never know, maybe you had the same hobby as a child? Can you say Matchbox Cars, oh yeah!

The Bottom Line

There are endless questions you could ask your online date, the good news is that you don’t have to come up with all the questions, they will (and should) meet you halfway and ask about half of the questions. Just remember the acronym F.O.R.E. (family & friends, occupation, recreation, education) and this should help get you through the night if you get too nervous.

Always be like a human sponge and remember that every person you meet has something unique and wonderful about them. Also, if there doesn’t seem to be a romantic connection, you can always see if a potential friendship is possible. And lastly, always remember to take some deep breaths to help keep you relaxed throughout the date. Have fun and be safe out there!

For more tips be sure to check out our guide on meeting an online date for the first time.

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Author: Matt Seymour, MSF

Matthew J. Seymour is a dating industry expert with over a decade of experience coaching singles, reviewing dating apps, and analyzing trends within the industry. Matt is a published author with his most recent work “Get More Dates: How to Master Online Dating Apps” that hit shelves in 2023. With a Masters of Science in Finance (MSF) degree from the University of Florida and extensive knowledge of the innerworkings of the online dating industry, Matt frequently serves in an advisory role to some of the largest dating apps on the market. In Matt’s current role with Healthy Framework, he leads the interview team that regularly interviews key dating industry leaders, and leverages his financial knowledge and dating app experience to review and share what singles need to know to get the most out of dating online.