Questions To Ask (And Not To Ask) On A First Date

By Jessica Huhn for DateAha!

So, you’ve taken the next step. You’ve met someone who seems like a good fit online, and the two of you are ready to meet in-person for the first time.

The first in-person date is a crucial time to learn who your match truly is as a person. But, it can also bring the nerves. What are the best ways to get to know your date more deeply, and see if you want to have more dates with them in the future? Asking lighthearted questions is the perfect way to get to know your date better, while making sure your date doesn’t get too serious or uncomfortable.

Here at DateAha!, we’ve compiled a list of great questions to ask on a first date (plus some questions to avoid until you’ve entered a longer-term relationship…and some to always avoid.)

Photo by Huy Phan on Unsplash

The Yes List

Many of these great first date questions will work well for online conversations, too! One word of caution, though: Don’t bring a scripted list of questions to your date, or make the questions you ask sound preplanned. Instead, just let the conversation flow, and have these questions in mind in case you need fuel for your conversation — goodbye, moments of dead silence! We’ve organized these questions into 5 categories.

1. Anything-But-Basic Twists on Basic Questions

• What makes the perfect day for you?
• What were you like as a kid?
• What was the most interesting thing you’ve done in the past year?
• What’s your typical day like?
• How would your friends describe you to me if you weren’t in the room?
• What are your favorite memories?
• What is your earliest memory?
• When you were a kid, what did you think your adulthood would look like?
• What’s the most spontaneous thing you’ve ever done?
• Other than your parents, who has taught you the most about life?
• What’s the #1 thing you think I should know about you?

2. Passions

• What are you most passionate about?
• What are your favorite hobbies?
• Are you working on any passion projects?
• Where is the most interesting place you’ve ever visited?
• What’s the #1 item on your bucket list?
• What’s one thing you’re hoping to do within the next year?
• What’s your dream job?
• If time and money didn’t matter, and you could try out any new hobby, what would you choose?

3. Media Interests

• What is your favorite book?
• What is the last book you read?
• What’s your favorite TV show?
• What good movies/TV shows have you watched lately?
• Are there any new movies you really want to see?
• Have you listened to any good songs lately?
• What’s your favorite (musical) artist or band?
• Who would you cast as you in a movie about your life?
• What 3 fictional characters best describe your personality?

4. Dislikes

• Do you have any pet peeves?
• Is there anything you don’t eat?

5. Questions That Give Insights Into Your Date’s Personality

• What’s the best piece of advice you’ve ever received?

This will subtly help you find out areas of struggle for your date, without being upfront about it.

• Would you rather eat bugs or swim with sharks? Would you rather be rich but not famous or famous but not rich? (Or any “would you rather” question)

Besides being a fun icebreaker, “would you rather” questions can be an easy springboard into deeper conversation. Why would they choose swimming with the sharks over eating bugs, for example? Any question could be followed up with a “why,” but “would you rather” questions make this easier than most.

• If you won the big lottery jackpot, what would you do with the money?

Based on their answer, you’ll know if they would be selfish, compassionate, or a bit of both.

• If you could switch bodies with anyone for 24 hours, who would you switch with and why?

Whose shoes would they want to walk in? Or, who would they want to control (possibly to make meaningful change)?

• If you could have any superpower, what power would you choose?

The power gives insight to their personality…and did they think about their answer?

• If you had to be an animal for a day, which animal would you be?

Animal traits can be huge windows into your date’s personality. For example, do they pick a bold lion? A free-flying bird? A small animal who can observe people almost unseen?

• If you could learn any skill overnight, what skill would you choose?
• If someone gave you a plane ticket to anywhere in the world, but you had to use it tomorrow, where would you go?
• If you could witness any event in history, what event would you choose?
• If you could talk to anyone, living or dead, who would you choose and why?
• If you had the option to see part of your future, would you look ahead or refuse?
• What’s the best gift you’ve ever given? Ever received?

Photo by Marvin Esteve on Unsplash

The Caution List

Some heavier topics are ok for on the first date, but these questions might be best left for the second or third date, so you don’t leave behind the lighter feel that a first date should ideally have. Remember: you should ask these questions eventually — just not right away.

• What are you looking for in a relationship?
• Do you have kids?
• Any political question.
• Religious questions. (It’s perfectly ok for you to casually and briefly mention your religion on the first date. Just don’t throw your match under the bus and ask them a direct religious question).
• Questions about long-term plans for the future. (It’s ok for you to briefly talk about your own long-term plans and see if they volunteer. Again, though, don’t throw them under the bus.)

Photo by Sweet Ice Cream Photography on Unsplash

The No List

These questions are too personal and heavy for the first date. Save these for much later dates.

• Do you have any debt?
• How much money do you make?
• Are you stable or struggling financially?
• Any money question. (Basically all money matters are off-limits on the first date.)
• Could you tell me about your last serious relationship? Why did it end?
• Were you in other relationships before? What were they like?
• Are you currently seeing anyone else?
• Where do you see this relationship going? (Seriously, you just met in person for the first time. This question is way too much pressure, way too soon!)
• What is your most embarrassing moment? (This puts your date in a way too vulnerable and uncomfortable position.)
• What’s your biggest fear? (Another uncomfortable one best saved for later.)
• Do you have any health issues?
• What are your deal breakers?
• Are you interested in having children?

Photo by Mark Riechers on Unsplash

The Absolutely Not List

These questions are never appropriate for any date!

• How many people have you slept with?
• Where are you really from? (This is totally racist.)
• What are you? (Even more racist than the last question.)
• You’re so attractive, so why are you single?
• Any question about their appearance. (That will make them feel insecure.)
• Any question about your appearance. (This will make your date think you’re insecure.)
• Are you going to eat all of that? (This shames your date for their choices, and indirectly, for their appearance.)
• Could you pay for this? (The person who initiates the date pays…unless you agree beforehand to split the cost. But never ask your date to pay!)
• Any sexual question that could make your date uncomfortable.

One More Key Question to Make Sure You Ask

• Am I what you expected, based on my profile?

This is key to ask because you want to clear up any misconceptions and come across as honest as possible. This may also lead your date to ask the same question back, enabling you to be upfront if something didn’t seem right about their own profile.

But what if something seems off about your date, and they won’t admit it? Like, what if they’re clearly not who they say they are in their profile — much older, shorter, a different weight…or not even the same person? Or what if they mention something that is totally inconsistent with their profile story?

Even worse, what if they behave in a sexually inappropriate — or even abusive — way?

Could this situation have been avoided? And is there any way to warn other daters about this person? After all, the dating sites don’t do anything to hold bad actors accountable.

Turn to DateAha!, a browser extension that lets you leave comments on dating profiles. Now, if you find out someone lied to you online when you meet in person, or experience toxic behavior at your date’s hands, you can leave feedback on their profile and hold them accountable for their actions. Fear of negative feedback will drive bad actors off dating sites and make the online dating climate (including the in-person dates that follow) safer, saner, and much more honest.

Use DateAha! for free comments and messaging on any online dating profile.