10 unexpectedly fun questions to ask on a first date, according to a relationship expert

It’s a common modern dating conundrum—you matched on Hinge a week ago, and while on the app, the conversation was flowing. Now you’re face-t0-face getting a cocktail at a swanky neighborhood bar, and all you can think to talk about is tax season. Or the election. Or the bomb guacamole you had with your lunch. While guacamole isn’t the worst topic you can discuss on a first date (it’s important to know if someone is an avo fan of the bat, anyway), there is something to be said for having first date questions in your back pocket that you know will lead to interesting conversation. According to Dr. Carla Marie Manly, clinical psychologist and author of Joy from Fear, preparation has a way of calming nerves.

“Feeling prepared for anything, whether a job interview or a first date, can be very calming and stress-relieving.  Many people find that having a few questions in mind for a first date can reduce fear and nervous energy,” Dr. Manly tells HelloGiggles. “Sometimes a first date will flow easily and the prepared questions won’t be necessary to spark dialog, but in other cases it can be very helpful to have questions to promote causal conversation.”

So why not open the floodgates with some compelling questions? Forget the standard, “So, what do you do?” and spark some in-depth discussions that get a little personal in all the right ways. Consider popping a few of these questions on your next first date and see where they lead the conversation. If nothing else, you’re bound to get some interesting answers.

What’s your most vivid childhood memory?

Maybe their favorite childhood memory is about being with their pet dog in the backyard or the smell of their grandmother’s house. Childhood memories are funny things: They reveal a lot about the way someone thinks about the world, and the way they looked at it from a young age. It’s a great way to learn a little bit more about their background and spark a discussion about the way you both grew up.

Tell me about your family

You want to know where someone came from, but it can be a delicate subject. (Maybe their relationship with one of their parents or siblings isn’t great.) This is a nice way to leave it open-ended, and let your date chat about their family in terms that are as specific or as general as they want. It shows interest without being intrusive.

What’s the worst advice you have ever given to someone?

This a thought-provoking question that you can dive into somewhere in the middle of the date, when things are starting to feel more comfortable. It can provide you with some insight into how your date has learned from past experiences, and also potentially lead to a funny anecdote they hadn’t originally planned on sharing.

“Open-ended questions […] build connection by inviting deeper dialogue rather than a simple ‘yes’ or ‘no’ response,” Dr. Manly says.  “Questions of this nature also provide insight on the person’s background and interests without being too invasive. The responses to these seemingly basic questions can give wonderful clues to your overall level of compatibility.” And that’s something you definitely want to figure out on a first date.

What’s the worst (or most embarrassing) situation you’ve ever found yourself in?

This definitely isn’t something you should lead with, but it is a fun one to pull out if there’s a lull in conversation. “Questions of this nature can be great fun because they invite either whimsical reminiscing about the past or wonderful imaginings about possibilities,” Dr. Manly says. “The responder can feel free to dive into the responses or take them at a light and superficial level. This takes the pressure off to reveal too much, but it also provides the opportunity to reflect and share a great deal.”

What’s something you’ve been really proud of lately?

Maybe for your date, something they’re currently proud of is hitting a time goal on a run, or learning how to make pesto, or finally getting the hang of something at work. It opens up room to hear about what they value without making your date feel like they’re bragging. And you can share, too!

What’s the last book you read?

If reading is something you’re into, this is a good way of seeing what tastes you share and what interests your date has. And even if books aren’t your thing, Dr. Manly suggests asking about the latest series on Netflix they watched in one day, or their all-time favorite movie that they never get sick of. You’re sure to find a common ground somewhere in this discussion.

What’s something you’ve always wanted to try?

Bungee jumping? Kayaking down the Amazon? Eating that super-hot chili on the “Dare You” menu at the local diner? It’s a good way to take a peek into their ambitions and dreams, while sharing some of your aspirations as well. Nothing is too big or small for this conversation.

What are you looking for?

If you’re going out together, it’s fair to assume that you and your date are both in the dating game, but other than that, you can’t really assume anything else. “We often fear asking the ‘What are you looking for question,’ but I believe it’s as essential and basic as knowing what type of job you want before putting in resumes,” Dr. Manly says. “Dating takes a great deal of time and effort, so it’s important to know as early on as possible if you’re on the same page as to what you’re both looking for in a relationship.” Don’t be afraid that the question is demanding any sort of commitment from the jump Dr. Manly says, but instead “see this question as a pragmatic, intelligent, and necessary part of dialogue that helps both people known if their goals are aligned.” The more direct you are, the more time you’ll save in the long run.

What’s the most amazing travel adventure you’ve been on?

Is your new date a big traveler? Are they keen to explore their city, and find some of the most unique restaurants or parks in the area? Whatever the case may be, this is sure to lead to a fun chat where you may be able to learn what you want to put next on your to-do list.

What things would you save if your apartment were on fire?

For me, it would be my photo albums and my childhood stuffed animal, but their question will tell you what they could not bear to lose. And what the select might surprise you. The goal of dates is to have a good time and figure out if you want to see more of this person. Hopefully some of these questions will help you on your way.

First dates will always be nerve wracking, no matter how prepared you are, but coming to the table with some questions can ensure that that tension melts away relatively quickly. And who knows, it could lead to a second date.

Additional reporting done by Kristin Magaldi.

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