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10 Questions You Should Be Asking on the First Date

Breaking the ice on a first date can be awkward. When getting to know someone new, it’s important to ask the right questions, but don’t lay it on too thick making the experience feel less friendly and more like an interrogation. Some people date for fun while others date with an end-goal in mind. Regardless of if you’re looking to settle down or simply meet cool people, enjoy the date and take notes at the same time. Here are 10 questions you should be asking on a first date.


How do you spend your free time?

While this seems like a generic question, their response will yield great insight. Get a sense of how they spend their non-office hours. This question alone will also tell you about their hobbies, unique interests, self-care routine, and how they make time for people in their life.  A well-rounded individual usually makes the most of their free time by spending it in an intentional manner. Are they constantly working on a business plan or spending their weekends playing 2K? How busy they are off the clock can usually indicate if they have space for someone new.


Tell me about your most embarrassing moment.

This is a fun ice breaker question that will lighten the mood giving you a good idea of the other person’s sense of humor. How they recovered from the embarrassing moment will show their ability to bounce back and can bring to the surface any pessimistic traits exhibited when caught off guard.


Where did you grow up and how would you describe your childhood?

Here’s a two-part question that can reveal family history and values. Did their parents split at an early age? Are they still navigating traumatic experiences? Do they visit home often? You’ll get to the core without having to do much digging. This question can also bring on nostalgic emotions that can open the door for you to reminisce on moments from “back in the day.” Even if you grew up in different parts of the country, there’s a chance that you two will find unifying experiences from childhood.


How did your last relationship end?

It’s time for some truth-telling. You’ll immediately find out if he or she takes responsibility for their actions. Are they a self-proclaimed victim or mature enough to accept their part in their past relationships. If they blame their ex for the breakup (even though it very well might have been the other person’s fault), you’ll know whether they are still harboring ill feelings and if they’re open to starting something new.


What are your thoughts on *insert current event*?

A first date is a great time to learn where a person stands on today’s social climate.  You can casually slide this into conversation by saying, “This came across my feed today” or “Did you see this on Twitter?” You’ll learn a great deal about their personal views. Be open-minded. It never hurts to consider a fresh perspective. Tread lightly with this question because things could go left rather quickly. And watch out for debates! Seriously, getting worked up or forcing your opinion on someone you’re not even sure that you want to spend extended periods of time with ain’t worth it, sis.


What qualities do you look for in an ideal partner?

This question cuts straight to the chase and will let you know exactly what they’re looking for in their next relationship. Do you meet their expectations? Better yet, do they meet yours? Their response will ultimately determine whether or not you’re up to a second date.


Where do you see yourself in the next five years?

This question is super important to ask on a first date. Is this person actually living or merely existing?  A five-year plan will vary from person-to-person but it will reveal their attitudes on the future, if they’re actually working toward building a better life for themselves, and will determine what actionable steps they’re willing to take to reach a goal.  Their response will likely pinpoint whether they’re interested in marriage and children. No one has it all figured out, but it’s nice to know if your plans align.


What’s your love language?

Do they need words of affirmation to feel loved? Are gifts a priority in making a relationship work? Do they require acts of service to be performed by a partner? Are they a stickler for spending quality time with loved ones? Do they require physical touch to maintain a loving bond? If they don’t ask about your love language in response, take this as a hint that they aren’t too interested in getting to know you just yet on a deeper level.


Who are the most important people in your life?

Outside of family values and past romantic partnerships, you’ll find out if the other person knows how to maintain personal relationships. How big are they on communication? Are they a social butterfly or prefer less interactions with humans? Do they nurture their friendships?


What are your thoughts on therapy?

This question will go beyond the surface and could change the tone of the date to a more serious atmosphere. Only ask this if you’re really into the other person. Pressing someone on their mental health can get intrusive, depending on how you swing it. If the other person seems leery or dodges this question, you’ve likely hit a boundary for them. And they’re within their rights not to go deeper with you. A first day won’t necessarily present a person’s mental stability, it can reveal how serious they are about health and wellness.  If they aren’t interested in taking care of their own mind, body, and soul, chances are, they aren’t emotionally available to prioritize your well-being.



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