6 Questions to Help You Actually Get to Know Someone on a First Date


Whether you can’t find the perfect outfit for a date or are looking for the nearest exit when you’re actually on it (guilty!), first dates are an inevitable step in the process of dating someone new. Aside from the fact that you might already know your date’s job description from stalking their LinkedIn or how they celebrated their grandma’s 85th birthday from their Instagram stories, it’s not easy to create meaningful conversation in person when our lives are highlighted online. While you shouldn’t ask all of these questions at once (because this is a date and not an interview), here are six first date questions that will help you get to know your date better and hopefully form a connection (filters and hashtags not necessary).

1. “How would you describe your family and friends?”

Let’s be honest: You are who you surround yourself with. How your date describes those closest to them will give you insight on what they deem important and who they are when they’re not on their best behavior. If their friends are outgoing, they probably are as well, or if they’re close to their sibling, they most likely see family as a top priority. Also, the way your date talks about their loved ones is a great indication of the type of person they’re looking to love in the future. 


2. “What’s your dream vacation?”

While you might base the quality of a trip on the view of the city skyline from your 5-star hotel room (you deserve nothing less, obviously), your date could be living for the crackling of a campfire in the middle of the woods. By identifying your partner’s ultimate adventure, you’ll have a better idea of how open they are to exploring the world and how compatible they are to being a part of yours. Of course, your definitions of “dream vacations” might not (and probably won’t) be the exact same, but their answer will give you some insight into how they enjoy life or prefer to spend their free time.


3. “Do you like your job?”

Not to be confused with the classic “what do you do for work?” question, this approach offers you the chance to learn how your date feels about what they do for 40+ hours per week, not just about what they do. How they feel about it will tell you everything. Do they love their job because they get to help people? Are they focused on a side hustle because they want to be an entrepreneur? Are they passionate about what they do, or are they more passionate about a hobby? With this simple question that calls for a detailed answer, you’ll not only gain knowledge on your date’s drive and passion but also on what their career goals are. 


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4. “What do you like to read?”

No matter how many times your date compliments your dog (because who wouldn’t?) or laughs at your sarcastic jokes (duh, you’re hilarious!), you can’t always be sure what they truly like and don’t like (except that you know they’re a dog person, so they get extra points for that). Asking what they like to read is another way to find out if they’re interesting to you or if the two of you are compatible. Maybe they read every article based on their zodiac sign, or maybe they’re into sci-fi novels. Maybe they prefer non-fiction self-help books or are a huge Harry Potter nerd like you. Through hearing what your date does (or doesn’t) read, you’ll have a greater scope of their interests, hobbies, and values and how they all compare to your own. 


5. “What do you need most out of your relationships?”

So there are those common first date questions like “what happened with your last relationship?” or “what are you looking for in a partner?,” but don’t we all have rehearsed answers to those questions after all this time? Knowing their relationship style and needs is crucial to learning more about your compatibility together, so tapping into what relationships are like for them will give you more than the rehearsed past-breakup story or the “someone who is funny, nice, smart” answer we typically get when asking what others are looking for. 

As we’ve learned from the love languages, awareness of how your partner wants to be loved is just as crucial as knowing how you want to be loved. While you might feel loved through physical touch, your date may feel most secure with a lot of quality time. Many couples have different love languages, but if your date isn’t interested in PDA (even not in public) and you travel or are busy with work and friends for most of your time, you might be able to predict what some issues would be if you were in a relationship. 


6. “What makes you happy?”

Insider tip: The responses to these questions are obviously crucial, but their reaction and enthusiasm while discussing their relationships, interests, and life are also key. You can and probably will be different from every relationship you enter. You’ll probably have different interests, like different kinds of music, or argue over which type of food to order for Friday night takeout. The one similarity that is most important though? Outlook on life.

If you’re passionate about your job or feel your happiest around your family and they light up when talking about their parents or are excited to tell you about a side hustle they’re starting, you’re probably similar in some of the ways that matter. Asking them what makes them happy might feel like a loaded question, but their answer will tell you a lot about what your relationship might be like, whether their idea of happiness is hanging out at home with their family, having the freedom to sleep in, or tuning into their adventurous side and trying new things.


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