14 Insightful Questions You Need To Ask On A First Date

First dates are a wild mix of excitement, nerves, and anticipation. First impressions matter, and you want to get them right! But if you are feeling a little jittery about your first date, we have a few ways to turn those nerves into confidence. All you need to do is have these fun and revealing questions ready to go! Inspired by therapist Jeff Guenther, these questions will not only break the ice but also help you get a real glimpse into who your date really is. The right questions can spark deeper conversations, help you connect, and make your first date stand out.
Note: The content of this article is for informational purposes only and is not a substitute for professional advice. Always consult with a qualified professional for advice tailored to your individual circumstances.
If A Portal Suddenly Opens Up In Front Of You, Would You Step Through It?

This question might seem a little out there, but Jeff has a point here. It’s a fun way to see how adventurous your date is. It taps into their curiosity and sense of spontaneity. Would they dive headfirst into the unknown, or would they hesitate? Their answer can tell you a lot about their approach to life. If they’re excited about the idea of stepping into a portal, it shows that they’re open to new experiences and willing to take risks. On the other hand, if they’re more cautious, it could indicate they like to play it safe.
What Celebrity Or Public Figure Do You Want To Hook-Up With But Would Never Tell Anyone If It Happened?

This is a cheeky and flirty question from Jeff, giving you both a chance to share a guilty pleasure or secret crush without getting too serious. It lightens the mood and offers a peek into their taste in people, whether they’re into quirky comedians or Hollywood heartthrobs. The playful nature of this question allows you to gauge how comfortable they are with humor and whether they can laugh at themselves and not take things so seriously.
How Long Is Too Long To Wait In Line For Brunch?

This one might seem pretty casual, but it can tell you a lot about someone’s patience and priorities. “How long is too long to wait in line for brunch?” can start a conversation about what they’re willing to put up with for good food and an experience (or if they know it’s your favorite spot, how far are they willing to go for you?) Some people will say they can’t imagine standing in line for more than 15 minutes, while others might say an hour isn’t too bad if the place is hyped enough. This little question can reveal a lot.
What’s Your Favorite Way To Spend A Weekend

This question shows how they like to spend their free time and whether their lifestyles align. Do they prefer quiet weekends at home, or are they always on the go, seeking new adventures? It also opens up the conversation for you to share your weekend routine, helping you see if there’s common ground. Plus, it’s a low-pressure question that can lead to lighthearted stories about their hobbies or favorite pastimes.
What’s One Thing You’re Passionate About?

Asking about their passions taps into what truly excites them, whether it’s their career, a hobby, or a cause they care deeply about. It’s a great way to see if they light up when talking about something meaningful to them. This question can also help you gauge their level of commitment and drive in different areas of their life. Are they passionate about learning new skills, traveling, or making a difference in their community? Passion can translate to motivation and ambition, qualities that might be important to you.
What’s Your Idea Of A Perfect Vacation?

Everyone has a different idea of what makes a vacation perfect, and this question can give you a peek into their travel style and preferences. Some people love adventure and exploring new cultures, while others prefer lounging on a beach with a good book. If they’re the type to plan every detail or fly by the seat of their pants, it can say a lot about their personality. This question also opens up fun possibilities to share your own travel stories and dream destinations.
What’s Your Favorite Book, Movie, Or TV Show?

Asking about someone’s favorite form of entertainment reveals their tastes and what kind of stories or ideas captivate them. Whether they’re into true crime documentaries, classic literature, or reality TV, it gives you insight into their personality. It’s also an easy conversation starter. If you share similar interests, you can bond over them, and if not, you get to learn something new. Plus, it might give you a new recommendation to check out later!
What’s One Thing You’re Grateful For Right Now?

This question goes a little deeper without being too heavy, helping you understand what matters most to them at this point in their life. Gratitude is a great way to see how someone views the world and whether they focus on the positive aspects of their life. Whether they mention family, a recent experience, or a personal accomplishment, it gives you insight into what they value. People who practice gratitude tend to be more mindful and emotionally aware, which can be a huge plus for a potential partner.
How Do You Handle Stress?

Everyone deals with stress differently, and learning how your date handles pressure can reveal a lot about their emotional intelligence and coping mechanisms. Some people blow off steam with exercise or creative outlets, while others may need a quiet night in or a conversation with a friend. This question is a great way to gauge their emotional maturity and how they handle tough situations.
What’s Your Relationship Like With Your Family?

Family is often a key part of someone’s background and how they approach relationships, so learning about it early on can give you a clearer picture of who they are. Whether they’re super close with their siblings or have a complicated relationship with their parents, this question allows you to see how much family influences their life. It can also hint at their values and priorities. Do they spend holidays together, or do they keep more distance?
What’s Something You’ve Always Wanted To Try But Haven’t Yet?

This question taps into their sense of adventure and curiosity, revealing what kinds of experiences they’re excited about but haven’t yet pursued. It could be anything from learning a new language to skydiving, and their answer can help you see if they’re open to trying new things. It’s also a great way to find out if they’re spontaneous or more of a planner when it comes to new experiences. Asking this question could even spark ideas for future adventures together.
Where Do You See Yourself In Five Years?

It might feel like a cliché question, but knowing if your long-term goals align is important. Asking about their future plans gives you a sense of their ambition, priorities, and where they see themselves going in life. Are they focused on building a career, starting a family, or traveling the world? Their answer can help you see if your paths might cross or if you’re heading in different directions. It’s not about locking down specifics but understanding what’s important to them and whether they have a clear future vision.
If You Could Move Anywhere in The World, Where Would You Go?

Does your date have an instant place in mind? Are they a beach person or more of a mountain man? The place they choose can say a lot about their personality. If they choose a big city, they may be more of a partier, but if they choose a secluded island, they enjoy the peace and quiet. See if their destination aligns with yours, and you may instantly see if the two of you are meant to be!
What is the Most Spontaneous Thing You Have Ever Done?

Is your date wild, or are they fairly level-headed? This question will help you get to the bottom of that! Asking your first date about the most spontaneous thing they’ve ever done gives you a glimpse into their adventurous side and how open they are to new experiences. Their answer can reveal a lot about their personality and their sense of fun. It also shows if they are willing to take risks. It is also a lighthearted question that can lead to funny stories and help break the ice!
This article was inspired by the Instagram account of therapist Jeff Guenther.