It is the modern-day Scream saga, painstakingly nerve-racking and quite brutally torturous. Dating comes with a set list of challenges, particularly living during the age of “a better lover a swipe away.” Everything is moving fast, and love has never moved at a more rapid pace. In the rat race to find the person who makes you feel like you have everything you deserve, it is easy to get lost between the fish photos and the generic small talk. If you are a human who is on this journey like me, you have also endured a couple of first dates and you would know that it is sometimes a blood bath of boredom. Through personal experimentation, conversation with fellow daters and extensive googling I have compiled a list of questions that can transform even the most mundane conversation into the best date of your life!
Question 1
Who is the person you love most in this world?
Giving another human the title of “most loved in the world” is a profound gesture. The way your date speaks about this person—their opinions, character, and morals—can reveal a lot about what they value. Pay close attention to how they describe their most cherished connection. Are they focusing on beauty, intelligence, or accomplishments?
You can learn so much about someone through the qualities they admire in those they hold dear. What do they notice about this person? What do they prioritize in a meaningful relationship? Reflect on their perspective and ask yourself: Do they love the same things I cherish about this human experience? Or perhaps they’ve noticed something beautiful that you haven’t yet considered
Question 2
If money weren’t a concern, what would you do?
This question encourages the person to reevaluate how they spend their time, stripping away the constraints of time-consuming capitalism and opening their mind to endless possibilities. Often, their answer will highlight the things they love to do, dream of doing, or wish they could do.
As you listen, reflect on their response: Do we value the same things? Do we enjoy spending our time in a similar fashion? Are we creating corresponding realities?
Question 3
What is your favorite book of all time?
If you’re a human navigating modern society, you know that we’re constantly consuming information—just like you are right now, reading these words. Whether you’re an avid reader or not, reading is a fundamental part of how we engage with the world. The type of content someone chooses to absorb says a lot about how they shape their worldview and perceive others.
If your date isn’t into reading, don’t worry—you can always pivot the question to podcasts, audiobooks, or TED Talks. Pay attention to the finer details of their explanation: Why did this piece resonate with them so deeply? What drew them to it, and what did they take away from the experience?
Question 4
What makes you feel most alive?
Question 5
Tell me something you normally wouldn’t share on a first date.
Without a doubt, this is the ultimate question for sparking meaningful and fun conversations. It often leads to a good laugh, which is perfect for easing the awkwardness that can come with first dates. A lighthearted moment like this can quickly brighten the mood and help both of you feel more comfortable.
Be prepared to answer the question yourself—if it catches your date off guard, sharing your own response first can create a safe and inviting space for them to open up. This approach not only fosters connection but also sets the tone for a more relaxed and enjoyable conversation.
Question 6
What is your definition of happiness?
By asking someone to define happiness, you’re indirectly inviting them to reflect on their own life experiences, societal perceptions of happiness, and their personal views on its importance. This question can offer valuable insight into how your date perceives joy and how it manifests in their reality.
Be open to receiving light or superficial answers—after all, it’s a first date. If things go well, you can revisit this question on a second date for a deeper exploration. Together, you can unpack their response, allowing it to be frivolous, limitless, or even philosophical.
Question 7
Do you believe in marriage, and do you want children?
This might be a controversial choice for a first-date question, but let’s be honest—both of these topics are deal breakers. Why should we always avoid discussing what we truly want just to make others feel comfortable? It’s better to ask the uncomfortable questions upfront than to face uncomfortable heartbreak down the road.
You can preface the question with a light disclaimer to soften the approach, but I firmly believe this is one of the most important questions to ask. If your views on marriage and children don’t align, it’s better to know early on—you might be better off as friends or just “someone I went on a first date with.”
Question 8
Are you religious?
Religion is an incredibly personal aspect of life, and each individual brings their own unique perspective to this question. Before asking, take a moment to reflect on how much importance religion holds in your own life.
When your date responds, listen attentively and respectfully, as it’s a sensitive topic. Use their answer to internally assess whether their perspective aligns with your own beliefs or values. Ultimately, the significance you place on this question will determine how much weight you give to their response.
Question 9
Describe your perfect day.
We all have expectations in life, and paying close attention to how your date answers this question can give you valuable insight into theirs. This information isn’t just helpful for getting to know them better—it could also come in handy for future occasions like birthdays or special celebrations.
By listening to their response, you’ll learn more about their hobbies, favorite activities, and even their preferences when it comes to food and drink. This question is a great way to uncover what brings them joy and connect on a deeper level.
Question 10
Have you tried the ‘Japanese Cube Test’?
I once went on a date where the guy started asking me random questions about deserts, horses, and storms. To this day, it remains one of my favourite dating memories. This little personality test is not only fun but also offers a glimpse into the soul of the person sitting across from you.
It’s engaging, lighthearted, and makes for a memorable conversation. Plus, analyzing their responses adds a personal touch that makes them feel seen and special. It’s a unique way to connect and spark deeper insight while having a good laugh together!
Question 11
Describe one of your ‘hot takes.’
Being a little controversial is never a bad thing—it keeps the conversation interesting! Knowing how someone disagrees with the general population can show if you might agree with them.
As they explain themselves, stay open-minded. This question often brings out passionate responses and offers insight into how they communicate when faced with disagreement. I firmly believe that a strong relationship, of any kind, isn’t solely built on love and trust but on how well conflict and disagreements are handled.
While this question isn’t foolproof, it serves as a small preview of their communication style and how they navigate differing opinions.
Question 12
Do you have a favourite childhood memory?
Question 13
Cats or dogs?
Not much needs to be said about this question—just listen carefully to whether they prefer cats or dogs! It’s a classic, and the answer might just unexpectedly reveal a lot about their personality. Whether they’re a dog lover, a cat enthusiast, or maybe even a pet-neutral, this question is sure to spark some fun conversation (and maybe even a playful debate). Plus, who doesn’t love talking about pets?
Question 14
Do you believe in ghosts?
It might seem a bit bonkers, slightly mad, and even a little silly, but trust me—this question will not disappoint. At some point, we all have to confront the idea of death, in one form or another. By asking this, you open the door to the classic debate: what happens after we die? It could also take a turn toward superstitions or religious beliefs.
Listen to your date’s response with an open mind—laugh a little, get a little deep, maybe even cry a bit—and enjoy the conversation! You might just uncover some surprisingly meaningful insights along the way.
Question 15
If an alien arrived on Earth and you had to explain this (make circular hand gestures to indicate everything), how would you describe it?
It’s definitely the most peculiar question on the list, but don’t brush it off just yet. Never underestimate the power of the cosmos—it will catch your date off guard and might even put them on the spot. Asking them to explain “existence” can reveal just how deeply they analyze the world around them, their thought patterns, and how they mentally rank the hierarchy of beings.
This question also frees the mind, so be ready to hear some truly interesting (and possibly wild) responses. Keep an open mind—it’s sure to spark a memorable conversation!