You’re sitting across from him at dinner, and the conversation has hit one of those awkward pauses.
He’s nice enough. Attractive. Seemed interesting when you matched online or when your friend set you up.
But now you’re here, and you’re not quite sure what to ask that goes beyond “so… what do you do?”
First dates can feel like job interviews disguised as romance. You’re trying to figure out if this person is worth your time while also trying not to interrogate them like a detective solving a crime.
Here’s the thing: the questions you ask on a first date matter more than you think.
They’re not just conversation fillers – they’re windows into who this person really is, what they value, and whether you’re actually compatible or just killing time together.
You don’t need to grill him with heavy questions right off the bat, but you also don’t want to waste weeks on someone only to discover major incompatibilities that could’ve been spotted over appetizers.
The right questions strike a balance – interesting enough to go beyond small talk, revealing enough to give you real insight, but light enough to keep things comfortable and fun.
Think of this as your secret weapon for first dates. These questions will help you move past surface-level chitchat and actually figure out if there’s potential here or if you should cut your losses before dessert.
20 Questions to Ask on a First Date to Know If He’s Worth It
Icebreaker Questions
Start here when you’re both still settling in and finding your rhythm together. These questions are easy, non-threatening, and great for easing into deeper conversation.
1. How do you usually spend your weekends?
This simple question reveals so much more than it seems.
Is he constantly working?
Does he have hobbies and interests outside of his job?
Is he a homebody or more adventurous? Does he have friends he regularly spends time with, or does he seem isolated?
His answer gives you insight into his lifestyle, priorities, and what dating him might actually look like.
If he spends every weekend hiking and you’re a dedicated indoor enthusiast, that’s valuable information.
If his weekends revolve around drinking with buddies or gaming alone for 48 hours straight, you’ll want to know that upfront.
Pay attention to whether his weekend activities leave room for a relationship or if his life seems too packed (or too empty) to fit someone else in.
2. What’s your go-to comfort food?
Yes, this seems like a throwaway question, but food is personal and revealing.
His answer tells you about his background, his relationship with food, and even his emotional habits.
Does he cook for himself or rely entirely on takeout? Does he have childhood favorites tied to family traditions?
Is he adventurous with food or pretty basic in his tastes?
Plus, if things go well, you now know what to surprise him with later.
And if he’s weirdly judgmental about your comfort food choices, that’s also information worth having.
3. Are you more of a morning person or a night owl?
This might sound trivial, but lifestyle compatibility matters more than people realize.
If you’re someone who thrives on 5 AM workouts and early bedtimes, dating someone who doesn’t function until noon and stays up until 3 AM can create friction.
Or maybe you’re both night owls who can bond over late-night conversations and sleeping in on weekends.
Either way, understanding his natural rhythms helps you picture what daily life together might actually feel like.
4. What’s the last show you binge-watched?
This opens up conversation about entertainment preferences, how he spends downtime, and gives you potential common interests to explore.
Does he watch thoughtful dramas, mindless comedies, intense thrillers, or reality TV?
Is he someone who gets deeply invested in shows or just has them on as background noise?
You can also learn about his attention span and ability to commit to things (yes, even TV shows can be revealing).
Someone who starts dozens of shows but finishes none might have commitment issues in other areas too.
Fun & Flirty Questions
Once you’re both comfortable, these questions add playfulness while still revealing important compatibility factors.
5. What’s your idea of a perfect date?
This question serves double duty – it shows you what he values in romantic experiences AND gives you ideas if you end up planning future dates.
Does his perfect date involve expensive restaurants and fancy activities, or is he more low-key?
Is it adventurous and active, or relaxed and intimate? Does it involve other people or is it just the two of you?
Pay attention to whether his answer is generic or thoughtful. “Dinner and a movie” is fine, but something more specific and personal shows he’s actually thought about what creates connection and enjoyment for him.
6. What kind of things make you laugh the most?
Shared humor is underrated as a compatibility factor.
If you find completely different things funny, conversations might feel forced. If your humor overlaps, you’ve found one of the foundations of good chemistry.
His answer also reveals whether he has a sense of humor at all (some people genuinely don’t), what kind of comedy he appreciates, and whether he takes himself too seriously or can laugh at life’s absurdities.
Bonus: telling jokes or funny stories to each other naturally follows this question, which loosens things up and makes the date more enjoyable.
7. If we were to plan a spontaneous trip, where would we go?
This hypothetical question is playful and low-pressure while revealing his sense of adventure, travel interests, and spontaneity level.
Does he immediately have an answer or does he seem uncomfortable with the idea of spontaneity?
Is his answer somewhere nearby and practical, or wildly ambitious? Does he consider your interests in his answer or just his own preferences?
It’s also a subtle way to gauge his travel experience and whether he’s someone who makes things happen or just talks about “someday” without follow-through.
8. What’s something most people don’t know about you?
This invites him to share something personal without being too heavy or invasive.
Maybe he’s secretly great at painting. Maybe he speaks three languages. Maybe he’s terrified of birds.
Whatever he chooses to share shows you he’s comfortable being vulnerable and gives you insight into parts of himself that aren’t obvious on the surface.
How he answers this also matters – does he deflect with humor, share something genuinely interesting, or struggle to think of anything? All revealing.
Deep & Meaningful Questions
These questions help you move beyond fun banter into understanding who he really is and what drives him.
9. What are you most passionate about right now?
Passion reveals priority. This question shows you what truly matters to him beyond work and basic responsibilities.
Does he light up when talking about something specific, or does he struggle to identify anything he’s genuinely passionate about?
Is it creative, intellectual, physical, social? How does he pursue these passions?
Someone without passions or interests beyond work and routine might be perfectly nice but potentially boring long-term.
You want someone who’s engaged with life, not just going through the motions.
10. How do you usually handle stress or tough situations?
This is one of the most important questions you can ask because life will inevitably get stressful, and you need to know how he copes.
Does he shut down or open up? Does he become aggressive or withdrawn? Does he have healthy coping mechanisms or destructive ones?
Can he handle adversity without falling apart or lashing out?
You’re not looking for perfection here – everyone has their moments.
But his answer gives you a preview of what hard times together might look like, and whether he has the emotional maturity to navigate challenges.
11. What kind of people inspire you?
Who we admire reveals what we value.
Does he admire people for their character, accomplishments, creativity, kindness, intelligence?
Are the people who inspire him similar to who you respect and look up to, or completely different?
This question also shows whether he surrounds himself with people who push him to grow or whether he’s content staying stagnant.
12. What’s a goal you’re working on this year?
Goals reveal ambition, discipline, and self-awareness.
Does he have any goals at all? Are they specific and actionable, or vague wishes?
Is he actively working toward them or just talking about them?
Someone who sets and pursues goals – whether professional, personal, health-related, or creative – shows they’re intentional about their life.
Someone without any goals might be coasting, which could be a red flag depending on what you’re looking for.
Relationship & Values Questions
These questions get to the heart of compatibility around relationships, family, and how he shows up for people he cares about.
13. What does a healthy relationship look like to you?
This question is critical because it reveals his relationship blueprint.
Does his answer include communication, respect, partnership, and growth?
Or does he struggle to articulate what healthy relationships even look like, possibly because he hasn’t experienced many?
Listen for red flags like controlling behavior disguised as caring, or extremely independent attitudes that might mean he’s not actually ready for partnership.
14. Are you close to your family?
Family dynamics tell you a lot about someone’s attachment style, values, and potential relationship patterns.
You’re not looking for a perfect family here – nobody has that.
But understanding his family relationships gives context for how he relates to others, handles conflict, and what family might look like if you build one together.
Also pay attention to how he talks about his family. Respectful even when acknowledging imperfections?
Or bitter, dismissive, or overly idealized? All revealing.
15. How do you show affection to someone you care about?
This is basically asking about his love language without making it sound like you’re reading relationship books together on a first date.
Does he show affection through acts of service, words, physical touch, quality time, or gifts? Does his style align with what makes you feel loved?
Understanding this early helps you recognize his efforts to show care, even if they look different from what you’re expecting.
16. What’s your love language?
Okay, now you can directly ask about love languages since you’ve already warmed up to the topic.
If he’s familiar with the concept, great – you can have a meaningful conversation about how you both give and receive love.
If he’s never heard of it, you can explain briefly and see how he responds to self-reflection about relationships.
This question also shows whether he’s done any work understanding himself emotionally or if he’s completely new to thinking about relationships this deeply.
Quirky & Unexpected Questions
These lighten things back up while still giving you interesting insights into his personality and imagination.
17. If you could have dinner with any fictional character, who would it be?
This question reveals what stories and values resonate with him.
Does he choose someone wise, funny, adventurous, or complex? Can he explain why this character matters to him, showing depth and self-awareness?
Or does he blow off the question entirely, suggesting he either doesn’t engage with fiction or doesn’t take imaginative questions seriously?
It’s also just fun and gives you both a chance to geek out over books, movies, or shows you love.
18. What’s the weirdest food you’ve ever tried?
Food adventure stories are always entertaining and tell you about his openness to new experiences.
Has he traveled and tried local cuisines, or has he stayed within his comfort zone?
Is he judgmental about unfamiliar foods, or does he approach them with curiosity?
This question usually leads to funny stories and gives you both something to laugh about together.
19. If you could live anywhere for a year, where would you go?
This reveals wanderlust levels, cultural interests, and whether he’s tied to his current location or open to change and adventure.
His answer might also give you insight into whether his future plans are flexible or set in stone, which matters for long-term compatibility.
20. What’s something on your bucket list?
Bucket lists reveal dreams, priorities, and whether he’s someone who actively pursues experiences or just passively wishes for them.
Does he have a bucket list at all? Are the items on it achievable or completely unrealistic?
Does he talk about them as “someday” dreams or actual plans he’s working toward?
This question also gives you material for future date ideas if things progress.
Bonus Section: Questions to Avoid
Not every question is first date appropriate. Here’s what to steer clear of and why.
Don’t ask about exes. Nothing good comes from this on a first date. If he brings them up constantly, that’s information. But don’t directly ask about past relationships – it creates comparison energy and brings negative baggage into fresh connection.
Skip money questions. Asking about salary, debt, or financial specifics is too invasive for a first meeting. You can gauge financial responsibility through more subtle questions about goals and lifestyle without getting into actual numbers.
Avoid politics and religion initially. Unless these are absolute dealbreakers for you and you need to know immediately, save heavy political and religious discussions for when you’ve established some rapport. First dates should be about discovering compatibility, not debating ideologies.
Don’t interrogate about past trauma. Questions about childhood wounds, therapy topics, or painful experiences are too intense for first dates. If he volunteers this information, listen respectfully. But don’t dig into sensitive territory before trust is established.
Stay away from future pressure. Don’t ask about marriage timelines, how many kids he wants, or where he sees himself in five years. These conversations matter eventually, but on a first date they feel like pressure and expectation rather than genuine curiosity.
The goal is keeping things positive, interesting, and comfortable while still learning real information about who he is. You want to create connection, not conduct an investigation.
Pay attention to what feels natural in your specific conversation. Not every question needs to be asked, and not every answer needs to be perfect.
You’re looking for green flags, watching for red ones, and most importantly – seeing if there’s genuine chemistry and compatibility worth exploring further.