55 First Date Questions Clever Dating Questions To Make A Real Connection

You also want to learn as much as you can without overwhelming your date with questions or with stories of your own. If only you had a list of good first date questions to help you make the most of this foray into uncharted territory. Because even if you’re a veteran of the dating scene, it doesn’t hurt to prepare yourself by adding to your first date conversation toolbox. You can’t control everything. But you can control what comes out of your own mouth. The list of first date questions below can help you and your date get to know each other well enough to know whether a second date would be more fun than food poisoning.

Questions to Save for Later

Don’t forget, also, that this is a first date — not the last chance to uncover devastating secrets before walking down the aisle. So, take it easy, learn what you can without making things weird, and focus on making this encounter as enjoyable and entertaining as possible for both of you. Things to talk about on your first date do not include the following:

How your date voted in the last election and whether they could ever love someone who voted differentlyYour date’s credit rating and debt-to-income ratioWhether your date ever left someone at the altarWhether your date’s apartment complex has any vacanciesWhether or not your date wants kids and/or is fertileYour date’s weird fetishes and how that might complicate living togetherReally anything related to living together or being a couple

When you’re making your own list of questions to ask on a first date, ask yourself, “Might this question give the other person the impression that I’m already picturing us as a committed couple?” And if there’s no reason to go down that road, run (don’t walk) away from that question into the safer territory of the first date topics listed below. You’ll thank yourself later.

What to Expect from a First Date

Here are a few things you’ll want to find out during that critical first date:

Is this person a psychopath, and am I the latest target?Is this person taking advantage of me to get a free meal or to feel more desirable?Am I attracted to this person, and how deep does the attraction go? (body, mind, soul)Can I talk to this person about a variety of topics? And do I enjoy talking to and listening to this person?Does this person frequently bring up past relationships and the damage they inflicted?Can I see us having just as much fun (or even more fun) on a second date — without even touching?

If this is a person you’ll want to keep dating, and the interest is mutual, give your minds and souls a chance to get acquainted before you let your physical attraction steer the ship. If you don’t, there’s a pretty good chance you’ll miss out on important information about the other person. Let this first date be about learning whether you two could enjoy each other’s company even if touching were not allowed.

55 First Date Questions

Conversation Starter Questions to Ask on a First Date

Ask any of the following questions to get a great start on any first date conversation.

1. What’s one thing you’d love to do for a date? Find out in a jiffy what this person is into and what he or she does for fun, would like to try, or would like to do with you.
2. What do you like about where you live? Rather than ask specific questions about your date’s living situation, make the conversation more about what this person likes about that situation.
3. Do you celebrate your birthday? And if yes, how (and when is it)? And if no, does it annoy you when others do? If you have a future date within a week of that birthday, you’ll want to know whether this person would like to be told, “Happy Birthday” or would appreciate a small birthday gift.
4. What is something you’re good at? This is another chance to encourage your date to focus on positives. As a bonus, you get to learn something of this person’s innate abilities.
5. Name something you’d like to be better at than you are now. Rather than ask, “What are you terrible at?” invite your date to talk about an area in which they’d like to improve. This way, you focus more on your date’s self-awareness.
6. If you were going out to do something fun by yourself, what would you do? You want to know whether this person can enjoy his or her own company. This is also an opportunity to encourage your date to see the value in self-care.
7. Describe your perfect day — or at least a perfect morning. This is related to the question, “What would you love?” but you’re asking specifically how your date would describe one perfect day (or part of it).
8. Is there anything about your life that you want to change? You want to know whether your date is pondering serious changes for the near future, and what those changes would mean for you both.
9. Tell me about something you’ve accomplished that you’re proud of. Again, you’re focusing on the positive by encouraging your date to recall a meaningful accomplishment — one your date will probably enjoy talking about.
10. What’s your favorite season, and what do you love about it? Does your date look forward to winter snow, the color changes of autumn, the new leaves of spring, or the balmy heat of summer? What does this person love most about the climate you share?
11. Are you glad to live where you are, or is there someplace you’d like to move to? Aside from “What do you like about where you live?” you can ask whether your date is content to live there or leaning toward a different living situation.
12. What would you do if you had so much money you didn’t have to work? This is a variation on “What would you do if you won the lottery?” It’s good to know what your date would do under those circumstances. And be prepared to answer that question for yourself.

Best First Date Questions

There are so many things to talk about on a first date. How do you know which date questions will get you the biggest return in terms of both enjoyment and useful information?

1. What do you like to do in your free time? The answer to this question will say plenty about your date’s priorities and their general approach to life.
2. What do you do (your job/career), and what do you like about it? Maybe it’s not this person’s “dream job,” but it might share some important elements with it.
3. Are you a night owl or a morning person? And what does your date love about being a night owl or a morning person? Don’t make this about which is better. Make it about the bigger picture of what your date loves.
4. What activities do you enjoy? You could include things your date does only some of the time — to mix it up a bit or to work off nervous energy before doing something nerve-racking but necessary.
5. Are you an introvert, an extrovert, or can you be either one according to the needs of the moment (ambivert)? No answer to this question should be a deal-breaker; it’s just good to know what boosts and what sabotages your date’s energy levels.
6. Tell me about your family (parents, siblings, extended family, pets). Does your date enjoy talking about family — parents, siblings, grandparents, etc.? Is this a person whose eyes light up when you ask about their family, or is this a painful subject.
7. What is your closest relationship right now, and how has it helped you to become the person you are today? This doesn’t have to be a relationship your date has had since infancy, but it should be one that influences your date in the present.
8. Are you more of an indoors person or an outdoors person — or do you prefer both about equally? You’re not asking, “So, for which date would it be appropriate for me to ask you to go fishing / go on a nature hike / climb Mt. Everest together?” You just want to know whether your date likes the outdoors or prefers being surrounded by walls at least 80% of the time.
9. If you could go anywhere in the world, where would it be — and why? Not only is this a great conversation starter, but you might find that you and your date are both drawn to the same place — or to different places for the same reason.
10. Do you have a pet? If you don’t, would you ever want a pet, and if so, what kind? Say you have a cat you love, and your date is allergic. Or your date owns guinea pigs and lets them roam the apartment freely, leaving tiny missile-shaped gifts (and puddles) wherever they go. It’s good to know these things.

First Date Questions to Ask Her

1. Do you mind if a guy opens doors for you or pulls out your chair? You might open the door for anyone, regardless of their gender. If your date would prefer you didn’t open doors for her, though, respect that — but also try not to let the door close in her face.
2. Would you mind if I picked up the tab for both of us, or would you rather we each paid for our own food? You’re showing respect for your date by asking her this. Whatever she decides, if you honor her decision, it tells her your respect for her autonomy is more important to you than your self-image.
3. What are your favorite foods? And how would you react if someone made one of those foods for you — but forgot a crucial ingredient? With this question, you learn not only what foods your date enjoys but also whether she’s open to having those foods prepared for her — even if the person preparing it might not make it as well as her favorite restaurant.
4. Do you have friends that are guys, and what interests do you share with them? You might share some of those interests, and it’s important to know whether or not this person could be a good friend – especially if you both decide to keep the relationship at that level.
5. Do you like men’s cologne, or do you usually find it overpowering? Do you have a favorite scent? Whether or not you’re wearing cologne to this first date, the answer to this question is useful information. Maybe your date isn’t crazy about cologne, but she is drawn to certain scents (like citrus or the smell of woodsmoke and trees).
6. Do you like roller coasters — or camping — or paddling a canoe on a quiet lake, etc. (or anything you enjoy doing)? You want to know whether this person shares some of your interests. And it’s a good idea to get her views on roller coasters before you take her to a theme park (if that appeals to you both).
7. Do you enjoy having friendly discussions — or even debates — on controversial subjects? It makes sense for both of you to answer this question since men and women both are capable of civil, rational discourse. And both are also capable of the opposite.
8. What would be an ideal birthday gift from someone who really knew you? This is dangerously close to an “If we were a couple” question, but you can preface it with “This is just to get a sense of what you like…”
9. And as a regular (or more frequent) gift from a friend, would you rather get fresh flowers or something else — like a coffee or a piece of fruit? With this question, you’re trying to get a sense of whether your date would welcome regular small tokens of friendship or devotion or whether she’d see them as “smothering.”
10. What would you love to accomplish in the next three years? You especially want to know which accomplishments would mean the most to your date.11. Tell me about your dad. When was the last time you got to see him, and what did you do together? The way a woman sees her father will influence her perception of other men. It doesn’t mean she’ll assume all men are like her dad, but the quality of that relationship follows her all her life.

First Date Questions to Ask Him

1. Do you ever hold the door or pull out a chair for a woman? You want to know whether your date would let a door close in your face or whether he’d be over-eager to ensure you never have to touch a door with your own hands.
2. Would you be fine with me paying for my own food, or would you be offended by that? You could add that you’re ravenous and you don’t want to punish him for that. It could also be because the last guy you dated expected something from you after paying for your meal.
3. Where would you take me on a date if we were just going to talk (not to eat and not to get physical)? You want to know by the end of the first date whether you can talk to this guy and whether you’d like to spend at least another hour just talking to him — without food or physical contact getting in the way.
4. If I were to ask you whether I should do something different with my hair, would you think I was asking you a trick question? He might. Hair is a pretty personal thing. He gets points if he likes your hair the way it is but also trusts that whatever you do to your hair, it’ll look great on you.
5. Do you have dreams of retiring rich before you’re 50? Would you be angry with yourself if you’re not able to do so? You want to know that this guy has well-rounded (as well as positive) expectations and the readiness to do what he has to do to make something happen. If he’s obsessed with being rich, your relationship — wherever it goes — will always come in second (at best).
6. What are your views on credit cards? Useful? The devil’s currency? A bit o’ both? The answer to this one shouldn’t be a deal-breaker. Credit cards can be useful when used responsibly. They can also be dangerous.
7. Do you keep a journal? If yes, do you prefer journaling with pen and paper, by typing on your computer, or by tapping out entries using a phone app? This could be an opportunity to extol the benefits of journaling or to discuss the different ways journaling has made life better for you both.
8. Have you ever created something that made you proud? We are all born creators, and each has certain gifts that serve this universal calling. What has your date created that lights him up inside when he talks about it?
9. If you could have any view from your home or your office, what would it be? Some folks love a cityscape, others prefer a view of water and trees. What does your date love to see when he looks out his office or living room window?
10. Do you enjoy debating? What topics do you enjoy for this? You could also ask if it drives your date nuts when people play “devil’s advocate” — or if he enjoys the challenge.
11. Tell me about your mom. When was the last time you got to see her, and what did you do together? A man’s relationship with his mom colors his perception of other women from an early age. It doesn’t mean your date will see all women as variations on his mom, but how he treats his mother will tell you something of how he’s likely to treat you.

Funny First Date Questions

Want to keep the mood light and easy? More interested in getting laughs than collecting information? Try any of the following conversation starters for dates that begin and end on a fun, easy, flirty note. It doesn’t have to feel like work.

1. Are you comfortable with dating a coffee / wine / beer / iPhone snob? If you’re any of these things — or a different kind of snob — and you can laugh at yourself, you’ll also be giving your date a heads-up that you have high standards for the object of your snobbery, but that you don’t expect others to share your obsession.
2. Do you dress up for Halloween? Or do you enjoy wearing costumes or cosplay outfits? Does your date enjoy dressing up as characters they admire — and do you share any favorites? Do you detect a shared fandom?
3. Have you ever fantasized about being a superhero? And what would be your top three superpowers, if you could choose them? Enough said.
4. If you could have one thing that would be a pain in the a-double-scribble to move from one home to another, what would it be? This could be a robotics lab, a life-size TARDIS made of Legos, a grand piano, a labyrinth of flowering plants, a rooftop garden, etc.
5. If you had to choose between living in a treehouse, a subterranean palace, or a houseboat, what would you choose? And if you could modify it in some way, how would you? Maybe you’re thinking of a treehouse designed by elves (Tolkien elves, not the ones from the North Pole) or a houseboat that makes the Titanic look cheap.
6. If you could be a non-human animal for a day, what would you be? This could also be a mythical creature or an alien life form.
7. If you could walk right now into your favorite store and buy something to enjoy in the present — without bothering to look at the price tag — what would it be? Be prepared to share your own dream splurge, too: a boat, the tent of your dreams, a Nespresso machine, a trampoline, that mattress set that costs as much as your rent (or twice that), etc.
8. What is your most frequent or most memorable weird dream? Whether your weird dream revolves around naked speeches or other people’s toilets, be vulnerable on this one. Everyone has weird dreams now and then.
9. Tell me about an embarrassing mistake and what you learned from it. The more embarrassing, the better. And don’t forget to laugh at yourself.
10. What did other people hate about your first car? And what did you like about it? Maybe your brothers hated your first car because it was made in a country where the mechanics make minor repairs either by telepathy or by routinely remove the entire engine. Or maybe it’s something else.
11. Marvel or DC? And can we still be friends if we choose different comic universes? And can you still be friends if one or the other has no love for either comic universe? You could also use this as a launchpad to discuss other fandoms.

Best Case Scenario

First of all, you don’t die. Secondly, you both enjoy the date, and you’re thinking, “This was fun! I’m looking forward to a second date!” Thirdly, that interest in a second date is mutual, and you don’t even have to touch each other to know that the attraction is real and goes beyond what you both see on the surface. If this is how your first date ends, congratulations! If, however, the interest in a second date is either not mutual or nonexistent, as long as you both survive it, you can learn from that experience and up your game for the next first date.

Wrapping It Up

Dating can be a minefield. The date questions listed in this article will enable you to see where those mines are buried, so you can avoid stepping on them. But dating isn’t just about not stepping on something messy or explosive. It’s about communicating and getting to know the other person a bit better, so you can both decide where you’ll go from there. Knowing which questions to ask a date – and when – will serve you well, not only for the first date but for any that come after it.

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