Mascara? Check! Perfume? Check! Branded jacket? Check! High heels? Check! Yes, we all know that the first impression is the last impression and that you would not leave a single stone unturned to come across as a charmer on your first date. But there is much more to us beyond the clothes and make-up; if you manage to connect with a person on the first date, you know you’ve bagged a second one.
So, what do you need to do to know a person better on the first date? Simple! Just ask the right first date questions. And don’t worry about them either because we are here to help you. We understand the value of getting it right in the first go. As Charles R. Swindoll said, “First impressions never have a second chance.”
Your mind is probably occupied with conversation starters and the first-date questions that you can ask. Do you need some science-backed questions? Or is your date totally into movies? Maybe you want to show off your sports trivia!
I guess you can do all of that quite smoothly. But…if you take our advice, there’s another path to winning hearts. Instead of getting into conversations on science, sports and movies immediately, you should concentrate on a few generic first date questions that will help you know your date better. The rest can follow after you’ve covered your basics.
How Do You Get To Know Someone On A Date?
On a first date, both of you are cautious and choose your words very carefully. Of course, the prescribed dating etiquette is followed religiously. You try to portray your best self in front of each other. But in trying to be perfect, you miss out on a world of fun. Treading lightly becomes very restrictive – how will you get to know the person on a deeper level?
Now, I know that connecting with someone on the first date isn’t an easy task. You don’t want to come off as clingy or intrusive, right? Asking too many questions might scare them away or make you look like a weirdo. So what’s the way to the sweet spot between creepy and thoughtful?
The first thing to do is ‘walk the talk’. Show your date the real you and put them at ease. When you are your most authentic self, others feel comfortable enough to do the same. It is a two-way street; show the person who you are, and they will let their guard down. When they see that you are honest and genuine, it fetches you brownie points, and they start opening up to you as well.
The second thing to do is the two-pronged activity of A-&-L (Ask & Listen). The former means asking questions that help you know your date better, while the latter refers to listening intently. A-&-L helps you learn so many interesting things, and it gives a pretty good vibe off of you. In a world where most people jabber incessantly, make a mark by listening well in your relationships.
25 Good Questions To Get To Know Someone On A First Date
So, how do you get to know someone better on a first date? Whether it’s an online or an offline date, starting a conversation on a first date does require some skill. And once you start talking, you need to make the best of it. A botched chat can damage your connection very quickly.
In a manner, asking questions is also playing it safe. You allow the other person to do the talking while still being in charge of the conversation. Shall we proceed to master the A-&-L approach? Here are the best first date questions to get to know someone better.
Related Reading: First Date Nerves – 12 Tips To Help You Ace It
Funny First Date Questions
Girls love men who make them laugh. They remember your jokes even when you’re not with them. In fact, a study reported that humor played a key role in sexual selection for women. But let’s not forget that men love to share a laugh too. Here are some science-backed questions to ask on a first date!
1. What is the cheesiest pickup line someone has used on you?
“Do I know you? Cause you look a lot like my next girlfriend/boyfriend.” Girls hate cheesy pickup lines, especially on first dates. But it is something they remember to share with their friends and laugh at. Talking about cheesy pickup lines like these can get you both talking about your worst dates. And that’s a hilarious way to bond.
Yes, you can go ahead and talk about the girl whose false eyelashes came off or the guy who wasn’t willing to pay his share of the bill on a date. Laughing about past idiocies can break any tension that’s present. You’ll get out of the ‘formal-mode’ and get comfy in each other’s company with these best ever first date questions.
2. What has been your most embarrassing moment?
Everybody has an embarrassing moment that they could put in perspective and laugh about. For instance, mine was when I broke a plate at a 5-star restaurant. The place was too posh to be real; the resounding crash of my plate, the pricey pasta on the floor, and the eyes of the whole crowd on me. They were aghast as if I had let an alligator loose in the restaurant.
When you two will get past the weird and embarrassing things you’ve done, things will be lighter and intimate. You can talk about stuff like dancing in a public elevator, drunk-dialing your ex, hangover stories, and so on. The possibilities are truly endless with this question.
3. What’s the worst thing you’ve done when you were bored?
When we are bored, we get the craziest of ideas and go forward with them. One of my friends dyed her hair yellow just because she was bored. Needless to say, she looked like a sunflower gone wrong. This is a stellar ice-breaker question for dating because it broadens the scope of the conversation. The best first-date questions are the ones that fish out interesting stories about your date.
4. What is the wildest thing on your bucket list?
Your hunt for interesting first-date questions ends here. All of us have a wishlist filled with the most absurd and entertaining items. Some of us want to travel to that exotic island, while others want to get their butt tattooed. Asking your date about their kookiest bucket list item can spark a line of conversation that is equal parts amusing and equal parts enlightening.
5. If you could be any celebrity for a day, which one would you choose?
The answers to this one are bound to crack you up. Maybe your date is interested in living life as a Kardashian, or maybe they want to walk a mile in Brad Pitt’s shoes. Witty fantasy-based questions like these are perfect to loosen things up a little. Always remember to not go in for a first date with an agenda.
Just have a good time organically. In a nutshell, don’t rehearse questions or lines. For all the men reading this, don’t try too hard to impress a girl on a date. Be as cool as a cucumber!
6. Would you rather live in a chocolate factory or a planetarium?
I’ve often thought that the best ever first date questions are ‘would you rather’ ones. Take this one for instance, the conversation could literally go anywhere. You might learn how your date is a sweet tooth, or you might discover their nerdiness and love for science fiction. Out-of-the-box questions are really here to save the day.
Related Reading: 50 Best Speed Dating Questions To Start A Conversation
Deep First Date Questions
When you really connect with someone and it’s going well, don’t shy away from asking meaningful questions. These will show them that you are interested in knowing them below the surface level. Here are some of the best first date questions to intensify the conversation.
7. Which parent is closer to you and why?
Now this question is a simple yet effective way of knowing whether your date has any mommy/daddy issues. Knowing which parent is closer to your date will give you a better insight when you butter them up in the future.
And it’s no secret that the relationships we share with our parents determine our attachment styles. Our childhood and formative years are vital in shaping us. When you learn about your date’s family, you will garner an understanding of how they may function in a relationship. And all good first date questions strive to accomplish the same.
8. Have you ever felt that everyone around you is a stranger?
There are a thousand instances when we’ve felt this way but might have never shared it with anyone else. Your date might have many friends but only a few would know their core. Asking this question will show them that you value authenticity.
Take this opportunity to share a few personal stories of yours too. Give and take are necessary to ensure a healthy flow of conversation. But when you breach personal subjects, be cognizant of setting emotional boundaries. First-date topics like these require a certain level of delicacy.
9. What is your biggest regret in life?
Who doesn’t have regrets? As relatable as it is, this question could go two ways. Asking about regrets may open a can of worms or may make them open up to you. They might begin to confide in you and which will give you pointers for your future dates with them (don’t expect them to spill the beans on the very first date).
You will also understand their emotional side better with this question. We are all shaped by our experiences in life and knowing the same of your date’s past can be a window to their soul. If they are not comfortable with any topic, don’t push it. Never feel entitled to any information regarding their life or previous relationships. After all, this is just a first date.
10. What are you most grateful for?
This sweet and simple question will turn the conversation to a serious note without putting a damper on the mood. You will liven up your date’s spirits by reminding them what they value in their life. And this revelation will be a very integral part of their story. I love such questions that help you know your date better. In the words of Kristin Armstrong, “When we focus on our gratitude, the tide of disappointment goes out and the tide of love rushes in.”
Related Reading: 51 Deep Relationship Questions To Ask For A Better Love Life
11. Who’s the most important person in your life?
An important part of our identity is shaped by the people we surround ourselves with. Our inner circle, especially, enriches our life deeply. Asking after the important people in your date’s life is a very wonderful thing. They will be touched by your gesture immediately. Be sure to actually listen to them after asking such good first-date questions.
Awkward First Date Questions
If you didn’t know yet, there’s such a thing as awkward first date questions. Awkward first-date questions are usually asked when you pick a time to make your date feel awkward and they end up telling the truth because their mind can’t think fast enough. These interesting first-date questions are a super-sneaky way of getting to know someone.
12. So, am I the same kind of person you thought I would be?
This is an easy and smooth way to ask about how you performed on the date. It’s like a sugar-coated technique of asking for feedback. You’ll be able to know how you fared from their reaction to this question. Awkward as they are, these are good first-date questions because of the results they yield.
For example, if the person thinks too much before answering, you’ll have caught them in a lie. However, if that person answers instantly with a smile, it’s likely that the date went well (you can start brainstorming second date ideas). As a matter of fact, you’ll also be able to tell if their answer is rehearsed. Aren’t these the best first-date questions?
13. Why are you still single?
This question will catch them at the moment (but there is a chance that it could prick them a bit.) If the person gets offended, you can cover it up by saying that they are attractive, smart and that any person would be lucky to have them.
This will cool them down, and they will feel a bit flattered as well. After the awkward phase passes, they might even open up about their past which will help you understand them better. However, you should be prepared with an answer too because they might ask you the same question.
14. Do you think that monogamy is possible in the 21st century?
If you are someone who is looking for exclusivity in a relationship, this question will get you your answers. The individual might feel a bit weird and awkward about you being so upfront on the first date itself, but isn’t this meeting the basis of future dates? It’s better to clear things out on the first date itself instead of finding out that the entire thing was a waste of time and emotions. If you both feel comfortable, you can get into a discussion on open relationships, polyamory and the likes.
Related Reading: Waiters Share Five Of The Worst First Date Stories They’ve Seen
Flirty First Date Questions
If the date is really going well and you both can spot the mutual attraction signs, there’s no bother in teasing each other with some harmless flirting. Only asking deep philosophical questions can bore them to death. Keeping things feisty is important; people don’t go on first dates to listen to sermons.
15. What’s the thing you liked most about me?
A bit of harmless flirting on a first date isn’t too bad. It depends on the kind of person you’re dating. However, your date won’t mind you asking about what they like most about you. If they tease you back, saying that they want to keep it a secret or build suspense, it means that they’re playing along. Flirty first-date questions like these help in building more curiosity and sexual tension between you two.
16. According to you, what is the biggest turn-on?
If they weren’t thinking about anything sexual with you, this will definitely do the needful. Ask them what their biggest turn-on is with a light touch on the hand. You’ll have sparks flying all over the place with your sizzling chemistry.
This is a great way of putting yourself into their head. (No better way of making someone think about you.) When they will start answering your question, they’ll think about their biggest turn-ons and imagine themselves with you. Can you feel the magnetic attraction? This one tops the list of interesting first-date questions.
17. Are you one for pillow-talk or cuddling?
Evaluate the way things are going before you ask this naughty question. Both the mentioned activities are things couples do after sex. You might come across as smug and cocky for presuming things…or you might make them blush. This is a great question to ask in a relatively intimate setting like a walk in the park. Maybe follow it up with a kiss if it feels like the right thing to do.
Related Reading: These 15 Subtle Signs Of Flirting May Come As Surprise To You
18. If you spent the entire day with me, what would you do?
This flirtatious question will make their heart stop for a second and make them think of a possible future. It will also help you analyze how well the date is going. If they talk about a friendly activity like going to a movie, shopping or going to a café, it means that they still see you as a friend or an acquaintance.
But if they describe something more intimate, like a candlelight dinner, it means that the date was a success. When they’ve got romantic indoor date ideas running through their mind, you’re doing a phenomenal job.
19. Has someone told you how lovely you are?
At times, you have to knock it out of the park with rhetorical questions. Your date will literally never see it coming, and you will render them speechless. What could be the answer to these best ever first-date questions? Just watch them struggle with the compliment pleasurably. From this point onward, you both will enter the sweet, sappy, and mushy zone of romance. You can thank me later.
Interesting First Date Questions – Rapid Fire
There’s no better way of keeping your date on their toes. And you’ll be surprised at some of the things a rapid-fire round reveals. The answers to these questions can lead to interesting debates and playful arguments because these first-date topics are unbeatable. In fact, these resemble speed-dating questions to a large extent. Are you ready to take things up a notch? Let’s go!
20. Edison or Tesla?
If you are looking for a science-backed question to ask on a first date, then this is it. If the answer is Edison, then they follow the herd. But in case it’s Tesla, it could mean that they have a mind of their own. Be sure to ask for the reasoning behind their choice to get a peek into their thought process as far as science goes.
21. Mask or no mask?
In the post-COVID world, there are two kinds of people. The first are those who have taken to the mask-like it is their second skin. And then you have the reluctant lot who wear it because they have to. They aren’t really comfortable in it and are on the lookout for opportunities to pull it below their chin. What an intriguing and novel question!
22. Fiction or nonfiction?
This is a fun question. Some people love fiction to a crazy extent. They can’t wait to lay their hands on anything that qualifies as a story. No genre is beyond the purview of their interest – classics, gothic fic, manga, fantasy series, etc. But there are others who stand in stark contrast to these fiction nerds. They love non-fiction and fact-based literature. What’s your date’s favoirte? Find out and have a fun discussion.
23. Pets or no pets?
Maybe you’re an animal person and your date is not. Perhaps you disagree on who’s better between cats and dogs. Maybe you’re a hardcore non-vegetarian and they are a vegan who supports PETA. Will you not come to us for second-date questions? Or do opposites attract? You tell us after asking these questions that help you know your date better.
24. Vegan or non vegan?
This is vital. If you are going to be dating them, then food is a big part of your relationship. Differences in diet can be a point of contention even if this sounds silly. If you both prefer the same kinds of food, then nothing like it. Having a foodie partner is the BEST! But if not, then there could be some adjustments you both will have to make.
25. OTT or theatre ?
In the present scenario where OTTs rule – would your date want to Netflix and chill or would they be game to drive to a theatre? Best ever first date questions like these will give you an idea if they are a homebody or a sociable person.
For many people, second dates turn out better than their first. This is because first dates are more about breaking the ice and getting past all that awkwardness. If your date asks you out again, voila! Getting to know someone isn’t a one-date job. However, these first date questions will give you pointers for future dates with them and you’ll get to know them more.