55 questions for a new relationship to deepen connection

There’s something so exciting yet terrifying about having a new relationship.

Exciting because you’re learning about a new person! And terrifying because, well, you’re learning about a new person and that person is also learning about you.

But sometimes, you just don’t know what to say.

So, here: A list of 55 new couple questions that you can use or adapt for conversations. Take what you think will work and leave what won’t, you still know your situation best.

Ready? Let’s go.

Brand New Boo

Okay, listen, this is important:

Before you take any of these questions, ask yourself, “Would I want to answer these?” It will feel less like an interrogation and more like a conversation if you’re also willing to answer them, especially for a brand new boo. 

The point of all of these is to find out more about your partner or potential partner, whichever stage you might be in. Proceed with every question with genuine interest, care, and respect for your partner.

Cool? Cool. 

1) Can you rank the five main love languages in order of what’s important to you?

This is vital information and it’s not too deep of a question even for a very new relationship. In case you’re not aware, the five love languages are: Acts of Service, Receiving Gifts, Quality Time, Words of Affirmation, and Physical Touch. It’s so important to know what makes another person feel loved and appreciated. 

Ranking the love languages instead of just choosing one can make for a lengthier conversation. Alternatively, you can ask about their “giving” and “receiving” love language instead. Do they show love by giving gifts but feel loved when you run an errand for them? Discuss.

2) What’s your weirdest habit?

Okay, this one is something you can just find out but it’s so interesting to know what someone considers their weirdest habit. 

3) What’s your biggest pet peeve?

Chewing loudly? Walking slowly? Interrupting someone while they’re talking? Minor annoyances like pet peeves can be the thing that sets off something bigger, it’s helpful to know these early on.

4) If you could only eat one thing for the rest of your life, what would it be?

You learn so much about people when they talk about their food preferences. This question is an exaggeration but it’s bound to give interesting results, no matter how wacky or simple the answer may be. 

5) What’s your specialty when it comes to cooking?

There are two ways this could go, either: 1.) They tell you the best meal they can make, or 2.) You find out that they can’t cook. Depending on what you value in a companion, this can be a minor or a major detail. 

6) What was your last big purchase? 

With this question, you can tell what people consider a big purchase, which connects to the next question. And that is:

7) What will you never spend any money on?

They could be the type of person to not spend money on coffee or has zero care about designer and luxury items. Perhaps they also never buy anything brand new or would never buy water at the airport. Do they not pay for streaming? Is popcorn off-limits? This question and the one above are opposing extremes but it gives you quite a range of green and red flags when it comes to finances. (And finances are a major stressor in relationships so it’s better to know early on.)

8) How do you handle a stressful day?

We all handle stress differently and it’s important to know if a partner or potential partner has healthy ways to decompress as built-up stress can cause friction. 

9) What is your #1 travel destination? Why? 

Traveling is one of those shared interests that can affect a relationship, for some it might even be a deal-breaker, so this question can certainly open that line of discussion. Do they travel for food and culture or just the nightlife? Do they want to visit tropical countries? Do they like to hike? Do they travel in style? Do they not want to travel at all?

10) How often do you use social media? 

How people use (or do not use) social media can say a lot about a person, including any red flags these might raise.

11) What’s #1 on your bucket list?

Bucket lists are just good conversation starters in general, what more for their #1? The first on this list could show you their strongest motivation or desire in life.

12) Are you a dog or cat person? 

Even if they’re neither a cat nor a dog person, they would at least have an opinion on pets. You can follow up by asking if they currently have any and if they do, ask for photos. I personally have yet to meet a pet owner who wasn’t ready to show off their pets, have you?

13) If you could change 1 thing from the last 24 hours, what would it be?

A bit more interesting than “How was your day?” And less heavy than “If there’s 1 thing in your life you wish you could change, what would it be?” 

14) Give me one good thing you’re proud of today.

Similar to the one above, it’s a loaded enough question that can start a discussion but it’s not as intrusive as What are you the proudest about yourself? Small steps, you know? 

15) What’s your most played song at the moment?

Music is an easy way to connect with someone. Music is one of those things that people can have very strong opinions about as our music choices are very personal.

16) What do you do when you’re bored?

What takes them out of their slump? Or do they just sleep the day away? Do you have common activities? Do they have a habit they do when they start to feel bored? 

17) Which one is easier for you to remember? Names or faces?

I, for one, never forget a face but names just don’t stick and that made for some funnily awkward situations. If you have stories you can share, swapping them could make for a hilarious conversation. 

18) Describe your perfect day. 

Ask them what they classify as a “perfect day” and what exactly it includes. Ask them to describe how it starts and how it ends. Ask them to include the things they will do. Does the weather matter? Does the place matter? Ask them to describe this to you in detail.

Getting Cozy 

So maybe you’re more comfortable around this person. Conversations are getting deeper, getting cozier with topics. You can talk about your childhood and it won’t be a complete landmine (as some childhood reminiscing can sometimes go.) 

So here are a few more questions:

19) How different are you from what you thought you’d be as a child?

This question could lead to deep conversations, it can bring up dreams, frustrations, triumphs, and sadness. Nostalgia is very powerful, proceed with care and understanding.  

20) Are you religious?

To be honest, this is something you can ask from the get-go, but depending on the person, this could be a very loaded question. Proceed respectfully. 

21) What’s your most controversial take on politics?

Similar to religion, talks on politics could be quite heavy and heated, but it’s often vital to know similarities or differences. Differences in political opinions don’t always end up as deal-breakers, that still depends on each person but like with religion, it’s important to approach this conversation respectfully and with an open mind.

22) How do you handle jealousy?

Jealousy is one of those things that catch you off guard in a relationship. Sometimes,

even someone who claims to not be a jealous person still feels it from time to time. Knowing how a new partner handles jealousy can give you an idea for down the road. 

23) What’s your definition of success?

Success is different for everybody and this means, two people can have very different paths and outlooks in life. Someone’s success might just be a quiet and simple life, while another might look like fame and riches. Knowing similarities and differences early on can save your frustrations in the long run. (There will be a similar question down this list, but both are equally important.) 

24) If your friends would introduce or explain who you are to a stranger, what would they say?

This question will give you a little bit of insight into your partner’s friendships: Are they a fun bunch? Serious? Have they been friends forever? 

25) How do you want people to remember you?

Do they want to be remembered as kind? A good friend? Do they want the world to remember them by the work they will leave behind? This question is a definite thinker. 

26) Describe your most recent ex in 100 words or less.

You can tell a lot about a person by how they talk about their previous relationships. Do they villainize every person they’ve ever been with or do they talk about past relationships with respect and civility? Not that I’m making you overthink but if things don’t work out between the two of you, you could be the person he’s going to discuss with their new partner in the future.

27) How did you survive your first heartbreak?

First heartbreaks could be life-changing for some, it’s your first time experiencing a failed relationship after all. Ask how they coped or if they thought they would never love again. You could also ask them what they learned and how it changed them as a person. 

If someone has never experienced heartbreak before, ask them what they think they will do if they ever experience it. 

28) Your best birthday celebration. Describe it to me.

When was it? What made it special? Who made it special? As birthday celebrations are personal, it’s nice to know what a person values for their special day. If they’re the type of person who doesn’t like celebrating their birthday, you can then ask them why they don’t. You can also ask this question either for previous birthdays or future birthdays. 

29) What’s the best gift you’ve ever received? What made it special?

Better take extra notes on this part. 

30) Describe your mom in 100 words or less.*

Similar to how a person talks about their ex, it’s also important to know how they talk about their mom, mother figure, or primary caregiver. Do they talk about them with love and respect? Animosity? Without care? With nostalgia? It’s a very telling question, so proceed with respect and an open mind. 

* If the question doesn’t apply, you can ask about their closest family member instead.

31) Name your biggest fear.

Knowing someone’s biggest fear can sometimes lead you to know what their main motivations are. Fear sometimes motivates people but it could also just make them run away from giant spiders. 

32) Do you think you give good advice?

If they say yes, try asking them when was the last time someone asked them for advice and what for. If they say no, ask them why. Additionally, you can ask them who they come to when they need advice as well. 

33) Have you ever written a love letter before?

If you’re a fellow romantic, you will agree that love letters are sweet and endearing. It’s such a lost gesture that it’s surprising to find ones who still write them. If they answer Yes, try asking them what they felt while writing the letter and if they say no, ask them if they think they ever will. 

34) How different am I from your first impression of me?

First, you ask them about their first impressions of you and then how similar or different you are from their guess. After all, first impressions are important but getting to know people past that first impression is even more so. 

35) What do you think about Valentine’s Day?

For some, Valentine’s Day is an important celebration; for others, it’s just a normal day. Possible follow-up question: How do you celebrate Valentine’s? Or What’s your ideal Valentine’s date?

36) Who was your childhood hero?

Depending on their answer, you can also ask them if they have met this person. If their answer is more personal (like a family member or an old teacher, etc.), ask them exactly what made this person their hero. 

37) What’s the meaning behind your name?

Were they named after their parents? After a song? A celebrity? An ancestor? Are they using a name they chose themselves? Stories about people’s names are always so interesting, sometimes even funny. 

38) When was the last time you cried? What was it about?

Vulnerability is difficult a lot of times and everyone is going through things we know nothing about, so proceed with this question with care and understanding. 

39) What’s your idea of a perfect date?

You better be taking notes here. 

For real

I truly, truly believe in not putting unnecessary pressure on myself or my partner. Note the word “unnecessary” as some pressure is necessary for growth. If you see this relationship going favorably, here are some more questions to see if this could be for real:

40) Are you looking for something long-term?

Imagine this: You find this person as someone you wish to date long-term only for them to tell you they aren’t ready for that. Or worse, they weren’t even looking for that at all. 

It’s better to ask this question when the relationship is fairly new, communicating what you want or looking for in a relationship lessens misunderstandings. (Communicating and listening are vital in relationships in general. Use them well.)

41) What’s a non-sexual act that turns you on?

Whenever I ask this question to someone, be it a potential partner or a friend, it always produces interesting answers. It could be as simple as someone running their hand through their hair or something as far away from sexy such as using correct punctuation marks. This would make for such a fun conversation and you could even ask this in list form!

42) What’s 1 thing you wish we did more of during sex?

Communicating needs and desires regarding sex is still a difficult conversation for some people but it shouldn’t be. As long as everything remains consensual, it will allow for partners to enjoy the experience more as they are having their needs and desires met. 

43) Do you see yourself getting married?

Is marriage in the cards for them? Do they not want to get married at all? Are their opinions set in stone? Marriage is a deal-breaker for a lot of people so making sure where both of you stand on this topic could be helpful. 

44) Do you see yourself having kids?

Similar to the question above, the topic of having kids could also be a deal-breaker for people, it’s a life-changing decision after all. 

45) Define “cheating”

There are times that people consider emotional cheating as worse than physically cheating on someone. Flirting with other people? Could be. It really depends on the person. And with that said, the next question is:

46) Have you ever been unfaithful before? If yes, why?

In this question, I urge you to put your thinking cap on, especially if they said Yes. Would they be giving you a bunch of excuses? Have they reflected and repented? Reason and frequency should also be asked here.

Sure, not everyone will answer this openly and honestly but better ask than not.

47) What do you think relationships should have more of? Less of?

Most of us have an idea about The Perfect Relationship, you might want someone who is close to their family and yours. You might want someone who surprises you with gifts often, someone who is very sexually compatible. You might want your relationship to have fewer arguments and more understanding. More times saying I love you? Should relationships have more trips together? 

48) What’s the best thing you love about our relationship?

Celebrate what’s going right in your relationship. Once you know what their best thing is, ask them why they think so. Also talk about other things you love about your relationship, from the smallest gestures to the grandest. 

49) What’s your least favorite thing about our relationship?

In the same breath, talking about your least favorite things about your relationship is not an attack but rather a point for improvement. It’s better to address these things as soon as possible rather than letting them weigh you down and even potentially ruin you as a couple.

50) What would make you hate someone?

Hate is such a strong emotion that there usually are definite reasons behind people feeling so. Their answers could also define their strong boundaries, the limits of their patience and tolerance, which is always good to know. 

51) What’s one question you’re too shy to ask me?

I recommend NOT starting with this question but rather sandwiching it between others. (There’s a reason they were shy after all.) If they still refuse to ask you a question, then it could mean they’re still not as comfortable to do so and you can shelf this question for another time. 

52) Have you ever been in a long-distance relationship? If so, what happened?

Not everyone is equipped or even willing to be in a long-distance relationship, for some this could even be a deal-breaker. 

53) What’s one decision you wish you could change?

This question is about regrets, which could lead to a whopper of a conversation if you’re both ready to ask and answer. As I’ve been repeating in this article, proceed with care and understanding.

54) Do you forgive easily?

Or are they the type to hold grudges? Is forgiving and forgetting more their style? What will it take for them to forgive someone? Forgiveness is a very vulnerable topic and could bring up unpleasant memories so continue with (you guessed it) care and understanding. 

55)What is “happiness” for you?

For my final question for this list, let’s talk about happiness. I separated this question from the question about success because sometimes those two things are not the same for one person, perhaps one is even more valued than the other. 

Each person defines happiness differently, what should be in your life before you consider yourself happy? 

What needs to happen before you can say, Yes, I’m happy? Does it include a stable job? What about a loving partner? Perhaps happiness means a life free of worry. Or maybe their definition includes endless wealth and fame. Whatever they may be, it’s bound to be a very fruitful conversation. 

So, what now?

My list might be ending here (for now, wink wink) but I sure hope you took what resonates with you. 

Navigating relationships isn’t easy to begin with but especially new ones, but you know what they say about solving problems, right? Identifying there is one is already the first step. You being here, looking for answers is more than a lot of people would be willing to do. I sure hope I gave you relationship questions that sparked inspiration and conversation.