77 Questions For A New Relationship To Build A Deeper Connection

questions for a new relationship

Adam LoDolce

This article was written by a professional love strategist. If you want to learn the 7 Little Love Steps, click here.

Did you know that specific questions can help you get to know your partner more intimately in a new relationship? Whether you’ve been dating for a few weeks or months (or even years), there are questions you can ask each other to build your connection.

Dating should be a balance of having fun, getting to know each other, and figuring out whether you’re compatible for a long-term relationship (if that’s what you’re looking for). And one of the best ways to get to know your partner better and build an authentic foundation is to have deep, meaningful conversations. Conversations where you share your greatest passions, dreams, and goals, your most terrifying fears, embarrassing moments, regrets from the past, and more. You’ll start to uncover why your partner is the way they are, and vice versa.

These questions will require you both to be a little vulnerable and actively listen, empathize, and be honest. Some are a little heavier than others, but you’ll generally find a conversation like this incredibly insightful and a lot of fun!

The science behind the questions to ask in a new relationship

Social psychologist Arthur Aron conducted an experiment and found that pairs of people who discussed “deep questions” were more likely to maintain and grow their connection than those who only shared small talk.

Now, there’s no guarantee that these questions will help bring you closer together and build that all-important emotional attraction, but when have there ever been any guarantees when it comes to relationships? The simple act of opening up to each other can really help strengthen your bond.

And these questions aren’t limited to those in a new relationship. If you’ve been with your partner for a while, you can also use these questions to reconnect with each other, and you might find out something life-changing that you never knew!

77 questions for a new relationship to build a deeper connection

1. Tell me what you’re most grateful for right now?

The act of thinking about what you’re thankful for will put you both into an abundant mindset, and you’ll get to see what he appreciates most. It’s these little things that become the big things in life.

2. What does a “perfect” day look like to you?

Okay, so there’s no such thing as perfect, but there are days when it feels like you’ve gotten really close. This question will help you get a clearer picture of how he likes to spend his time day to day.

3. What do you like most about me?

This question can work no matter how recently you started dating. If you’ve only been on a few dates, then you’re likely to get a surface-level answer (e.g., you’re fun to be around, the way you laugh). But if you’ve been dating a while, he will probably share something that runs deeper.

4. What place in the world would you most like to go on vacation?

Get to know where he’s already traveled and the places on his future vacation list. Do you have any places you both want to explore? Maybe you can plan to go somewhere together soon!

5. What three things in your life could you not cope without?

It’s tough to choose just three, so this will give you a great sense of what he values most and what his priorities currently are.

6. Tell me something you’ve never told anyone before.

It’s up to him how deep he chooses to go with his answer. If he feels like it’s too soon to share a big secret with you, then he might have fun with his response by saying something like, “I’m terrified of peas.”

7. What initially attracted you to me?

couple hugging

Most guys will answer with something physical here—unless you were friends first and have known each other a while. Your great smile, your beautiful eyes, your quirky style, etc.

8. If you had to describe our relationship in three words, what would they be?

If you’ve already defined your relationship (Little Love Step #6), then this will tell you how your partnership feels to him.

9. What’s the greatest achievement of your life so far?

You may think you already know this, but perhaps what he sees as his greatest achievement and what you think is different. You’ll never know until you ask!

10. What’s at the top of your bucket list right now?

Even if he doesn’t have a physical bucket list that he’s written, there will likely be a bunch of things he wants to do and hasn’t found time to… yet. This will give you an insight into the new experiences he seeks.

11. Tell me about one of the most adventurous things you’ve done in your life so far?

Maybe he’s a conservative guy, or perhaps he’s an adrenaline junkie. This will give you an indication of where he sits on the spectrum and whether you share the same definition of adventure.

12. What do you value most in a relationship?

An essential question to ask someone you’re thinking of building a relationship with. What are they looking for?

13. What’s your relationship like with your parents?

Some of us are incredibly close to one or both of our parents, while others of us not so much. Others don’t even know their biological parents. This will alert you to any potential family issues or close bonds.

14. If you could wake up tomorrow with a new skill or talent or gift, what would you choose?

You can literally pick ANYTHING here. Wizardry, fortune-telling, juggling—the world is your oyster.

15. If you had an unlimited amount of money to start a business tomorrow, what would it be?

Maybe you’ll find out that he does have a business idea and wants to start a business eventually, or perhaps he already has one on the side.

16. How have you changed over the last five years?

Five years is a big chunk of time. It’s likely the man he is now is different in multiple ways. This will show you how he’s grown, what he’s learned, and where he’s striving to go.

17. What has been the most embarrassing moment of your life?

A brilliant question for a new relationship. We’ve all had our fair share of embarrassing incidents, but retelling them often puts us right back in the moment and turns our cheeks a deep shade of rouge!

18. If your house caught on fire, assuming all your loved ones are safe, what would you grab to save before you left?

Is he possession orientated? Is there anything in his house that means a lot to him that you don’t know about yet? Or would he be happy leaving everything, just as long as his loved ones were safe?

19. What’s something you’ve always wanted to have a go at trying but haven’t yet?

This can be anything—surfing, playing guitar, learning how to make pottery, ballet, singing karaoke, etc. Maybe you can make a plan to do it together (if you’re game)?

20. What would your perfect date with me look like?

If you’ve just started dating, this can be a fun question because he might just end up describing a beautiful date that he then takes you on very soon.

21. If you become a billionaire, what’s the first thing you would do?

A BILLION dollars is a lot of money. More than anyone needs. So, is he a saver, a spender, or a giver? What is his current relationship with money like?

22. What are three things you admire most about yourself?

I love this question because too many of us focus on what we’re not so great at while ignoring our amazing qualities and talents. This will make him feel really good about himself, and he will associate that feeling with you.

23. What are three things you admire most about me?

questions for a new relationship

Get ready to feel good about yourself too! It’s always nice to have an outward perspective on who you are and how others see you.

24. What did you love doing as a child that you don’t do anymore?

We all have hobbies, interests, and family traditions that we did all the time growing up but eventually grew out of or didn’t make time for. Maybe this question will lead him to pick up an old hobby he loved.

25. When was the last time you cried?

Men are known for having a lot of shame around showing their emotions, and we learn this from a very young age. Has he EVER cried (there are a rare few who haven’t—FYI, I am NOT one of them)?! If so, has he ever cried in front of anyone else?

26. What advice would you give your younger self?

Was there something he did or didn’t do growing up that he still regrets or feels frustrated about?

27. What has been the most significant happy accident in your life so far?

There are times in our life when something unexpected happens, and although it’s not what we wished for, it ends up being a tremendous blessing in disguise.

28. What does love mean to you?

Love means different things to all of us. Find out what it means to him and see if you’re on the same page.

29. How do you feel about marriage and kids? Do you see those things in your future?

This is an important question to ask any guy you’re dating because these are BIG lifestyle choices you need to align with for your relationship to work.

30. What’s your biggest fear?

Every human being has fears and phobias, no exceptions. Maybe he’ll say something common like rats, or perhaps he’ll surprise you.

31.Describe your perfect weekend to me.

Knowing how he prefers to spend his weekends is vital because if he loves to party while you prefer chilled, lazy weekends, you may clash.

32. Is there anything you’re afraid to ask me but have been wanting to for a while?

This question will put you in the hot seat, but it’s a great way to be vulnerable with him and bring your guard down a little.

33. When was the last time you did something out of your comfort zone? How did it make you feel?

Stepping out of your comfort zone is both uncomfortable and thrilling. Before you go for it, and sometimes in the moment, it can be scary. But afterward? It’s liberating.

Is he someone who regularly challenges himself, or does he tend to live life within self-imposed limits?

34. What is your favorite book of all time?

If he doesn’t read anymore, this can be a book he loved as a child. And if he’s coming up short here, feel free to switch “book” for “movie.”

35. Tell me about a recent dream you remember having.

Our dreams often seem crazy if and when we remember them the following morning. But did you know they are filled with messages from your subconscious?

Yes! Google what his dreams symbolize.

36. If you knew you only had a year left to live, how would you spend it?

We all know our time is limited, but too many of us live our lives as if it’s infinite. If it came down to 365 days, what would he do differently in his life? Maybe he wouldn’t change a thing. Maybe he would change everything.

37. How did you end up in your career, and do you ever think about doing anything else?

Many people fall into jobs by accident or see them as temporary but end up staying in those jobs for the rest of their lives. Is he happy with his career? Is he looking to make a change anytime soon? It’s never too late!

38. Have you ever struggled to love yourself?

We don’t talk about this enough, especially us guys. I know a ton of guys who have struggled with self-confidence, self-love, and mental health issues. Even if he appears to be super confident, there’s a chance he’s faking it or has struggled in the past.

39. If we broke up, what would be the thing you miss most about our relationship?

If you’re in a relationship with the guy in question, this will tell you the number one thing he loves about being with you and what your partnership adds to his life.

40. Do you know what your love language is?

questions for a new relationship

If you haven’t yet taken the test and figured out what your love language is, do it! When you know how you best receive love and affection and what you’re looking for from your partner, it can significantly improve your connection.


41. Tell me about a moment in your life you can point to and say, that’s when it all changed?

We all have those moments in our lives—sometimes they’re big, and other times they’re much smaller. And we may not realize it when they’re happening, but that event or choice changes the entire trajectory of the rest of our life.

42. Do you ever wish you could do something all over again?

Maybe there’s a stand-out day or experience he wants to repeat, or perhaps something didn’t quite work out the way he wanted it to, and he’d like a second chance.

43. Do you have happy memories of your childhood?

Some of us have wonderful memories of growing up, while others are not so fortunate. Either way, this will help you understand his psyche a little more.

44. What is one habit you would like to change but are struggling to?

We all have our vices or habits we’ve fallen into and struggle to break. Maybe he drinks 11 cups of coffee each day, or orders takeout a little too often, or can’t remember to put the toilet seat down after he’s done (even though he knows it drives you INSANE).

This is a great question for a new relationship because it tells you the level of habits you’re dealing with.

45. What’s your number one goal for this year?

Is he the kind of guy that thinks about and sets goals for himself? Or does he go with the flow and not tend to push himself or have any grand ambitions? Neither one is better. What’s important is that you’re content with the way he lives his life.

Editor’s note: Ready to attract higher quality men? Join Adam on this free webinar to discover the 3 steps to building emotional attraction

46. If you could swap lives with anyone for a day, who would you choose?

You can pick anyone here, past or present. I know it’s tough to choose just one person, but this will give you great insight.

47. What are you most excited about getting older?

For some reason, we are all terrified of getting older and try to avoid it at all costs. But aging is a beautiful, rewarding experience if you let it be.

48. Are you a giver, a taker, or a matcher? Take the test here!

Relationships require both of you to be giving equally to your relationship. Naturally, there will be times when this balance shifts, but generally, it should always feel like it’s equal.

49. When you picture your future, what do you see?

If a guy can talk about the future with you, this is a great sign. If he mentions similar things to what you see in your future, even better.

50. Do you believe we were destined to cross paths?

When it comes to questions to ask in a new relationship, this one helps you see whether he believes in things like destiny and fate or whether he’s adamant that he is 100% in control of his life.

51. What’s the biggest challenge you’ve faced and overcome in your life?

Challenges are tough while we’re working through them, but the act of doing this helps us grow and evolve as a person and become stronger than we were yesterday. Is he used to challenges, and does he welcome them?

52. What do you think is key to our relationship working so well?

Get him to open up to you on how he sees your partnership, how each of you shows up, and how you complement each other.

53. How would you like people to remember you when you’re gone?

One of the best questions to ask in a new relationship.

Why?

Because it will help you understand what’s important to him. Does he want to be known as someone who broke records, changed the world, or helped many people? Or is he simpler and content with being remembered as a friendly, loving soul?

54. Do you ever talk to yourself?

If the answer is yes, you may or may not have already witnessed this, and hopefully, he’ll share those one-to-ones!

55. Share a personal problem you’re currently experiencing with your partner, and ask them for their advice on dealing with it.

Open up about a problem at work or a problem in one of your friendships. Give him a short recap and ask for his advice on what to do. This will help you understand how he approaches problems and how rational he is.

56. What was your favorite movie when you were a child?

Most people love taking a trip down memory lane like this. And whether you know or like his favorite childhood movie or not, arrange to watch it together. Everyone loves a bit of nostalgia!

57. Tell me about one of your guilty pleasures.

couple laughing

Guilty pleasures: we’ve all got them whether we want to admit it or not. Maybe it’s a reality TV show, a band, or a cheesy song he LOVES, even though he knows it’s weird or as far away from cool as he could be.

FYI: his answer might make you laugh a LOT.

58. What was your first impression of me?

First impressions are a big deal, and we leave them with everyone we meet. So, what vibe did he get from you? How did you make him feel on that first date? Are you in tune with how you see yourself and how others see you?

59. If you could change one thing about the way you were raised, what would it be?

Even if we had a picture-perfect childhood, we can all agree that no parent has everything figured out. Maybe he wished things were a little less strict or a little more fun, or that his parents weren’t so protective of him as he grew up and gave him a little more independence.

60. Do you believe everything happens for a reason?

Younger people who are yet to experience significant trauma in their life are more likely to say yes to this. So if an older guy still believes this, it shows you he’s optimistic and looks for the good in all situations.

61. What’s one thing you want to do/see/achieve to make sure you die happy and fulfilled?

There might be one thing that stands out for him or a few things he still really wants to experience. Maybe you could make one of them happen for him as a surprise?

62. What do you find the most unattractive quality in a person?

I don’t like to dwell on negatives, but this question will help you see what his boundaries are regarding other people’s behavior or actions.

63. What’s one type of food or dish you’ve never tried but want to?

Because who doesn’t like talking about food?!

Maybe you can cook something together, or plan to head to a nearby restaurant, or even hop on a plane and experience the local, authentic version of the dish in question!

64. Do you believe there are other life forms in our universe apart from us?

One of the more fun questions to ask in a new relationship to see where his head is regarding aliens, other planets, energy, and spirituality.

65. What do you believe happens when a person dies?

The possibilities are endless. Reincarnation, heaven, a garden of paradise, another planet, nothing… Does he think there’s more out there? Maybe he already thinks he existed in a previous life? Who knows where this conversation will go.

66. Describe your fondest memory of all time to me.

This can be anything from his entire life. You’ll learn what his highlights have been so far and what brings him real joy and happiness.

67. If you could live anywhere other than where you live today, where would it be?

Has he ever thought about moving across the country, selling everything and buying an RV, or relocating to the other side of the world?

I think we’ve all thought about it at some point.

68. Tell me about a time when you failed at something.

Many of us feel shame and embarrassment when we fail at something, but failure is a beautiful thing—as long as we learn the lesson and grow from it.

69. What did you wish for most as a child?

boy playing

A pony in your back garden, ice cream for breakfast, a million dollars to spend however you liked, a brother or sister, a new pair of air jordans on your birthday, or, dare I say it—new parents?!

What stands out for him as something he wanted more than anything?

70. Is there something you never said to someone that you wished you could go back and say?

Although it’s hard to admit, many of us carry regrets over things we did and didn’t say or do in our past. Unfortunately, most of us don’t get a chance at a do-over. Or by the time we realize we want to make things right, our chance has gone.

71. How do you show your love to the people you care about most?

You may already have a good idea of how he shows his love from how he treats you but does this match what he tells you?

72. How do you most enjoy receiving love?

This is a valuable question to ask in a new relationship because it helps you make him feel loved and appreciated in ways that matter most to him.

73. Do you ever wish you could be famous?

If he says yes, ask him in what way? Does he secretly long for the world to know his name, or does he want something a little more selfless, like being able to help people with his star power?

74. What was the most valuable lesson you learned from your last relationship?

Someone who is not learning anything from their past relationships is a red flag. There is always something to be learned about ourselves—even if it’s difficult to accept at first.

75. If you were given a year off from your work or business, what would you do?

Does he long for adventure, globe-trotting, or a break from the status quo? Or does he love his work and could think of nothing worse than being away from it that long?

76. What’s one thing you will do differently from your childhood if you have your own kids someday?

This is a great question to explore the topic of kids—whether he wants any (or more) and how he wants to raise them. Are you on the same wavelength?

77. What does it feel like when you’re in love?

Love is a different experience for us all, and explaining your emotions this way can be challenging. Be patient as he tries to share his with you.

Conclusion: these questions are guaranteed to bring you closer together in your relationship

Remember to have fun with this list and take it in turn to ask and answer questions. Pick the ones that you most want to know about, and make sure you mix them up so that it doesn’t turn into a job interview for him!

Have you ever asked (or answered) any of these questions in a new relationship? And how did they help your connection?

Let me know in the comments below, ladies.

questions for a new relationship

PS. If you’re ready to start making men pursue you for love, then join me on this free webinar to discover the 3 steps to building emotional attraction – Register here to get started (it’s 100% free).

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Adam LoDolce

Love Strategist

My true passion in life is transforming your love life by giving you specific tools and techniques that you can use to attract long lasting love. I got started when...Read Adam's Story

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