Dating is complicated, but getting to know each other better should be the goal. Ask these deep relationship questions to get closer.

Dating is fun and exciting. Did he mean to touch your leg? Did she just joke about staying over at your place or was she serious? These things are what makes dating so enjoyable, in the beginning, at least. As your relationship grows, it is important not to get too comfortable with assumptions you’ve made, but delve into deep relationship questions to make sure both of you know each other, and understand each other well.

Couples, no matter how long they’ve been together can and should always continue getting to know one another. This is how you grow a deeper bond and know that you’re with the right person. These deep relationship questions can help you connect on a more intense level, improve your intimacy, or even help you plan out your future together.

If you’re looking for more interesting questions that are specific to certain stages of the relationship, check out these links below before checking out the deep relationship questions below.

The best deep relationship questions to ask each other and know more

Whether you’re trying to feel out your new partner and see if you’re right for each other, or plan your soon-to-be marriage, these deep relationship questions will help you and your partner get the answers you seek.

#1 What is your relationship like with your parents?

#2 What was your first relationship like?

#3 What is the best way to handle a disagreement?

#4 What are your dealbreakers for the future?

#5 How do you handle stress?

#6 Do you have any regrets?

#7 What does this relationship mean to you?

#8 Where do you see us going?

#9 Do you believe in soulmates?

#10 What TV couple do you think we’re most like and why?

#11 If you could change one thing about me, what would it be?

#12 What have you always wanted to tell me but haven’t for whatever reason?

#13 What embarrasses you the most?

#14 What is your biggest fear?

#15 Do you struggle with self-confidence?

#16 How can I help when you’re upset?

#17 What does cheating entail?

#18 Do you have an advanced directive?

#19 Are you happy?

#20 How would you handle having a child with developmental issues?

#21 How do you feel about my family?

#22 Do you want children?

#23 Do you see marriage in our future?

#24 Where do you see us in 20 years?

#25 What is your perfect day like?

#26 When did you know you had real feelings for me?

#27 What rules do you live by?

#28 How important is your religion to you?

#29 What have you always wanted to ask me but never did?

#30 What about me worries you?

#31 What do you think I struggle with the most in life?

#32 What stresses me out?

#33 How do you view your childhood?

#34 Do you worry about our finances?

#35 What are your main priorities in life?

#36 When was the last time you broke out of your comfort zone?

#37 What do you think should be taught in schools but isn’t?

#38 Are you ashamed of anything?

#39 What’s on your bucket list?

#40 What is a trait you dislike?

#41 What are you most proud of yourself for?

#42 What are you proud of me for?

#43 Do you feel like you’ve missed out on anything?

#44 Where do you feel the most comfortable?

#45 Who in your life impacts you the most?

#46 Is there anyone in your life you’d like to cut out?

#47 What do you believe happens when you die?

#48 Do you believe in God?

#49 What is something you judge people for?

#50 What do you wish you could do but can’t?

#51 What is something you’ve always been curious about?

#52 If you could make one law, what would it be?

#53 If money was no object, what would your dream job be?

#54 Do you think you’re a trusting person?

#55 What do you want to change about yourself *not looks*?

#56 What is the healthiest part of your life?

#57 What was your biggest mistake in life?

#58 Do you think the world is progressing or regressing?

#59 What is the worst part about being lied to?

#60 Have you ever been cheated on?

#61 Have you ever tried recreational drugs?

#62 What is something you know will happen, but you are dreading it?

#63 What is the hardest thing you’ve gone through?

#64 Would you be open to couples’ therapy?

#65 If we had kids, who would you want their godparents to be?

#66 Do you think that you’re self-aware?

#67 Is it hard for you to forgive? Do you tend to hold grudges?

#68 What movie, book, or song hits closest to home for you?

#69 Have you ever had a near-death experience?

#70 How do you do your part for the environment?

#71 Do you think you follow or believe in stereotypes?

#72 How do you practice anti-racism?

#73 What celebrity do you look up to the most?

#74 What news story during your life impacted you the most?

#75 What is something expensive that’s worth the money?

#76 What are some societal standards that you question?

#77 What do you want to be remembered for?

#78 What is something you were surprised to learn recently?

#79 How do you feel about the justice system?

#80 Who do you trust?

#81 Who is someone most people like but you don’t?

#82 When was the last time you cried and why?

#83 Do you consider yourself to be open-minded?

#84 Do you think you would be a good parent?

#85 What is a sign that warns you not to trust someone?

#86 Have you ever been diagnosed with a mental illness? Or believe you suffer from one?

#87 How do you feel about homeopathic medicine?

#88 How do you feel about social media?

#89 How likely are you to trust what you read online?

#90 Do you believe the government or corporations listen to us through our devices?

#91 Do you believe in conspiracy theories?

#92 What have been the biggest events in your life so far?

#93 What is your biggest guilty pleasure?

#94 How do you feel about your body?

#95 What is something you’re in denial about?

#96 What event in your childhood has impacted you the most?

#97 Which of your parents are you most like?

#98 How have I impressed you?

#99 Why do you think we work so well together?

#100 What makes me sad?

#101 Do you think we depend on each other too much?

#102 How important is it to take pictures?

#103 Do you miss the way things were before we became obsessed with the internet?

#104 Do you think we communicate well enough?

#105 Are we adventurous enough?

#106 What is the hardest part of being in a relationship?

#107 What is the best part about being in a relationship?

#108 What can you not forgive?

#109 Do you think we are equal partners?

#110 Do you think we have a good sex life?

#111 Are you afraid of having kids?

#112 What scares you the most about being a parent?

#113 How important is sex in a relationship?

#114 Have you ever cheated on someone?

#115 How did your last relationship end?

#116 Who is a couple you look up to?

#117 Are you a feminist?

#118 Do you have a nemesis? Who?

#119 How do you wish people would describe you?

#120 Do you think others see you as you see yourself?

#121 Do you trust me?

#122 If you could give your younger self advice what would it be?

#123 Would you ever sign up for a reality TV show? Which one?

#124 How do you describe me to other people?

#125 What do you want us to accomplish together?

#126 How much weight do you put on special occasions?

#127 Have you been in love before me?

#128 Do you have doubts about us?

#129 Were you looking for a relationship when we met?

#130 If one or both of us couldn’t have children biologically, what would you want to do?

#131 What are your retirement goals?

#132 How would you feel about your parents or mine living with us in the future?

#132 How do you show love?

#133 When do you feel loved by me?

#134 What do you miss about your childhood?

#135 What are your goals for this year?

#136 Would you rather rewrite your past or know your future?

#137 Where is a place that isn’t around anymore, but you wish it was?

#138 How do you feel about cancel culture?

#139 What do we have in common?

#140 What is our biggest hurdle as a couple?

#141 How important are gifts to you?

#142 If you could fix any problem in the world what would it be?

#143 What is something you think about every day?

#144 Do you think I’ve changed since we met?

#145 How have you changed in the last year?

#146 Do you wish we were more romantic?

#147 Do we surprise each other enough?

#148 Is there something missing from our relationship?

#149 Who do you miss most that isn’t around anymore?

#150 What is something you are 100% sure of?

All of these questions bond you and your partner in a new way and on a new level. I wouldn’t recommend simply sitting down and asking these questions in a list. Rather, pick the ones you want the answers to and which you are also prepared to answer.

Be open and release all judgment. These questions are a path for you to get to know each other better and strengthen your connection, not an excuse to judge or mock one another.

Use these deep relationship questions as a guide and really dig deeper together. You’ll be glad you did. Start with a couple of them, and you’ll realize that they can reveal so much so soon!


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