100 Questions to Ask Your Love Interest

Picture this: a date night, a cozy setting, and a chance to peel back the layers of your love interest’s mind and soul. We’ve curated this fantastic collection of thought-provoking, deep, and playful questions that will spark conversations you never even knew were possible. Get ready to ignite the flames of curiosity, intimacy, and connection with this list.

Part I: Introduction Questions

If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
If you could wake up tomorrow having gained any one quality or ability, what would it be?
If you could send a letter to your past self as your present self, what age would you choose and what would you say?
Complete this sentence: “I wish I had someone with whom I could share … “
What are 5 positive characteristics you’ve noticed about me? (take turns)
What are 5 positive characteristics you love about yourself? (You CANNOT use any of the traits mentioned in the previous question.)
If you could choose a superpower, what would you choose?
Do you believe there’s one person you’re ‘meant’ to be with?

Part II: “As a Person” Questions

What is the most important goal you are pursuing at the moment?
In what environments/situations are you the most like yourself? In what environments/situations are you least like yourself?
How do you know when you’re doing the right thing with your life or on the right path?
What do you want to change about yourself?
What is the biggest misconception people have about you?
What is the quickest way to get under your skin?
What would constitute a “perfect” day for you?
What is your favorite thing to do in your spare time?
What is the hardest decision you’ve ever made?
What are some of the quirks that you have?
When did you last cry in front of another person? By yourself?
What’s one thing you’ve never told anyone?
What were you like as a child?
What were your childhood aspirations, and how have they changed?
What is your biggest insecurity?
What is your religion, if any? Are you more of a spiritual or religious person?
How do you like to be treated when you’re upset? Do you want to be held or left alone?
What should you do more of? What should you do less of?
Do you have any strange habits, tendencies, or things you obsess about?
Do you prioritize your needs or do you tend to put the needs of others before your own?
Are you the type of person that holds grudges or easily lets things go?
What is your biggest pet peeve?
What is your favorite time of year?
Where is your ideal place to live? On a farm in the country, in a nice house on the water, or in a luxury downtown condo?
What’s the most stress relieving thing you can get/do for less than $20?
What do you want to get out of life?

Part III: Mindset Questions

What experience in your life made you mature the most as a person?
What is your greatest fear and your biggest desire?
What’s the hardest truth you’ve come to grips with?
What’s something you believe that most people disagree with?
What is the process you go through in your mind before you make a decision?
Is it hard for you to make up your mind? Once your mind is made up, how easy or hard is it to change it?
If you were running for president, what are three key things you would include in your campaign?
Do you follow your heart or listen to your brain when making important decisions?
What are you afraid of and why?
Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it? Do you plan to do it in the future?
For what in your life do you feel most grateful?
What is the greatest accomplishment of your life?
What is your most treasured and most terrible memory?
If you had an unlimited amount of money and resources, what would you do with them and why?
Is there anything that often comes in between you and success?

Part IV: Experiences Questions

What is the biggest risk you’ve ever taken?
What is your proudest moment?
What amazing adventures have you been on?
What is your ideal vacation?
If we dropped everything and went on a road trip, where would you want us to go?
Have you ever been to therapy? Would you go back?
Have you ever been arrested? If not, if you ever were arrested, what would it most likely be for?

Part V: “Love & All That Jazz” Questions

What relationship cliché do you think is true?
Do you believe in love at first sight?
How do you know that you are in love with someone?
What is your greatest strength and weakness in a relationship?
What do you value the most and the least in a relationship?
What are the top 5 things you need in a relationship?
What would a perfect day look like in your ideal relationship?
What is the biggest sacrifice you’ve ever made for a relationship?
Do you like to be in charge or are you okay riding in the passenger’s seat in your relationships?
What relationship role do you want your partner to play in? What role will you play?
How do you prefer daily communication to take place (text, call or in-person) when in a relationship and how many times a day is ideal for you?
What is the best way to draw you closer to me in a relationship and what pushes you away?
What are your views on the role of social media in your relationships?
What are your dealbreakers in a relationship?
Would you move to a different city or state for your partner?
What are your views on sex within a relationship and how much do you need it?
What are your views on marriage and how do you think you’ll know when you have met the right one to marry?
Do you believe that unconditional love exists or is all love conditional?
What are your views on long-distance relationships?
What is your stance on maintaining communication with exes?
What is your stance on your partner having friends of the opposite sex?
What are the things your partner can do for you that makes you feel loved?
What is more important in a relationship: an emotional connection or a physical connection?
Out of your friends and family, whose relationship do you admire the most? Why?
Besides I love you, what are three important words you should be careful to say in a relationship?
What are the two biggest lessons you’ve learned from previous relationships?
Do you think a relationship can recover from cheating?
Have you ever been in an emotionally, verbally, or physically abusive relationship?
What is your love language? (If you don’t know, take the quiz here.)
What is your attachment style? (If you don’t know, take the quiz here.)
What is your communication style? (If you don’t know, take the quiz here.)
What is your communication technique? (If you don’t know, take the quiz here.)
What is your listening style? (If you don’t know, take the quiz here.)
What is your arguing style? (If you don’t know, take the quiz here.)

Part VI: Family Questions

Who in your family do you think understands you the most?
What are some of your favorite family traditions?
What was your “identity” in the family? You know, some kids are the overachiever, or the goody-two-shoes, or the wild one, or the peacemaker. What was yours?
How close and warm is your family? Do you feel your childhood was happier than most other people’s?
Describe your relationship with your mother in 3 words? Describe your relationship with your father in 3 words?
If you could change anything about the way you were raised, what would it be?
How important is it that your family approves of the person you are dating or are going to marry?
Do you have children? If no, do you want any and if so, how many? If you do have children, do you want more and if so, how many more?
What are your thoughts on disciplining children?
If you had kids or if you have kids, what is your biggest hope and biggest fear for them?

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