Skip the Small Talk—50 Questions That’ll Transform Your Date Night

Over the years, I’ve found that a laid-back but romantic dinner at home—as opposed to a night out—is much more desirable. Sure, the novelty of a restaurant meal is something to be savored, but I love the comfort and intimacy of a date night chez moi. Where to begin? Set the mood by dimming the lights, putting a favorite record on, and prepping a mouthwatering meal to roast in the oven. After that? Prepare for presence. To make any night with your partner more meaningful, I’ve curated a list of 50 questions for intimacy that will help guide your conversation to a deeper place.

While the ambiance is key to an intimate evening at home, without enticing conversation, even the most beautiful setting can fall flat. So let go of the stress of the day and come to the table with intentional, intimate questions to ask your partner.

50 Intimate Questions to Ask Your Partner

Here’s an important PSA to keep in mind: dating your partner can be more than an overpriced dinner or bouquet. With the right mindset, intention, and questions, setting aside these special moments can deepen your love and bring a renewed perspective to your relationship.

Similar to the famed “36 Questions to Fall in Love”, these 50 questions for intimacy have been broken up into five sets, with each subsequent set of questions becoming more intimate. Start from the beginning and go (and grow!) from there. May the conversations these questions inspire bring you to exciting places with your loved one. Because however you decide to spend your Friday evening, connection should be at the heart of your time together.

Questions for Intimacy: Level 1

Would you like to be famous? What would you want to be famous for? What does the perfect day look like to you? How would you spend it? What song always makes you think of me? If we could travel anywhere right now, where would you choose and why? What movie do you think would reflect our relationship? If you didn’t have to work, what would you do with your life? How do you feel our careers affect our relationship? What thing/object/activity always brings you joy? Describe what love looks and feels like to you. What are three qualities about me that you were first attracted to?

Questions for Intimacy: Level 2

How do you feel is the best way to confront a problem? How do you like to show love? How do you like to be shown love? What country do you think is the most romantic? What do you remember from when we were falling in love? When have you felt the most proud of me? Out of the five senses, which is the most sensual to you? What is my sexiest feature? Is there anything you’re afraid to accomplish that I can help you with? What makes our relationship strong?

Questions for Intimacy: Level 3

What makes you feel the most loved? Share a time you felt embarrassed. If we met again for the first time, but with all the knowledge of our relationship up to now, what would you want to say to me? What would your younger self think of our relationship? What is the best way I can make you feel loved? What’s a question you’ve always wanted to ask me but never have? If you could relive one day together, which would it be? What’s your favorite memory of us? Is our relationship physical enough for you? What would make it better in your eyes? What is the best part of our relationship?

Questions for Intimacy: Level 4

If you could, what would you have changed about your childhood? What is one thing that you’re afraid to tell anyone else? Who was the last person you cried in front of? Why? How and where do you like to be touched? Do you have any fantasies you would like fulfilled? What is the closest you’ve ever felt to me? Is there anything we haven’t tried that you’d like to? What difference do we have that makes us complementary? Share a time when our differences helped us understand each other. What aspect of our relationship do you feel would be important to teach others?

Questions for Intimacy: Level 5

What is your biggest regret? How and when did you know we’d make it as a couple? What is a fear we’ve never talked about? What do you feel is your biggest weakness? How can I support you with that? What was something your younger self lacked that you know or can do now? What have you learned about relationships from your parents? Can you describe a moment when you felt truly alive? What do you feel is the most important component of a family? Where do you see yourself in five years? Do you think it’s true that love is more than just a feeling?