46 New Relationship Questions for the First Few Months
The first months of dating are full of guesses. Does this person like surprises? How much space do they need? What are they actually looking for? Asking kindly beats guessing, and it sets a tone of openness early.
Press Next to draw the first question.
These questions move from playful first impressions to the conversations that help you figure out if you want the same things. Nobody needs to answer everything at once. Let the relationship set the pace.
All 46 new relationship questions
16 light · 16 medium · 14 deep
- What did you tell your friends about me after our first date? Light
- Did you tell any friends about our first date, and what did you say? Light
- What is your ideal low-key date for the next few weeks? Light
- Are you a big texter or more of a save-it-for-in-person person? Light
- What is a movie you think I need to see soon? Light
- What is your favorite way to spend a weeknight evening? Light
- Which of my habits have you already noticed? Light
- What restaurant should we absolutely try together? Light
- Are you more of a plan-ahead dater or a spontaneous one? Light
- What made you say yes to a second date? Light
- What is something you hope we get to do together this season? Light
- What is your love language guess for me so far? Light
- What song would be on a playlist about the last few weeks? Light
- What is one thing on your calendar soon that you are excited about? Light
- What is the funniest moment we have had together so far? Light
- Morning dates or evening dates? Light
- What does a good relationship look like to you, day to day? Medium
- How much alone time do you need to feel recharged? Medium
- When you are upset, do you want to talk it through or have some space first? Medium
- How do you feel about meeting each other's friends, and when? Medium
- What did you learn from your last relationship that you want to bring into this one? Medium
- How do you like to be comforted after a bad day? Medium
- What is a deal-breaker you have figured out over the years? Medium
- How often do you like to see someone you are dating? Medium
- What is something that makes you feel cared for that might surprise me? Medium
- How do you feel about sharing our relationship online? Medium
- What are you most nervous about when starting something new? Medium
- What would make you feel more comfortable bringing something up with me? Medium
- How close are you with your family, and how involved are they in your relationships? Medium
- What does being exclusive mean to you? Medium
- What is one thing you want me to know about how you handle stress? Medium
- What does a perfect apology look like to you? Medium
- What are you looking for right now in a partner, honestly? Deep
- Where do you see yourself in a few years, and what matters most in that picture? Deep
- What has made it hard for you to trust someone in the past? Deep
- What do you want this relationship to feel like a year from now? Deep
- What is a pattern from past relationships that you are trying not to repeat? Deep
- What makes you feel most respected by someone you are dating? Deep
- How do you know when you are falling for someone? Deep
- What would you need from me if you were going through something really hard? Deep
- What are your thoughts on marriage or long-term commitment, without any pressure attached? Deep
- Is there anything about your life you worry might be hard for a partner to understand? Deep
- What part of yourself do you usually keep hidden early on? Deep
- How do you want us to handle it when one of us feels unsure? Deep
- What would make you feel like we were really building something together? Deep
- What do you hope I will learn about you over time? Deep
How to use these
- Keep the first few dates in the light section, and add medium questions as you get comfortable.
- Ask the deeper questions in a calm setting, not over text or right before one of you leaves.
- Answer every question yourself as well, so neither person feels examined.
- If an answer surprises you, get curious before you get concerned.
Related questions
- Getting to know you questions47 questionsThe basics, the backstory and the small details.
- Fun questions49 questionsEasy, playful prompts for any night in.
- This or that questions48 questionsRapid-fire pairs for quick, revealing answers.
- Love questions47 questionsRomantic questions about how you fell and why you stay.
Questions people ask
When is it too soon to ask serious questions?
There is no fixed timeline, but most people feel ready for questions about goals and past relationships after a few dates of easy conversation. If a question feels heavy for the moment, it probably is, so save it.
Is it okay to ask about past relationships?
Yes, when the focus is on what someone learned rather than the details. Ask what they want to do differently, not for a full history.
Should we talk about the future this early?
Broad questions about what each of you wants in life are useful early because they save heartbreak later. Keep them open and pressure-free.