Early on, the goal is not depth — it is finding out whether your ordinary days would fit together. That is mostly made of small things: how someone spends a Sunday, how they react when plans collapse, what they do when they are tired. The first two sections stay light on purpose. The third gets slightly more serious, and is best saved until the relationship has some months behind it.
Everyday habits
The most underrated section. Compatibility in a long relationship is mostly compatibility on ordinary Tuesdays.
- What is something about your daily routine that would surprise me?
- What is your go-to comfort food when you've had a long week?
- What is a personal pet peeve of yours that I should know about?
- How do you prefer to spend your Friday nights after a busy week?
- What is your favorite way to unwind on a Sunday afternoon?
- How do you usually react when plans change at the last minute?
- Do you consider yourself more of an early bird or a night owl?
- What does your ideal morning actually look like?
- What is a chore you genuinely do not mind doing?
- How much alone time do you need in a normal week?
- What is your phone-in-the-evening habit honestly like?
- What is something small that ruins your mood more than it should?
What they enjoy
Easy, warm, and useful — this is where you find the things you could start doing together.
- What kind of vacation do you enjoy most: relaxing on a beach or exploring a new city?
- What was your favorite subject or interest when you were in school?
- What is one habit or skill you are currently trying to learn?
- Who is the person in your life that makes you laugh the most?
- What is something small that instantly brightens your day?
- What is a movie or show you could rewatch anytime without getting tired of it?
- What is a restaurant or meal you've been wanting to try lately?
- What is your favorite season of the year and why?
- What kind of music do you listen to when you're driving alone?
- What is something you would happily do every weekend?
- What is a place near here you love that I probably have not been to?
- What is something you are unreasonably enthusiastic about?
Gently looking ahead
Save these for a few months in. They are not heavy, but they do assume you have both decided this is going somewhere.
- What is something you are looking forward to in the coming months?
- What is a compliment someone gave you that you never forgot?
- What is a goal you have for yourself by the end of this year?
- What has been your favorite memory of us so far?
- What is something you have enjoyed about getting to know me?
- What is important to you in how a relationship works day to day?
- How do you like to handle it when something bothers you?
- What is something you are hoping I will ask you about?
- What does a good weekend together look like to you?
- What is something you would want me to know before things get serious?
- What is a pace that feels right to you?
- What is something you want to do together in the next few months?
Questions about these questions
Are these too much for a first or second date?
The first two sections are not. Habits and enjoyment questions are what a good early date is made of. The third section assumes a few months of history and would land oddly on date two.
What if the answers reveal we are quite different?
That is the questions working. Difference in habits is normal and often fine — the useful thing is finding out early which differences you both find interesting and which ones you would find exhausting.
How do I keep it from feeling like a job interview?
Answer everything you ask, and let a good tangent kill the rest of the list. Three questions and an hour of digression beats twenty questions answered in order.
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