50 questions
Getting to know you questions for a new relationship
The early months of a relationship have a strange quality: you are gathering enormous amounts of information about someone while being motivated not to notice anything inconvenient. Most of what later gets described as a red flag was visible in month two and politely filed away.
So these questions do two jobs. Some are simply the good parts of getting to know someone, the things that make a person specific rather than a category. Others are compatibility questions, and they are here early on purpose, because they are much cheaper to ask before you are attached than after.
None of this needs to be solemn. The best version of this happens over months, one question at a time, and mostly by accident.
The interesting basics
Standard territory, asked in ways that produce an actual answer rather than a category.
- 1What was your family like at dinner time?
- 2What did your teenage bedroom look like?
- 3Who were you closest to growing up?
- 4What did you think you would be doing at this age?
- 5How did you end up doing what you do?
- 6What is the friendship you have had longest, and why has it lasted?
- 7What did you do with your last completely free weekend?
- 8What is something you have always been like?
- 9What was the best year of your life so far?
- 10What is something you were obsessed with as a kid?
How they operate
These predict daily life together better than anything about interests or taste.
- 1How do you handle stress, in practice rather than in theory?
- 2What do you do when you are angry with someone?
- 3How do you like to be looked after when you are ill?
- 4Are you a talk-it-out person or a go-quiet person?
- 5How long do you need to recover from a bad day?
- 6What does your ideal weekend rhythm look like?
- 7How much time alone do you need?
- 8What do you do when you are avoiding something?
- 9How do you make decisions, quickly or slowly?
- 10What is your relationship with your phone at night?
Compatibility questions worth asking early
The section people skip. These are far cheaper now than in year two, and nothing here is heavy if it is asked lightly.
- 1What are you looking for at the moment, honestly?
- 2How do you feel about children?
- 3Where do you see yourself living long term?
- 4How do you handle money, and what makes you anxious about it?
- 5How close are you to your family, and what will that look like for us?
- 6What are your non-negotiables in a relationship?
- 7How do you feel about marriage?
- 8What does faith or religion mean in your life, if anything?
- 9How much do you drink, and how do you feel about it?
- 10What ended your last relationship, from your side?
What they need from a partner
Asked directly, because guessing at this is how two people who like each other end up disappointing each other for years.
- 1What makes you feel loved, specifically?
- 2What makes you feel unloved, specifically?
- 3What do you need when you are upset?
- 4What kind of reassurance actually works on you?
- 5How do you want to be told when something is wrong?
- 6What did previous partners get wrong about you?
- 7What is something you need that feels awkward to ask for?
- 8What makes you feel secure in a relationship?
- 9What is your worst habit in relationships?
- 10What would make you feel like a priority?
Lighter questions for the in-between
Not everything has to be load-bearing. These are the ones that make the early months enjoyable rather than diligent.
- 1What is the best day you have had this year?
- 2What are you good at that never comes up?
- 3What is your comfort film, and why that one?
- 4What is a place you keep meaning to go?
- 5What do you do on a Sunday when nobody is watching?
- 6What is the last thing you got properly obsessed with?
- 7What is a small pleasure you take seriously?
- 8What would you spend a windfall on first?
- 9What is something you would like to be better at?
- 10What is on your list for this year that you actually intend to do?
Keep asking without having to remember
The hard part of this is not the questions, it is the habit. Most couples read a list like this, have one good conversation, and never open it again. HeartTap exists mainly to remove that failure: it sends one question at a time to both of you, and hides each answer until you have both written yours, so neither of you drifts toward agreeing with the other.
Frequently asked questions
When is it too early to ask about children or marriage?
Earlier than most people think. Asked lightly and out of curiosity in the first couple of months, these are ordinary questions. Asked in month eight they arrive with weight, because by then the answer has consequences and both people know it. The awkwardness scales with attachment, not with time.
How do I get to know someone without interrogating them?
Spread it over months and trade every question for something about yourself. Getting to know someone is a slow accumulation, not a data-collection exercise, and the most useful things you learn will come from watching how they handle an ordinary Tuesday rather than from anything they tell you.
What are the most important questions to ask early in a relationship?
The compatibility section, and specifically what they need to feel loved. Two people can share every value and still make each other miserable by offering the kind of care the other does not register. That mismatch is easy to fix once named and nearly impossible to fix while both people are guessing.
What if their answers worry me?
Believe them. The most common mistake in early relationships is hearing an inconvenient answer, deciding it will change, and building on it anyway. It is entirely reasonable to decide something is workable, but do that consciously rather than by quietly filing it away.
One question a day, answered together
HeartTap delivers a question at a time from a library of over 2000, and keeps both answers hidden until you have each written yours. Free on iPhone and Android.