48 questions

First date questions

The standard first date runs on a script: what do you do, where are you from, do you have siblings. It is a CV exchange, and it produces the strange outcome of two people learning each other’s biography while forming no impression of each other at all. You leave able to summarise them and unable to say whether you liked them.

What actually tells you something is how a person answers, not what they answer. Do they think before speaking. Do they ask you back. Do they say something slightly true rather than something safe. The questions below are chosen because they are hard to answer on autopilot, which is the whole trick.

They are also chosen to be answerable by a stranger. A first date is not the moment for anything that requires trust you have not built, and the section at the end covers what to leave alone entirely.

Openers that beat "what do you do"

Same social function, much better return. These let someone show you their personality rather than their job title.

1What did you do today before this?
2What have you been enjoying lately, anything at all?
3What is taking up most of your head space this week?
4How did you end up in this city?
5What would you be doing tonight if you were not here?
6What is something you are looking forward to?
7What did you want to be when you were a kid?
8What is the best thing you have eaten recently?
9What is something you have changed your mind about lately?
10What do you do that has nothing to do with work?

Questions that show you how they think

These are the useful ones. You are looking at reasoning and humour, not collecting the answers.

1What is an opinion you hold that most of your friends do not?
2What is something you are good at that took you a long time to learn?
3What do you find genuinely difficult that others seem to find easy?
4What is the most interesting thing you have read or watched this year?
5What would you do with a free year and no obligations?
6What is a small thing that reliably ruins your day?
7What are you unreasonably competitive about?
8What is a decision you are glad you made against advice?
9What did you believe at twenty that you find funny now?
10What is a compliment you would like to be given?

Light and funny

For when the conversation stalls, or when it has been earnest for too long and needs air.

1What is your most irrational fear?
2What is the worst haircut you have had?
3What is a hill you would genuinely die on?
4What is your most-used emoji, and does it represent you?
5What would the title of your autobiography be?
6What is something everyone loves that you cannot stand?
7What is the strangest job you have had?
8What is your useless talent?
9What is the last thing you searched for on your phone?
10What would you take to a desert island, other than the sensible options?

Questions for the second half of a good date

Only if it is going well. These ask for slightly more than a stranger owes you, so they need the date to have earned them.

1What are you actually looking for at the moment?
2What did your last relationship teach you?
3What do you need from people close to you?
4What is something people misread about you?
5When do you feel most like yourself?
6What are you working on about yourself?
7What does a good life look like to you, in ordinary terms?
8What would you want someone to know about you early?
9What is a friendship that has shaped you?
10What are you hoping this is?

What not to ask on a first date

These come up often and they all cost more than they return. Worth knowing which ones to steer around.

1Anything requiring a detailed account of an ex.
2Salary, or anything that reads as an estimate of it.
3Body count, weight, or anything about their body at all.
4Why they are still single, in any phrasing.
5Whether they want children, on a first meeting.
6Anything about a bereavement or trauma they have not raised themselves.
7A rapid series of questions with no answers of your own in between.
8Anything you have obviously already read about them online.

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

What is a good first question on a date?

Something about today rather than about their life. "What did you do before this?" is easy, specific and gives them somewhere to go, whereas "so, what do you do?" starts the CV exchange that most first dates never escape.

How do I avoid the date feeling like an interview?

Answer everything you ask, and go first on anything that requires the slightest exposure. Interviews are one-directional; conversations trade. If you notice you have asked three questions in a row without offering anything, tell them something instead of asking a fourth.

What should you not ask on a first date?

Exes in detail, money, bodies, and anything they would have to trust you to answer. The specific failure is asking for intimacy you have not earned yet, which most people experience as pressure even when it is meant warmly.

How do I know if the date is going well?

They ask you things back, unprompted, and the conversation moves away from the questions rather than depending on them. Sustained interest that has to be generated by whoever is asking is usually politeness rather than interest.

One question a day, answered together

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