First Date Questions and What to Talk About
Entry No. 198 ·
By The IF Team
The best first date questions are open, a little specific and easy to answer with a story: “What’s been the best part of your week?”, “What are you into at the moment that you could talk about for hours?”, “Where’s somewhere you’d go back to in a heartbeat?” What turns them into a conversation is what you do next. Ask about the answer, share your own, and let the talk move from light to a little deeper as you both relax. Leave the heavy subjects — detailed stories about exes, money, family rifts — for when you know each other better.
If you worry about running out of things to say, or about sounding like a job interview, you are far from alone, and the bar is lower than you think. In Hinge’s 2025 research with young daters, most said they asked enough questions on first dates, while far fewer felt their dates did: a gap the app called a question deficit. The same report found that 85% of daters were more likely to want a second date when they were asked thoughtful questions. Genuine curiosity is rarer, and more attractive, than a clever line.
Some questions, of course, cannot be asked yet: the one you would put to a person you like who is seeing someone, or the one you hold back because you are. IF is for those. It lets anyone say how they feel, honestly, whatever their relationship status and whoever they have in mind, putting a feeling that grew offline into words that wait until the moment is right.
How to ask without it feeling like an interview
- Follow up before you move on. “Why that one?” or “What was that like?” is worth five new questions. In Hinge’s research, a follow-up to something said earlier was the kind of question daters valued most.
- Answer your own questions. A conversation is a trade; if you ask about their favourite trip, offer yours.
- Ask about feelings and choices, not just facts. “What do you love about your job?” goes further than “What do you do?”
- Let silences breathe. A pause is not a failure; it is often where the more interesting answer is forming.
- Notice what lights them up, and go there. Their face will tell you which topics to stay on.
Easy first date questions to start with
- What have you been up to this week that was actually good?
- What do you do when you have a free Saturday with no plans?
- What are you obsessed with at the moment — a show, a hobby, a podcast, a recipe?
- Where did you grow up, and what do you miss about it?
- What is the best thing you have eaten recently?
- What is a small thing that always makes your day better?
- How do you know the person who introduced us, or what made you swipe on me?
- What is something you are looking forward to?
Questions that go a little deeper
Once you are both relaxed, a few questions with more weight tend to make the date memorable. People are often more ready for them than you would guess. In twelve experiments, psychologists found that strangers enjoyed deep conversations more than they expected and found them less awkward than they feared, partly because they underestimated how interested the other person would be.
- What is something you have changed your mind about in the last few years?
- Who has had the biggest influence on the way you see things?
- What would you do with a year off and enough money to live on?
- What is something people often get wrong about you?
- What are you proudest of that you never get to talk about?
- What does a really good week look like for you?
Playful questions for when it is going well
- What is your most controversial food opinion?
- What is the worst film you secretly love?
- If you had to teach a class on anything tomorrow, what would it be?
- What was your most embarrassing phase?
- What is the most spontaneous thing you have ever done?
Questions about what you both want
It is fine to touch on intentions on a first date, as long as it feels like curiosity rather than a checklist. A light “What are you hoping for from dating at the moment?” or “What made you want to meet up?” tells you a lot and invites an honest answer. You do not need to settle anything tonight. If knowing early matters to you, intentional dating has more on asking without making it heavy.
What to leave for later
- The full history of your last relationship. A sentence is fine; a saga is not. There is a better time for it, and talking about exes with a new partner explains when.
- Money, debts and salaries. Interesting eventually, awkward on a first evening.
- Detailed questions about past partners, their body or their sex life.
- Anything that sounds like a test: “What would you do if…?” scenarios designed to catch them out.
- Rapid-fire lists. Fifty questions read off a phone feel like a survey, however good the questions are.
What the answers tell you
Questions are not only for keeping the evening moving. The way someone answers tells you more than the answers themselves. Do they ask you anything back? Do they talk about friends, colleagues and exes with warmth or with contempt? Do they light up about something, anything at all? Can they laugh at themselves? None of it is a test to pass or fail, and one nervous evening proves little, but curiosity, kindness and a sense of humour tend to show up early when they are there.
Then ask yourself a couple of questions on the way home. Did you feel more like yourself as the evening went on, or less? Would you like to hear the end of the story they did not finish? Those answers usually tell you whether you want a second date more clearly than any spark or lack of one, and the signs a first date went well can help you read the rest.
If the conversation stalls
It happens on even the best dates. Go back to something they mentioned earlier (“You said you’d just come back from Lisbon — what was the best bit?”), comment on what is around you, or simply say, with a smile, “I’ve completely lost my train of thought.” Honesty about a lull usually dissolves it. How to keep a conversation going has more ways back in, and first date tips covers the rest of the evening.
Where IF fits: the question you cannot ask yet
Every question above assumes you can ask it across a table. The one many people most want to ask never gets a table at all: would you ever go out with me? Sometimes it cannot be asked yet, because the person is seeing someone, or you are, and asking anyway would put them on the spot.
That question can wait honestly on IF. There, anyone, partnered or not, can tell whoever has caught their eye how they feel, turning something that started in real life into words that wait for the right moment. Write the question as an IF, a message of 250 characters or fewer; it stays closed while either of you has a partner, with no conversation allowed on IF in the meantime. Ask it as a real question, because when it opens, it is one they get to answer: “Every time we talk I leave with three new questions for you. Here’s the one I’ve been saving: would you ever let me take you out?”
The answer is theirs to give, in their own time. A yes opens a chat. A no is something IF keeps to itself: you are not told, and the IF simply leaves your list.
Two singles can ask face to face, or by Like if the other person is on IF, and acceptance opens a chat. Before an IF opens, someone already on the app can learn only that it has arrived, not who wrote it or what it asks. If they have not joined, Search will take their Instagram handle, number or email, as long as they gave it to you, and only the email makes IF send anything: a single short invitation.
The first IF you send costs nothing. Put the question you have been saving into it, and let it be asked properly.
Questions people ask
What should you talk about on a first date?
Whatever lets both of you tell stories: what you love doing, places you have been, what you are excited about, how you spend your time. Start light, follow their enthusiasm, and let the conversation go deeper as it warms up.
What questions should you not ask on a first date?
Anything that feels like an interrogation or a judgement: how much they earn, why their last relationship really ended, how many people they have dated, or anything about their body. Questions with a hidden test in them tend to land badly too.
How many questions should you ask on a first date?
Fewer than you think, with more follow-ups. A handful of good questions, each explored properly, makes a better conversation than a long list. If you notice you have asked three in a row without sharing anything, offer a story of your own.
Is it okay to ask what someone is looking for on a first date?
Yes, asked lightly. Most people appreciate knowing whether you want something casual or serious, and a relaxed question invites an honest answer. Just do not treat their reply as a contract; plenty of people are still working it out.
Ask, listen, and ask again. And if the question that matters most has to wait for better timing, put it in an IF so it is ready the day it can be answered.