Questions to Ask Yourself Before Dating
Questions to ask yourself before dating, whether this is your first time or you are starting again after a break. The 52 here run in five groups: whether you are ready and why now, what the last relationship left behind, what you want and where your limits are, what you are like as a partner, and the practical side, from time and money to staying safe.
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The questions
Each question, and why to ask it
Readiness
Why do I want to date now, and what changed in the last month or two?
Why ask it
A specific trigger is worth naming: a birthday, a friend's wedding, an ex moving on, a quiet winter. None of these is a bad reason, but the one driving you says a lot about how patient you will be. Someone answering an ex's engagement is in more of a hurry than someone who simply has free evenings again.
Am I over my last relationship, or only tired of thinking about it?
Why ask it
Picture your ex happy with someone new and notice what your stomach does. A flicker is normal. If you would spend a first date comparing, or hoping word gets back to them, give it another month and ask again.
Am I happy enough on my own that a partner would add to my life, not rescue it?
Why ask it
Look at a Saturday with nothing planned. If it is mostly fine, you can afford to be choosy and to leave when something is wrong. If it is the part of the week you dread, you will be tempted to settle for whoever fills it.
Am I emotionally available, or do I only like the idea of dating?
Why ask it
Available means letting someone see an ordinary bad day, not only turning up on time. A fair test is what you say when a close friend asks how you really are. If you change the subject with people you trust, expect to do the same with a date, and decide on one true thing you are willing to say.
What am I looking for over the next six months: company, something casual, a relationship, or a partner to build with?
Why ask it
Six months is short enough to answer honestly, unlike questions about what you want from life. Any of the four is a fair answer. The trouble starts when you tell a date one of them while hoping for another.
Could I say what I am looking for out loud on a second date?
Why ask it
An answer that embarrasses you gets softened: 'something casual' becomes 'seeing where it goes', and two people spend months on different plans. Say the plain sentence aloud once at home. It is far easier to repeat across a table than to invent there.
How many evenings a week can I actually give to dating?
Why ask it
Count from your real week: work, family, training, shifts and the nights you need alone. One free evening every two weeks is still enough to date on, as long as you say so up front and do not leave someone reading your slow replies as a lack of interest.
What would I have to stop doing to make room for someone?
Why ask it
Something has to give: gym sessions, a hobby, time with friends, evenings with the children, sleep. Deciding in advance what you will trade stops you resenting the new person for a squeeze you chose.
Am I dating because I want to, or because someone expects me to?
Why ask it
The pressure usually has a face: a parent asking about grandchildren, a friend group where everyone has paired off, an ex you want to be seen to have moved past. Picture telling that person you have decided to stay single for a year. If the thought comes as a relief, the wanting is more theirs than yours.
What am I hoping a partner will fix for me?
Why ask it
Wanting life to be easier with someone in it is ordinary. The risk is a relationship taken on to fix one thing, whether that is loneliness, the rent, boredom or an unhappy home, because it gets judged on that one thing and resented when the problem stays. Ask what you could do about it this month on your own.
Is this a steady enough stretch of my life to let someone new into it?
Why ask it
A new job, a move, exams, a loss in the family or a rough patch with your health all take the attention that dating needs. You do not have to wait for perfect calm, but if you are barely keeping up, say so on the first date or start in a couple of months.
Do I think well enough of myself to turn down someone who treats me carelessly?
Why ask it
Low confidence tends to show up as gratitude for the bare minimum. Think of the last time someone was offhand with you and how long you put up with it. That length of time is the thing to shorten.
If nothing comes of this for a year, will I be all right?
Why ask it
A year of first dates that lead nowhere is a real possibility, so answer for that version. If it would be genuinely bad for you, build up the rest of your life alongside the dating: the friends, the work, the thing you do on Sundays. A date can usually tell when they are being asked to be all of it.
The past
Am I still in touch with an ex, and what is that contact for?
Why ask it
Contact is not automatically a problem: shared children, a lease or a friend group can all require it. It does change what you can offer someone new. If you would hide the messages from a person you had been seeing for a month, you already know what the contact is for.
Is there someone I would drop a new person for if they came back?
Why ask it
An uncomfortable question with a clear use: if someone is being kept in reserve, everyone you meet is auditioning against a person who is not in the room. Better to know that now than to explain it in six weeks.
What did my last relationship teach me that I would do differently this time?
Why ask it
Aim for something you did, not something they were. 'Pick someone kinder' is a wish. 'Say when I am annoyed instead of saving it up for a month' is a habit you can practice from the first week.
When someone last ended things with me, what reason did they give?
Why ask it
You do not have to accept their version, but it is an outside account of what you are like to be with, and those are hard to come by. If two different people gave the same reason, take it more seriously than anything you would write on a profile.
What have I not told anyone about how my last relationship went?
Why ask it
The unsaid part is often where your own behavior sits, or where something was worse than you have admitted. A date does not need to hear it, but you should be able to say it to yourself. If the unsaid part is that you were frightened or hurt, tell someone you trust before you start again.
Do I keep choosing the same kind of person, and how has that gone?
Why ask it
Line up the last three people you fell for and look for what they share: hard to reach, much older, in need of looking after, exciting and unreliable. A type only matters when the shared trait is also the reason each one ended.
Which warning signs have I explained away before?
Why ask it
Recall the actual excuse you made: they are stressed at work, they are different when it is only the two of us, it was a joke. You are more likely to catch yourself making the same excuse again than to spot the sign itself.
Am I carrying a hurt that a new person would end up paying for?
Why ask it
Being cheated on, lied to or left without a word tends to turn into checking, testing or keeping people at arm's length. Work out which ordinary behavior, a slow reply or a changed plan, is likely to set you off, so you can tell a memory from a real problem.
What did the couples I grew up around teach me to expect?
Why ask it
Whoever raised you showed you one version of love: steady, loud, silent, on and off. The familiar version pulls even when it was not a good one, so say which parts you want to keep and which you are finished with.
What I want
Which three qualities do I need in a partner, and which are only nice to have?
Why ask it
Three is a deliberate limit, because a list of twenty rules out everybody and guides nothing. Test each one by asking whether you would end an otherwise good relationship over its absence. If you would not, it goes on the nice-to-have side, next to height and taste in music.
Which of my values would I not bend for anyone?
Why ask it
A value you really hold is one you have already paid for: a friendship that cooled, a job you left, an argument you would not back down from. Start from those, whether they are about honesty, faith, money or drinking. On a date, listen for the same thing in their stories, since few people announce their values but most will tell you what they gave something up for.
Do I want marriage or children one day, and how soon do I need to know someone else's answer?
Why ask it
Undecided is allowed, and when you are young it is a perfectly good answer. If you are sure either way, saying so within the first few dates is a kindness, before two people get attached to different futures.
How much say do my faith, my culture and my family have in who I date?
Why ask it
For some people the answer is none, and for others it is the first filter. Be honest about which you are. Dating someone your family will never accept means a choice sooner or later, and the other person should hear that from you early.
What do I want my own life to look like in two or three years, with or without a partner?
Why ask it
Name what is already in motion: a course to finish, a city you mean to leave, a job with long hours, something you are saving for. Anyone new has to fit around those plans or change them. It is much easier to see which is happening when the plans were written down before you met.
What would a good relationship look like on a weeknight?
Why ask it
Grand gestures are easy to picture and tell you little. The weeknight version is what you would live in: who cooks, how much you talk, whether you are in the same room or happily apart. It also gives you something concrete to hold a real person up against.
How do I want to feel when I am around the person I am dating?
Why ask it
Write the words down now, before there is a face attached: relaxed, curious, a bit braver, free to be silly. Early attraction can feel a lot like nerves, and the list helps you tell being on edge from being interested.
How do I show I care, and what makes me feel cared for?
Why ask it
Some people cook, some fix things, some say it, some just turn up. A mismatch here is common and fixable, but only if you can tell a partner that a text at lunchtime means more to you than a present.
Where am I too picky, and where not picky enough?
Why ask it
It is easy to be strict about what a profile shows, such as age, looks and job, and lenient about what hurts later, such as lateness, sulking and vague plans. Try moving some of that strictness from the first list to the second.
What are my two real deal-breakers, and have I ever actually walked away over either?
Why ask it
Stated limits mean little without a record. If you have overlooked the same thing twice before, plan the specific action, not the principle: what you will say, and by when.
What are my boundaries for the first month of dating?
Why ask it
Set them before you meet someone you like, because once you do, everything starts to feel negotiable. Common ones are repeated late cancellations, messages that only ever arrive after midnight, being kept away from their friends, and pressure to get physical or exclusive before you are ready.
What pace am I comfortable with, and what will I say if someone wants to go faster?
Why ask it
Pace covers how often you see each other, how soon things get physical and when you meet each other's friends. Have a sentence ready, such as 'I like you and I want to slow this down.' The way a person reacts to hearing it tells you a great deal about them.
As a partner
What do I do when I start to like someone?
Why ask it
Most people have a pattern: texting constantly, going quiet to seem unbothered, rearranging their week, or losing interest as soon as it is returned. Naming yours lets you catch it in week two instead of explaining it in month three.
How do I behave when I am not sure where I stand?
Why ask it
This is where dating actually gets difficult, and the honest answer is often waiting, checking, or asking friends to interpret a message. If your instinct is to guess rather than ask, decide now what you will ask and when.
If I described myself honestly as a partner, what is the difficult part?
Why ask it
Everyone has one: long hours, a demanding family, a short temper in the mornings, a habit of withdrawing. Knowing your own hard edge lets you mention it early instead of hoping it stays hidden until someone is attached.
What do I actually bring to a relationship?
Why ask it
Answer with things a friend would confirm: you remember what people tell you, you stay calm in a crisis, you make dull errands fun. If the list leans on looks or income alone, put some time into your own life alongside the dating.
How do I argue with someone I care about?
Why ask it
Anyone who has shared a kitchen with you knows your style: going silent, keeping score, raising your voice, or giving in to end it and resenting it afterwards. Ask one of them if you are not sure. The first disagreement with someone new goes better when you can say 'I go quiet when I am upset, give me an hour.'
How do I take it when someone is not interested?
Why ask it
Dating involves a lot of polite no, often with no reason given. If one unanswered message can sink your week, keep fewer conversations going at once, and decide beforehand that a no is news about fit and not a verdict on you.
How will I tell someone I do not want to see them again?
Why ask it
Write the two-sentence message now: thank you for the evening, I did not feel a match. People who have it ready tend to send it, and people who do not tend to go quiet. The exception is anyone who has frightened you, who is owed no reply at all.
What do I need to be honest about in the first few weeks?
Why ask it
The usual list is children, a marriage that has not legally ended, religion, whether you want monogamy, a health condition, and whether you plan to move. Each is easier to say at week two than at month four. Later on it is the delay, more than the fact itself, that feels like a betrayal.
Which parts of myself do I hide when I want someone to like me?
Why ask it
The loud laugh, the faith, the odd hobby, the fact that you are in bed by ten. Whatever you hide has to stay hidden or come out later, and both are tiring. Letting it show on the second date also sorts people faster than any question you could ask them.
How much time to myself do I need, and do I ask for it or just disappear?
Why ask it
Some people recharge alone, and some feel shut out when a partner does. Saying 'I need one evening a week with nobody in it' sounds odd for ten seconds. It prevents the version where you go quiet and the other person assumes the worst.
Practical
Where am I going to meet people: apps, friends, or the places I already go?
Why ask it
Each route suits a different temperament. Apps bring volume and a lot of small talk with strangers, an introduction through friends comes with a reference, and a class or club lets someone get to know you over weeks. Pick the one you will keep up, not the one you think you ought to use.
How long will I spend on dating apps each day before it stops being good for me?
Why ask it
Set a number, such as twenty minutes after dinner, and check your mood when you close the app. If you mostly feel worse, the limit is too high or apps are the wrong route for you.
What can I afford to spend on dates, and how do I feel about who pays?
Why ask it
Drinks, tickets and travel add up over a month of first meetings, and a walk with a coffee tells you as much as dinner does. Settle your view on splitting the bill in advance, so it is a preference you state and not an awkward pause when the check arrives.
How will I keep myself safe when I meet someone new?
Why ask it
Decide the routine once so you are not arguing with yourself each time: a public place, your own way there and back, and one friend who knows the name and the time, or a parent or trusted adult if you are a teenager. Anyone who objects to that has told you something.
Who will I talk to about the people I meet, and do I want their running commentary?
Why ask it
A friend who mocks everyone you mention, or a parent who asks about marriage after two dates, changes how you behave. Choose one person to talk to and consider keeping the early weeks otherwise private.
Am I comfortable seeing more than one person at first, and what will I tell each of them?
Why ask it
Early on, plenty of people talk to several matches at once, and plenty find that impossible. Neither is wrong. What keeps it fair is never claiming to be exclusive when you are not, and answering truthfully if you are asked.
A few dates in, what will I be looking at to decide whether to continue?
Why ask it
Pick two or three observable things: whether they ask you questions, how they treat staff, whether plans happen when they say they will, how you feel on the walk home. Otherwise the decision gets made purely on nerves and attraction.
How will I know it is time to take a break from dating?
Why ask it
Signs worth watching: dreading dates you arranged yourself, telling the same three stories on autopilot, feeling bitter about people you have not met yet. A month off does no harm, and you are likely to come back curious again, which a first date needs more than anything.
Getting Ready to Date
Practical guidance for the conversation itself
Worth Doing First
Take one group at a time
A list this long is too much for one sitting. Take a group an evening, write the answers down, and mark the three you found hardest to answer. Those three are the ones to read again after your first few dates, when you have behavior to check them against.
If you have not dated before
Most of the group called The past is not yours to answer yet. Keep the question about the couples you grew up around, and answer the ones about patterns and warning signs from your friendships, which leave the same kind of evidence. If you are a teenager, add one step: tell a parent or another adult you trust that you are starting to date.
Say what you want, early and plainly
One sentence on the first or second date about what you are looking for can save months. A hint tends to get a hint back. A plain statement usually gets a plain answer, and if it gets a dodge, that is worth knowing too.
Check the practical mismatches before the emotional ones
Children, location, monogamy, religion and whether either of you wants marriage are not subtle questions of compatibility. They have yes or no answers. Asking in the first couple of weeks feels blunt, and it spares you both the ending where nobody did anything wrong.
Keep your own week running
Do not cancel the class, the friends or the training for someone you have met twice. It protects you if it ends, and it makes you better company while it lasts.
Notice how you feel afterwards, not just during
The walk home is more informative than the date. Relief, flatness or a need to reread the conversation to check you did well are all worth recording, because you will forget them by the next time they text.
Take basic precautions when meeting strangers
Meet somewhere public the first time, tell one person where you are going and when you expect to be back, arrange your own way home, and do not leave a drink unattended. A short video call beforehand is a reasonable check that the person matches their photographs.
Two Short Exercises
A readiness check, fifteen minutes on paper
- 1Write what you want from the next six months in one sentence.
- 2Write how many evenings a week you can give it, and which ones.
- 3Write the two things you would end it over, and what you will say if they happen.
- 4Write what you need to disclose in the first few weeks.
- 5Write one thing you did in your last relationship that you would rather not repeat.
- 6Write the two-sentence message you would send to end things kindly, so that it exists before you need it.
- 7Read it back and cross out anything you would not be willing to say out loud.
What to cover, and roughly when
- 1First couple of dates: what you are each looking for, in general terms.
- 2First few weeks: children, whether you are seeing other people, where you live and whether you plan to stay.
- 3Around the point it becomes regular: exclusivity, the pace you are each comfortable with, and how you each handle disagreements.
- 4Before it becomes serious: money, family expectations, religion, and health issues that would affect a partner.
- 5At every stage: whether the answers you are getting match the behavior you are seeing.
Common Traps
- Dating to prove something after a breakup. It is a common reason to start, and the cost usually lands on the person you date, not on your ex.
- Auditioning instead of noticing. Spending a date working out whether they like you leaves no attention for whether you like them.
- Talking about an ex at length. Some context is normal; a running account tells a new person exactly where your attention is.
- Treating a checklist as compatibility. Height, job and hobbies are easy to screen for and say little about how two people get on when a plan falls through or one of you is tired.
- Asking for commitment while quietly keeping options open. Whatever the intention, it is the behavior that gets remembered.
- Deciding after one date. First meetings favor the confident and the well-practiced, so unless something felt wrong or unsafe, a second is usually a fairer test.
- Waiting to feel completely ready. Nobody arrives fully prepared, and the useful question is whether you can be honest about where you are, not whether you have finished working on yourself.