Questions to Ask a Guy to Know His Intentions
Questions to ask a guy to know his intentions, whether you have been on two dates or have been seeing him for months without a name for it. They start with what to ask a guy before dating him in earnest, which is what he is looking for and whether he has room for it, then move through his past, the effort he puts in, whether he is a gentleman when there is nothing in it for him, and the future. The last group is for before getting serious: the conversation about being exclusive, and what each of you means by the word.
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The questions
Each question, and why to ask it
Early on
Are you looking for something serious, or seeing what happens?
Why ask it
Two answers are on offer and neither is the wrong one, which makes the true one easier to say. Seeing what happens is a fair way to date. It only becomes a problem when you want the other thing and stay anyway, so decide before you ask what you will do with each answer.
What are your intentions with me?
Why ask it
Said flat, it sounds like a father on the porch, so say it lightly, and after enough dates that he could have formed some. A man who knows what he wants can usually put it in one sentence. A speech about not believing in labels is also an answer, and you can take it as one.
What are you looking for in a partner?
Why ask it
Listen for whether he describes a person or a convenience. Kind, funny and wants a family one day is someone he has pictured sharing a life with. 'Someone easygoing who does not need much' is mostly a description of what he is prepared to give.
Is this a good time in your life to be dating someone?
Why ask it
Wanting a relationship and having room for one are different things. A man in the middle of a move, a new job or a breakup can like you a great deal and have very little to give this year. Bad timing can mean bad for anything or only bad for something serious, and it is worth knowing which.
Do you date one person at a time, or several until it gets serious?
Why ask it
Easy to answer on a second or third date, because it is about his habit and not yet about you. Neither answer is wrong this early. What you learn is what he will assume is allowed until one of you says otherwise.
What are you not looking for right now?
Why ask it
People who go vague about what they want can often say at once what they do not. Nothing serious, nothing long distance, nothing that takes up his weekends: whatever he rules out, check whether you are standing in it.
What do you think about casual dating?
Why ask it
Asking for his opinion in general is easier on both of you than asking about his plans for you. If he says casual suits him at the moment, give that sentence more weight than any warmer one that follows it. If he says he is tired of it, ask what he is doing differently this time.
What do you like about being single?
Why ask it
Whatever he lists is what a relationship would cost him: free weekends, nobody to answer to, the trip booked on a whim. A short list he would trade without much thought is very different from a long one he lights up over. It also gets a fuller reply than asking whether he likes being single, which invites a shrug.
What are your biggest priorities right now?
Why ask it
Work, an exam, a parent who is unwell, getting fit: note what makes the list. A relationship being left off is not a verdict, since few people think to name it unprompted. Ask where dating fits among the others and you will hear how much room there is.
What are your dealbreakers in a relationship?
Why ask it
Smoking, not wanting children, living in different cities: the practical ones tell you quickly whether you are ruled out. Vaguer ones such as 'drama' or 'someone needy' deserve a follow-up, because you want to know whether asking where you stand would count as either.
Do you see me as a friend, or as something more?
Why ask it
For when you spend a lot of time together and nothing has been said or done to make it a date. If the answer is friend you are in for an awkward week, which is still cheaper than a year of wondering. If he says he has never thought about it, let him, and raise it once more in a week or two.
What made you want to see me again?
Why ask it
A specific answer, something you said or the way you argued about a film, means he noticed a person. 'I had a good time' is thinner, though plenty of people go blank when asked this across a table. It counts for more if the answer is still that thin a month later.
What were you hoping to find when you joined the app?
Why ask it
Only for someone you met online. He made this decision before he knew you existed, so it is harder to tailor to you: a relationship, some company, something to do in the evenings. If you met another way, ask what made him start dating again.
What do you like about me that has nothing to do with how I look?
Why ask it
Fair to ask once you have spent a few evenings together. Listen for something you told him coming back: your job, your sister, the thing you are saving up for. A pause followed by a compliment about your smile means he has not got that far yet.
If you planned our next date, what would we do?
Why ask it
A day, a place and a reason he picked it show effort he is willing to spend on you. If every suggestion is a late evening at his place, say you would like to do something out first and see whether a second idea arrives.
Would you still want to keep seeing me if we took things slowly?
Why ask it
Yes is the easy thing to say, so the real reply comes over the next two weeks. Someone who meant it keeps making plans and lets the subject rest. Someone who did not gets busy, or raises it again each time you meet.
His past
How long ago did your last serious relationship end?
Why ask it
The gap matters as much as the story. Someone three months out of a long relationship may mean every word he says to you and still not be ready to act on it. Several years with nothing serious since raises a different question, which is whether he has wanted anything.
Why did your last relationship end?
Why ask it
Notice who does things in his version. 'We wanted different things' and 'I was not ready for what she wanted' are both fair, and the second tells you what he may not be ready for now. An account in which she was simply 'crazy', with nothing he would do differently, shows you how he may one day describe you.
What kept your longest relationship going?
Why ask it
Someone who can say what held it together, whether habit, effort or simply liking her, has thought about what staying takes. If his longest lasted a few months, ask whether the endings were his choice.
Have you ever been in love?
Why ask it
Yes or no matters less than how he talks about it. Someone who has been can usually say what it was like and what he would want again. If he says never, ask whether he came close and what got in the way, because whatever it was may still be around.
Has anyone you dated ever said she did not know where she stood with you?
Why ask it
It is a complaint people tend to remember hearing. One ex who felt that way is a mismatch. Several, all described as wanting too much too soon, is a pattern he has not looked at.
If your ex asked to try again, what would you say?
Why ask it
Staying in touch with an ex can be ordinary when there are children, friends or a lease to sort out, so contact alone tells you little. This asks whether it is finished for him. A flat no with a reason is what you hope for, and 'it is complicated' suggests part of him is still there.
What has made you end things with someone before?
Why ask it
What he has walked away over is a better guide than what he says he cannot stand. If his reasons were about pace, that she wanted more time, more plans or a label, notice that those are the things you are about to ask him for.
How do you tell someone you are no longer interested?
Why ask it
The answer is a preview of how this would end, if it does. A phone call or an honest message means you would be told. 'I am bad at that' or 'it usually fizzles out' suggests you would be left to work it out from slower replies.
Have you been with someone a long time without it turning into a relationship?
Why ask it
If he has, ask what kept it from becoming one and which of them wanted more. You are not after a verdict on him, only whether the reason he gave her is the reason you are hearing now.
Have you ever told someone you wanted something serious and then changed your mind?
Why ask it
Plenty of people who have dated for a while have, and admitting it counts for him, not against. The useful part is what changed and how he let her know: a conversation, or a slow fade she had to interpret.
Have you ever cheated, or been cheated on?
Why ask it
Ask it once there is some trust between you, and be ready to answer it yourself. A yes to the first half does not close the subject: whether he told her or was found out, and what he says about it now, is the part worth hearing. Having been cheated on can explain caution that would otherwise read as lack of interest.
Effort
How do you feel about me meeting your friends?
Why ask it
The easy reply is that he would love that, so listen for a name and a rough date. 'Come for drinks with them on Friday' is a yes. Months of 'definitely, sometime' is a no that has not been said out loud.
Has anyone in your life heard my name?
Why ask it
Meeting people takes arranging, but mentioning you costs nothing, so this is the lower bar. A brother, a roommate or someone at work knowing you exist means you are part of how he describes his life. Nobody knowing after a couple of months is worth raising before the question of meeting them.
Would you want me to meet your family?
Why ask it
Some families meet everyone and some meet only a fiancée, so find out what an introduction means in his before reading anything into the wait. Parents who live a flight away, or who are hard work, are real reasons. If his family is nearby, close to him and still off the table after many months, ask him plainly why.
Would you mind if I posted a photo of the two of us?
Why ask it
Check his habits before you read anything into the answer: someone who posts nothing at all is private, not hiding you. The case worth a conversation is the man who shares most of his life online and would like you kept out of it.
Can we plan something for a couple of weeks from now?
Why ask it
More a request than a question, and what you get back is a fact: either a day goes in his calendar or it does not. Pick something small, a show or a day trip, so that a no cannot be about cost. Hesitation over fourteen days is worth asking about directly.
I have noticed we mostly meet late and at short notice. Is there a reason?
Why ask it
You are describing what happens, not guessing why, which leaves room for a real reason: shift work, a child at home, an early start. A real reason usually comes with an offer to do it differently when he can. No reason and no change over the next few weeks suggests you are being fitted in around other things.
When you go quiet for a few days, what is happening?
Why ask it
Ask it when things are fine, not on day three of a silence. Some people go under when work or family gets heavy, can tell you so, and can manage a one-line message once they know it matters to you. If the reply is that you are asking for too much, he has told you how much contact to expect.
What does your week look like when we are not seeing each other?
Why ask it
You are listening for free evenings. Work, the gym, a league game on Thursdays and family on Sundays is a full life with one night left in it, and that night may be all he has to offer however much he likes you. Ask which part he would move, if any.
Which of us do you think usually suggests getting together?
Why ask it
Only worth asking if it is usually you. It lets him see the imbalance without being accused of it, and what he does in the two weeks after matters more than what he says. If you would prefer not to ask, leave the next plan to him and see whether one arrives.
If I needed a ride to the airport or help moving a sofa, would you want me to ask you?
Why ask it
Airport runs and furniture are where someone shows whether he sees himself in your life or only in your evenings. Being glad to be asked is the good sign, even when he cannot always do it. A joke about calling a taxi, made twice, has stopped being a joke.
A gentleman
What does being a gentleman mean to you?
Why ask it
Some men hear the word and think of holding doors and picking up the bill. Others think of keeping their word and never making anyone feel small, which is the version that lasts. If he calls the idea old-fashioned, ask what he would put in its place.
What is the rudest thing you have seen someone do to a waiter or a cashier?
Why ask it
He will tell the story gladly, and what he counts as rude is the information. Then watch him with whoever brings your food. Charm for you and curtness for the staff is manners used as a tactic.
When you are running late or have to cancel, what do you do?
Why ask it
The courteous version is a message before the time he was due, with another day offered in the same breath. Everyone cancels now and then. Going silent and turning up two days later with a joke shows how much your evening weighed with him.
What is a promise you kept when it would have been easier not to?
Why ask it
Keeping his word is most of what the old word gentleman meant. A small example counts: helping a cousin move on the hottest day of the year, going to the party he said yes to weeks earlier. Afterwards, see whether the small things he tells you, a call tonight or a plan for Saturday, happen.
How do you like to split the bill on a date?
Why ask it
There is no correct custom here: paying, splitting and taking turns can each be good manners, depending on where and how you both grew up. What matters is that he raises it kindly and does not keep score out loud later. Tell him what you prefer, since he cannot be considerate about something he has to guess.
How do you take it when someone you are dating says no to something?
Why ask it
No to another drink, to going back to his place, to a weekend away this soon: the size of it does not matter. You are hoping for 'then we will do something else' with no sulk attached. The last no you gave him is better evidence than anything he says here.
Do you tell your friends the private details about someone you are dating?
Why ask it
What goes into his group chat about her will one day be about you. A man with good manners can say he is seeing someone, and that it is going well, without passing round her messages or her secrets. If he laughs and says the boys hear everything, believe him.
What would you do if a friend of yours spoke badly about the woman he was seeing?
Why ask it
Manners shown to your face are the easy kind, and this asks about a room you are not in. 'I would tell him to cut it out' and 'I stay out of it' are both honest replies. They tell you different things about what he lets pass.
When did you last apologise to someone, and what was it for?
Why ask it
A recent, specific one, such as snapping at his brother on Sunday, means he can see his own behaviour and say so. 'I am sorry you took it that way' is not an apology, and a man who offers it as his example has told you how his sound. Struggling to remember any at all is the thing to notice.
If you worked out that you did not want what I want, how soon would you tell me?
Why ask it
Nobody can promise to want what you want, but he can promise not to keep you waiting once he knows. 'Straight away' should mean an awkward conversation in week six, not a slow fade through month six. If he says he would hate to hurt you, he has answered a different question.
The future
Where do you see this going?
Why ask it
The question everyone means, and the one most likely to get 'I am enjoying it, are you?' because it is so open. That reply is not a dodge on its own. It becomes one if he gives it again after you have said where you would like this to go.
What would you want this to look like in six months?
Why ask it
Six months is close enough to picture: how often you see each other, whether you have met his family, whether there is a word for it. If you have been together a while and he cannot name one thing he would want to be different by then, he may be happy with things exactly as they are, which is worth hearing him say.
Is there something later this year you would want us to do together?
Why ask it
Smaller than a five-year plan and easier to answer honestly: a trip, a concert, a wedding he has been invited to. Remember what he names. If it is never mentioned again, bring it up once yourself, and if it still goes nowhere it was only a pleasant thing to say.
What does your ideal relationship look like?
Why ask it
Ask for the ordinary week, not the highlights: how often the two people see each other, who makes the plans, how much time alone he would keep. Then set it beside what the two of you have. If his ideal has shared weekends and you meet once a fortnight, ask what keeps this from being that.
When you picture your life in five years, is there a partner in it?
Why ask it
You are asking about his future before asking whether you are in it, which is lighter for both of you. Some people describe a job, a city and a dog and never mention another person. Take that picture seriously, and check whether a partner was left out or simply taken for granted.
What does commitment mean to you?
Why ask it
The word covers everything from not dating other people to sharing a mortgage, and you want to know which he hears. Ask for an example from his own life: a relationship, a friendship, a job he stayed in when leaving was easier. If every example is a story about feeling trapped, that is his honest view of it.
Do you want to be married, or living with someone, at some point?
Why ask it
This is his view of commitment in general, kept apart from his view of you. A firm no is not a rejection of you, but it does set the limit of what this can become with him. 'With the right person' is an easy reply and means little until he can say what that person is like.
Do you want children?
Why ask it
It belongs on this list because it decides whether serious is even possible between you, and it is kinder to learn that at month three than at year three. 'Someday, maybe' is a fair answer early on. If it matters to you, say which way you lean so that he is not answering blind.
Are you planning to stay around here, or could you see yourself moving?
Why ask it
A transfer, a visa running out or a plan to move back home changes what this can be, and it is the kind of thing people leave out until they are asked. If a move is coming, the follow-up is whether he has pictured you in it or assumed this ends when he goes.
Is there anything you want to have done before you settle down with someone?
Why ask it
Finishing a degree, paying something off, a year abroad: a real condition comes with a rough end date, and you can decide whether to wait for it. A list that gets longer each time you ask is not a timetable, and you are allowed to say so.
Defining it
How do you feel about me?
Why ask it
Short, hard to ask, and the reply may well be 'I like you, obviously'. That is a start, so ask what liking you makes him want to do about it. Feelings and intentions are separate: he can be fond of you and still not want a relationship, and the second part is what you came to find out.
How would you describe us to someone who asked?
Why ask it
A concrete way into the conversation about what you are. The word he reaches for, seeing each other, dating, my girlfriend, tells you where he thinks you stand today. If he turns it around and asks what you would say, tell him, then ask again.
Are you seeing anyone else at the moment?
Why ask it
One word answers it, so anything longer is worth noticing. Before you have agreed to be exclusive, yes is not a betrayal, only something you needed to know. If he wants to know why you are asking, the reason is simple: it changes what you do next.
Are you still on the dating apps?
Why ask it
Narrower than asking about other people, and he can show you. A profile that is still up proves little in the first few weeks, but he should be able to say whether he is using it. Ask only if you are ready to answer the same question.
Would it bother you if I were seeing other people?
Why ask it
Ask it out of curiosity, never as a bluff. A relaxed no usually means he thinks of this as casual, whatever else has been said. If it would bother him, the next question is whether he wants to be exclusive.
Do you want to be exclusive?
Why ask it
Hints and jokes about labels do not count as asking, and this does. Yes, no and 'not yet, ask me in a month' are all replies you can work with. A change of subject is not, and it is fair to say that you still need one of the three.
When you say exclusive, what does that rule out?
Why ask it
Two people can agree to the word and mean different things by it: not dating others, not messaging them, deleting the apps. Settling the definition now is dull, and it prevents the argument in which both of you feel you kept your word.
How long do you usually date someone before you decide whether to make it official?
Why ask it
His usual timetable is something you can set against how long the two of you have been going. Well past it with nothing said is worth pointing out, along with the question of what is different this time. If he claims to have no usual, ask how it happened with his last girlfriend.
Is there anything making you hold back?
Why ask it
It assumes there may be a reason and invites him to name it: a divorce that is not final, a job move, a child, someone he is not over. A named obstacle can be weighed and given a time limit. 'Nothing, I just do not want to rush', said for the third time, is not an obstacle.
What do you think I am looking for here?
Why ask it
This finds out whether what you have said has landed. If he gets it right, you can go straight to whether he wants the same. If he is far off after months, correct him plainly and watch whether anything changes once he can no longer say he did not know.
How do you know when someone is worth being serious about?
Why ask it
His reply gives you a list to hold up against how he treats you: 'when I want her to meet my family' is easy to compare with whether you have. If he says he just knows, ask whether he knows yet.
I want something that is going somewhere. Is that what you want too?
Why ask it
It states your position before asking for his, so he cannot reply with whatever he guesses you are hoping to hear. Say it only when you mean it and know what you will do if the answer is no. 'I do not know' is honest, and worth one follow-up: what would help him know, and by when.
Asking where this is going
Practical guidance for the conversation itself
How to raise it
Start with the group that fits how long it has been
Early on is for the first few dates, when asking to be exclusive would be premature and asking what he is looking for is not. His past and Effort suit the weeks after that, once there is some behaviour to ask about. A gentleman fits anywhere, because it is about how he treats people in general and not yet about the two of you. Keep The future and Defining it for the point where you would act on the answer.
Say what you want first
A question about his intentions with no statement of yours leaves him guessing at the right answer. Say where you stand, briefly and without an ultimatum, and it becomes easier for him to say where he does.
Choose a calm moment, not a charged one
Not late at night, not by text, not while one of you is halfway out of the door. A walk at the weekend or an ordinary evening in keeps it a conversation and not a confrontation.
Ask one question and let it land
Each of these works alone. Ask three at once and it starts to sound like a case being made, and he will answer whichever is easiest.
Accept a real answer, including a disappointing one
If the reply is that he does not want anything serious, that is the information you asked for. Arguing him out of it, or agreeing to less than you want and hoping he changes, tends to bring you back to the same conversation later with more time spent.
Reading what you get back
Honest uncertainty sounds specific
'I do not know yet, give me another month' or 'I am still getting over something' is a workable answer, because it comes with a reason or a date you can return to. Warmth with no timeframe gives you nothing to return to.
Compare words with the calendar
Introductions, plans made further ahead than the weekend and time together in daylight are what interest tends to look like in practice. Where what he says and what the calendar shows keep disagreeing, give more weight to the calendar.
Note whether he asks you anything back
Someone weighing up a future with you usually has questions of his own. Replies with no curiosity in return can mean he is getting through the conversation, not having it.
To find out if he is a gentleman, ask about other people
Courtesy toward you on a date is the easy part, since he is hoping to see you again. The questions under A gentleman ask a man about waiters, friends, his word and hearing no, because how he treats people he has no reason to impress is harder to put on for an evening.
Watch for the deflection to your feelings
'Why are you so insecure' and 'you are overthinking this' move the subject from his intentions to your character. Neither answers what you asked, and it is fair to say so and ask again.
Common mistakes
Asking for a promise on the second date
Nobody can honestly tell you after two evenings where this will be in a year. Early questions are about what he is looking for and whether he has room for it. Pushing for more than that gets either a retreat or a promise he is in no position to make.
Hinting and hoping he picks it up
Jokes about labels and comments about other couples are easy to miss, on purpose or otherwise. The plain question feels riskier and costs less than months of not knowing.
Asking during an argument
Raised in a fight, it sounds like a threat, and the defensive answer you get is one neither of you would stand by the next day.
Taking the reassurance and stopping there
'Of course you are important to me' is kind and says nothing about intentions. It is fine to reply that you are glad, and that what you asked was whether he wants to be exclusive.
Asking repeatedly
If you have asked clearly and the answer is still unclear a few weeks later, the lack of one is what you have to decide on. Asking a fourth time is unlikely to produce what the first three did not.