Questions to Ask Guys About Girls
Questions for asking guys what they notice, how they approach someone and what they get wrong, whether that is a group on a long drive or one guy you want to understand better: a boyfriend, a brother, a friend. They run in five groups, from crush stories and making a move to where his ideas about women came from and which ones he has changed.
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The questions
Each question, and why to ask it
Icebreakers
What is the first thing you notice about someone, honestly?
Why ask it
Everyone has an answer ready for this one, which is why it works as an opener. In a group, watch how quickly the others call out anyone who gives the noble answer. One on one, ask how honest that first answer was and let him go again.
Who was your first crush, and what happened?
Why ask it
First crush stories are almost always funny and almost never flattering, so this loosens up the room. It also gets people telling stories rather than giving opinions.
What is the most embarrassing thing you have done in front of someone you liked?
Why ask it
The self-inflicted disaster is a safer story than an embarrassing thing done to him, and it gets better answers. Whoever volunteers first sets how honest the rest of the group is willing to be.
What is the worst thing you have ever said to someone you were trying to impress?
Why ask it
Something said is a different kind of disaster from something done, and most guys can still quote theirs word for word. Groups tend to escalate here, which is the point.
What is something you did because you thought it was attractive and later realized was not?
Why ask it
Asking about a retired behaviour is easier than asking about a current one, so people answer honestly. The answers usually involve teasing, playing it cool, or a phase of clothing.
What is the most useless piece of dating advice you have been given?
Why ask it
This lets him criticize the whole genre of advice, which is easier than criticizing himself. The advice he names usually came from someone he stopped trusting.
Making a move
What is your actual move when you want to talk to someone new?
Why ask it
Ask for the specific opening line or approach, not the philosophy. The gap between what men claim they do and what they describe doing is usually the funniest part of the evening.
What is the hardest part of approaching a woman you do not know?
Why ask it
Most answers come down to a fear of being embarrassed in front of other people, more than a fear of her. That explains a lot of behaviour that looks like arrogance or indifference from the outside, so ask what he does to get past it.
Do you prefer being asked out or doing the asking, and why?
Why ask it
Most men have a genuine preference here and have never been asked to justify it. The reason is more revealing than the answer, usually about fear of rejection or of misreading things.
How do you tell whether a woman is interested in you, and how often have you been wrong?
Why ask it
The second half is the useful part. A guy who says he has never misread a signal has either never risked anything or is not being straight with you, so ask for the time he got it most wrong.
Have you ever completely missed someone showing interest in you?
Why ask it
Almost every man has one of these and remembers it with real regret. It is also a soft way into a genuine conversation about how much signalling gets lost.
How long do you wait to text back, and is that on purpose?
Why ask it
Everyone has a theory about texting timing and few will admit to strategy. This is the question that starts the loudest argument in the group.
Has a rejection ever changed the way you approach women?
Why ask it
Listen for whether he learned something from it or hardened around it. The way he tells the story of one no is a fair preview of how he takes the next one. If it still sounds raw, do not push for details.
How do you handle it when a friend likes the same person you do?
Why ask it
This shifts the conversation from dating to loyalty and reveals how he ranks the two. Watch whether he has a rule or just handles it case by case.
Attraction
How do you know when you are into someone rather than just flattered by the attention?
Why ask it
This is a real distinction most people have never put into words. Answers reveal whether he has ever dated someone mainly because they were interested in him.
What is something you find attractive that you cannot really explain?
Why ask it
This gets past the standard list of traits into the genuinely idiosyncratic. Answers here are the ones people actually remember from the conversation.
What do you find attractive in a woman that you would not say in front of your friends?
Why ask it
Keep this for a conversation with one guy, since asking it in front of his friends defeats it. What he has been hiding is usually the gentler preference, like wanting to be looked after or liking someone louder than he is.
What kind of woman were you raised to want, and does she match who you actually fall for?
Why ask it
The gap between the two is where family expectation, culture and what he really wants run into each other. If he says there is no gap, ask who in his family would be most surprised by the last person he liked.
What does someone do that makes you relax around them?
Why ask it
Comfort is a different question from attraction and men are rarely asked it. The answers tend to be small and specific: being asked a question, not being tested, being allowed to be quiet.
What is a compliment from a woman that you still remember?
Why ask it
The one he can quote years later is rarely about the thing he is obviously good at. It is usually about something he was quietly unsure of. If he cannot recall one, do not fill the silence for him.
What is a compliment you have never received but would like to?
Why ask it
The answer is almost always about something he worked at rather than something he was born with. Nobody names their appearance, which itself is worth noticing.
What is the nicest thing someone has done for you that they probably do not remember?
Why ask it
This produces some of the most unexpectedly sincere answers on the page, usually about a small kindness at a bad moment. It changes the tone of the group in a good way.
Views on women
What is something you have seen women do well that you wish came more naturally to you?
Why ask it
This gets him observing rather than defending, which makes it the right first question when the talk turns to women in general. What he names shows the qualities he admires in practice, not the ones he thinks he should list.
Who was the first woman you looked up to, and what did she teach you?
Why ask it
Most men reach for a mother, grandmother, teacher or older sister. The lesson he names is often one he still measures people against without noticing, so ask where he sees it in his life now.
Who in your life gave you your idea of how to treat someone?
Why ask it
This asks for a person rather than a principle, which is why it goes further than most of the list. Whether he points to a parent, a friend or the absence of anyone tells you where his habits started.
Where did most of what you learned about women actually come from: family, friends, movies, or the internet?
Why ask it
Naming the source separates what he was told from what he has lived. A guy who traces his views back to a locker room or a screen often hears how thin that is as he says it, and you do not need to point it out.
What did the men around you growing up say about women when no women were in the room?
Why ask it
This asks for the private script he was handed as a teenager, which tends to stick harder than anything he was formally taught about respect. Follow with whether he believed it then and whether he still does.
When did you first realize women move through the world differently than you do?
Why ask it
Ask for one moment, not an opinion: a sister texting that she got home, a classmate talked over, a walk at night he had never thought twice about. Having no moment at all is an answer too, about how closely he has been watching.
What has a woman told you about her ordinary day that genuinely surprised you?
Why ask it
The answer shows how much the women in his life confide in him. Listen for whether he took what he heard as information or filed it away as an exaggeration.
What do you think women get wrong about men most often?
Why ask it
The correction he reaches for marks where he feels most misread, which is usually the thing he wants credit for and rarely gets. Letting him air it also means the harder questions do not land on someone already braced.
What is something you wish women knew but nobody says out loud?
Why ask it
Leave this until late, because early on the answer will be a joke. Given a warm room and some patience, this is where the actual conversation happens.
Going deeper
Have you ever stayed in something too long because ending it felt worse?
Why ask it
Save this for when the group is warm, because the honest answer is not a funny story. Most people have done it and few have said it out loud.
What did a past relationship teach you that you would not have learned otherwise?
Why ask it
Framing it as a lesson rather than a post-mortem avoids the bitter version of this story. Someone who cannot name anything has usually not thought about their own part in it.
How do you feel when a woman earns more, knows more, or outranks you?
Why ask it
Almost every guy says he wants an equal. The felt reaction is a separate thing, and it only shows up when she is promoted first or knows the subject better than he does. The pause before he answers is usually the honest part.
Has a woman ever told you that something you did made her uncomfortable, and what did you do with that?
Why ask it
This asks about accountability without accusing him of anything. Notice whether he remembers her discomfort or only his own embarrassment, and whether anything changed afterwards. Ask it in private, never in front of a group.
What have you done, or not done, when another man spoke badly about a woman in front of you?
Why ask it
Opinions cost nothing in private and a lot in a group of men, so this asks what his have cost him. The words "or not done" matter: an honest account of staying quiet is worth more than a hero story.
Which belief about women did you hold at twenty that you have since thrown out, and what changed it?
Why ask it
You are looking for evidence that he can change his mind, and the cause tells you what reaches him, usually a person or a consequence. With someone younger, swap twenty for a few years ago.
If the women closest to you described how you treat women, what would they say that would be hard for you to hear?
Why ask it
Save this for last, because asked early it plays as an accusation. A guy who names something concrete, such as his temper, his attention or how he talks when he is tired, has heard it before and let it in.
Making This Conversation Work
Practical guidance for the conversation itself
Where These Land Best
A Car, a Walk or a Late Table
These questions work in situations where nobody is looking directly at anybody. A group in a car or standing around a grill answers far more honestly than the same group in a circle of chairs, and a guy who goes quiet across a restaurant table will often talk freely on a two hour drive.
Group Questions and One-Guy Questions
Icebreakers, Making a move and most of Attraction are built for a table of friends. Views on women and Going deeper work better with one guy, where he is not performing for anyone and nobody is keeping score.
Go in Order
The icebreakers are stories and jokes, and the last two groups are not. Jumping straight to the serious ones gets a deflection, because nobody has warmed up yet.
Ask About His Life, Not About All Guys
"Why do guys do that?" invites a defence of half the population. "When did you last do that, and what were you thinking?" invites a story. He is one person with one history, and that is all he can speak to.
Answer Them Yourself
Take your turn on each question rather than running the room. A conversation where one person only asks turns into an interview within about five minutes.
Let the Silence Run
On the serious questions the honest answer usually arrives a few seconds after the polite one. Resist filling the gap or offering him a nicer option, and do not agree so quickly that he stops explaining.
Let a Question Die
If a question falls flat, move on without explaining it or asking again. Rescuing a dead question is what makes the whole thing feel like a worksheet.
Signs the Conversation Is Working
- He gives a specific memory with a place and a year in it rather than a general opinion.
- He revises himself mid answer: "actually, that is not true, what I really mean is..."
- He admits to being wrong about something without you having pointed it out.
- He asks you a question back instead of waiting for the next one.
- He says something he clearly has not said out loud before, then checks your face.
Worth Avoiding
- Do not ask about a specific person who is in the room or nearby
- Do not use a group question to find out something about yourself, ask him alone later
- Skip anything about bodies or numbers, it changes the room and rarely improves it
- Do not let the group gang up on whoever gives the most honest answer
- Do not wince or correct him after his first honest answer, ask what led there instead
- Do not ask when what you want is a verdict on him, he will hear it and start defending
- If someone passes on a question, let it go without comment
- Treat what gets said in the serious questions as private afterwards