Uncomfortable Questions to Ask a Guy
Uncomfortable questions to ask a guy you are talking to or dating, for a night when you want to see how he handles being put on the spot. The 53 questions run in the order the conversation tends to go: Warm-up, Embarrassing, His flaws, Exes, About us and Hard ones, so the squirming starts out playful and only turns serious once he has had a few easy wins. Every question has a note on what a good or a worrying answer sounds like or what to do with it, and many say when to back off.
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The questions
Each question, and why to ask it
Warm-up
What's the most embarrassing thing you've done to impress someone you liked?
Why ask it
A fair place to start, because the story is old and he is the only casualty. A guy who laughs his way through it will usually manage the harder groups. A claim that he has never tried to impress anyone earns one raised eyebrow and nothing more.
What's the most embarrassing song you know every word to, and will you prove it?
Why ask it
Naming the song is easy; singing it is the squirm. Four bars sung badly beat any spoken answer, so offer your own guilty song first if he stalls. A flat refusal just means he is still guarding his image, which is fine this early.
What phase did you go through that you hope nobody kept photos of?
Why ask it
Frosted tips, a band shirt era, a chain wallet: nearly everyone has one. If his phone comes out so he can show you, he is enjoying this more than he lets on. Don't go to his friends for the pictures afterward, since the fun is that he chose to tell you.
What's the pettiest thing you've ever been jealous of?
Why ask it
Petty is the word that keeps it light: a friend's parking spot, a cousin's dog that likes someone else better. It also gets him used to saying 'jealous' out loud before the About us group asks about it for real. If what he describes isn't petty at all, stop grinning and listen.
What excuse do you use most to get out of plans, and have you ever used it on me?
Why ask it
The excuse itself is an easy laugh; whether you have been on the receiving end is where he shifts in his seat. 'Once, and I was tired' is a perfectly good answer. Don't hold a trial about the night in question, because the game ends the moment an honest answer gets punished.
What's the last thing you searched for that you'd rather not explain?
Why ask it
Usually it is harmless and ridiculous: a symptom, how to spell an ordinary word, whether some actor is taller than he is. Let him tell you and don't reach for the phone, since a question he answers out loud is a game and a screen inspection is not. Have your own ready, because he will ask.
What family nickname would you pay to keep away from your friends?
Why ask it
He can refuse to say it, and the refusal is half the entertainment. If he does tell you, treat it as a loan. Using it in front of other people is how you lose the next ten honest answers.
What have you lied about for so long that it's now too late to correct?
Why ask it
Small standing lies are funny and nearly everyone keeps one going: a famous movie he claims to have seen, a neighbor's name he never learned, a dish he praised once and has been served ever since. If what comes out is not small, the warm-up is over, so drop the joking tone.
Embarrassing
What's the most embarrassing moment of your life that you still wince about?
Why ask it
This is the plain version and the one he is expecting, so he may have a polished story ready. Ask for the runner-up as well, which is usually less rehearsed and worse. Wince along with him and keep the retelling to yourself.
What's the worst way you've ever been turned down, and how did you get out of the room?
Why ask it
The best versions are told with some humor and no villain. Pay attention to how he describes the person who said no, because 'they were nice about it' and 'they thought they were too good for me' are two very different ways to carry the same evening. Leave it out if he was turned down recently and it still smarts.
What's the worst date you've been on that was mostly your fault?
Why ask it
Anyone can tell a bad-date story where the other person was the problem, which is why 'mostly your fault' is in there. If he can name what he did (arrived late, talked about himself for an hour), he can take a note. A story where every detail still points across the table is one to notice and move past.
Who's the most off-limits person you've ever had a crush on?
Why ask it
He gets to decide how much to admit, and leaving out the name is allowed. The usual answers are a friend's older sister, a best friend's ex or a manager at his first job. Keep it in the past tense: who he has a crush on this month is a different question and not one for a game.
When did you last cry in front of someone, and what did you do right afterward?
Why ask it
Plenty of guys will say when they cried but go quiet about being seen doing it. What he did next is the telling part: did he joke, leave the room, or stay put? If he says never, don't argue, since 'fair enough' keeps the door open for later.
What's something you still can't do that most people learned as kids?
Why ask it
He will squirm more over this than over a wild story, because it is a fact about him today: he can't swim, whistle, ride a bike or knot a tie. The kind response is an offer to teach him or learn it together, not five minutes of laughing.
What did you post or send years ago that you'd erase from the internet if you could?
Why ask it
An old status, a homemade music video, a long public birthday message to someone he dated for a month. If he pulls it up, be kind for at least ten seconds before you laugh. Admitting there is something without saying what counts as an answer, and it isn't yours to go looking for.
What's the most trouble you've ever been in, and who did you have to call?
Why ask it
The scale tells you what 'trouble' means in his world, anywhere from a principal's office to a police officer at the car window. Who he called is a second story, and often the better one. If it turns out to be recent or serious, stop playing it for laughs and ask how it ended.
His flaws
What's your worst habit that I haven't seen yet?
Why ask it
The question takes for granted that there is one, so he can't claim a clean record. The answers worth having are specific and a bit sheepish: dishes left soaking for three days, going silent when he is annoyed. Thank him for the warning, and don't quote it back the first time you see it happen.
What do you do when you're in the wrong and you know it?
Why ask it
Asking for the behavior gets a truer answer than asking whether he can admit fault. 'I go quiet for a day, then I come back and say it' is honest and workable. 'I'm not usually wrong,' said without a smile, is the one to worry about.
What do you judge other people for and then do yourself?
Why ask it
He has to catch himself being a hypocrite in real time, which is uncomfortable for anybody. A quick, laughing answer means he already knows this about himself. Answer it too, because this question is unfair if only one of you confesses.
How long can you stay mad, and what's the longest you've kept a grudge going?
Why ask it
Listen for the unit of time. Hours and days are ordinary; years, told with pride, is worth remembering the next time the two of you argue. Ask what finally ended the long one and who made the first move.
What do your friends tease you about that's a little too accurate?
Why ask it
Friends' teasing is usually the affectionate version of a real flaw: always late, tight with money, never texts back. Him repeating it calmly shows he can hear it. Bristling while he describes the joke means that subject is closed for tonight.
If you had to name your own red flag, what would it be?
Why ask it
People are quick to list red flags in others, and aiming the phrase at himself is what makes him squirm. A joke answer first ('I own too many sneakers') is normal, so smile and ask for the real one. A flaw he is plainly working on is reassuring; one he describes as something a partner just has to live with is worth remembering.
Whose opinion of you matters more than you'd like it to?
Why ask it
A thoughtful pause is a good sign, and a fast 'nobody's' is rarely true of anyone. It might be his dad, an older brother, a former coach or strangers online. Whoever he names, skip the advice on how to stop caring.
What do you pretend not to care about that you care about a lot?
Why ask it
This one tends to get a pause, then a laugh, then the truth: his hairline, the likes on a photo, whether your friends approve of him. Once you know what it is, it is not yours to poke at for fun.
Exes
What's the least dignified thing you've done after a breakup?
Why ask it
Unfollowing and refollowing, keeping the hoodie, one song on a loop, a dramatic haircut: undignified is forgivable and usually funny, and it eases him into a group he would rather skip. Turning up uninvited or spreading stories is not the same kind of answer, and you are allowed to take it seriously.
Are you still in touch with any of your exes, and what does that look like?
Why ask it
A birthday text once a year and a daily chat both count as in touch, so the detail is what you are after. Calm and specific is a good answer. Vagueness, or irritation that you asked at all, is something to raise again on another day, not to chase now.
Is there an ex you still think about, and what brings them to mind?
Why ask it
Thinking about someone is not the same as wanting them back, so a yes is no cause for alarm. A song, a street or a time of year is an ordinary answer. Ask it only if you can hear a name without bringing it up in every disagreement for the next month.
How did your last relationship end, in the version your ex would tell?
Why ask it
Asking for the other version makes him step out of the one he has rehearsed. Listen for at least one sentence that doesn't flatter him. If he can't imagine the other side at all, or it turns into a list of his ex's faults, that tells you more than the story does.
Have you ever ghosted someone, and what would you say if they asked you why?
Why ask it
Plenty of people have an unanswered message somewhere behind them, so the yes is not the interesting part. The explanation is: 'I didn't know how to say it' is honest, while 'they should have taken the hint' puts the work on the other person. Follow up by asking how he would want to be told himself, which is useful to know before you ever need it.
What did an ex say about you that turned out to be right?
Why ask it
Sharp, because it asks him to give a point to someone he may not like. 'I was told I never planned anything, and it was a fair point' is a good answer. 'Apparently I was too nice' gets a smile and counts as a dodge.
How soon after a breakup do you usually start talking to someone new, and where do I fall on that timeline?
Why ask it
It starts as a general question and lands on the two of you. A straight answer, even 'sooner than I should have,' beats a smooth one. Ask only if you are ready to hear that the last one is not far behind him.
Have you ever said 'I love you' without being sure you meant it?
Why ask it
It happens: said back out of politeness, said too early, said to end an argument. What matters is whether he knew at the time and what he did once he realized. If the two of you have already said it to each other, he will look at you before answering, so make it clear you are asking about the past.
Have you ever cheated or been cheated on, and what did you take from it?
Why ask it
Ask it plainly and without an edge in your voice, or you will get a careful answer. If he did it, how he tells it matters more than the fact: owning it and saying what changed is not the same as blaming the situation. If it was done to him, it may still hurt, so let him decide how long the answer is.
About us
Are you talking to anyone else right now, or is it just me?
Why ask it
The one most people in the talking stage want answered and keep putting off. If the two of you have never agreed to be exclusive, a yes breaks no promise, so what you are judging is whether he says it straight. Say where you stand too, since he is owed the same answer.
What did you think of me the first time we met that you've never told me?
Why ask it
You are asking for the unedited version: that you seemed intimidating, loud, bored, out of his league. Hear it as a story about that day and not a verdict on you. If you bristle, he will sand down every answer after this one.
What's something I'm into that you only pretend to enjoy?
Why ask it
Whether it is a show, a restaurant, your playlists or brunch with one particular friend, the answer is good news: you find out where he has been generous, and you can let him off the hook. Taking offense teaches him to keep pretending.
What did your friends really say about me after they met me?
Why ask it
He now has to choose between loyalty to them and honesty with you, and that is the squirm. Accept a summary and don't demand names attached to opinions. When something stings, remember that you asked, and that their first read of you is not his.
What do I do that annoys you, that you've been too polite to mention?
Why ask it
Decide beforehand that your whole reply will be 'okay, good to know.' A small, real answer (you interrupt, you run ten minutes late) means he trusts you with it. 'Nothing, you're perfect' is sweet and also a dodge, so ask for just one.
When have you been jealous over me and said nothing?
Why ask it
A mild, specific answer, like the coworker who kept texting you, is ordinary, and it comes easier if he has already answered the petty jealousy question in the Warm-up. Notice whether his fix is talking to you about it or you seeing fewer people. The second is a separate conversation, and one for daylight, not for a game.
What do you think I'd change about you if I could?
Why ask it
He has to guess your complaint about him, which shows what he is already uneasy about with you. Say so gently when he guesses right. When he names something that has never crossed your mind, tell him, because he has been carrying it for nothing.
What have you told me that wasn't completely true?
Why ask it
Expect a small one first: he didn't love the movie, he never finished the book, he was not 'five minutes away.' Laugh at those and a bigger one may follow. You have to be able to hear the answer without making him regret it, so skip this on a night when you are already annoyed with him.
What have I said that hurt more than I realized?
Why ask it
Most people are carrying one of these and would never raise it unprompted. When he tells you, hold off on explaining what you meant and say you are glad he told you. If 'nothing' comes fast, leave a pause, since the real answer often arrives a few seconds later.
Where do you see this going, if you had to say it out loud today?
Why ask it
'I don't know yet, but I like where it is' is honest and not a bad answer. What to watch for is a joke, a change of subject, or words that don't match how he has been acting. Ask once and let him come back to it in his own time.
Hard ones
How do you feel about money right now: comfortable, stretched, or avoiding looking?
Why ask it
The three options let him answer without a single number, because you are asking about the feeling and not the balance. When things are getting serious and he still won't go near the subject, bring it up again on an ordinary afternoon.
What about your family would you want me warned about before I meet them?
Why ask it
Framing it as a warning lets him say something true with a joke on top: an uncle who argues, a mom who will ask about marriage, parents who don't speak to each other. Follow his tone. If the joke drops away and he goes quiet, tell him he doesn't have to go further.
When did you last feel like a failure?
Why ask it
He is asked what he has achieved far more often than this, so a recent, specific answer (a job he didn't get, a promise to his mom he broke) takes nerve. Don't fix it or cheer him up too quickly. Ask what that week was like instead.
What are you most insecure about that you work hard to hide?
Why ask it
Ask only after a few lighter answers have gone well, and never with other people around. Height, money, how smart he is, his body, being behind his friends in life: whatever he names, don't rush to call it silly. 'Thanks for telling me' is enough, and it is off limits for teasing from then on.
What's the worst thing you've done to someone who didn't deserve it?
Why ask it
Everybody has one, and the comfortable move is to pick something tiny, so let him choose the size of his answer. Remorse sounds like detail and a lowered voice. The worrying version is told as a funny story with the other person as the punchline.
Is there a conversation you've been avoiding having with someone, and who is it?
Why ask it
Naming the person, whether a father, an old friend or a boss, is often as far as he can go, and that is plenty for one night. Don't volunteer to help him have it unless he asks you to. If the person turns out to be you, ask whether he wants to have it now or pick another day.
What's the secret you've kept the longest, and who else knows it?
Why ask it
He can tell you who knows without telling you what it is, and that is a full answer: 'only my brother' says there is one and who he trusts with it. Don't bargain for the secret or guess at it out loud. If he does tell you, it stays with you, including after an argument and after a breakup.
What do you need from me that you find hard to ask for?
Why ask it
Needing things can feel like weakness to him, which is why this sits near the end. It might be more time alone, more reassurance or a slower pace. Whatever he names, say it back so he knows it landed, and promise only what you will really do.
What are you afraid I'd think less of you for?
Why ask it
The most exposed question on the page, so keep it for a relationship with some history behind it. Whatever comes out, your face in the next three seconds is the reply he is waiting for. 'I'm not ready for that one' is him being honest with you, not hiding.
Which question tonight were you hoping I wouldn't ask?
Why ask it
A closer that hands him the choice of subject, including one you never raised. Sometimes he names a question and then answers it anyway, which is the best result the game can have. If he only names it, thank him and stop, because knowing where the sore spot is counts as an answer.
How to ask uncomfortable questions without turning it into an interrogation
Practical guidance for the conversation itself
Before you start
Say what the game is
Tell him up front: these are meant to be awkward, he can pass on any of them, and you will answer whatever he answers. An uncomfortable question that arrives out of nowhere feels like an accusation. The same question inside a game he agreed to play is fun.
Trade answers
The fairest rule is that you answer every question you ask, either first or straight after him. It stops the evening from becoming an interview, and going first shows him what an honest answer of the right size looks like.
Give him passes
Agree on two or three passes each, no explanation required. People answer more freely when they know there is a way out, and where he spends his passes tells you something without him saying a word.
Pick the room
Warm-up and Embarrassing survive a table of friends. From His flaws on, the questions need the two of you alone, unhurried, with phones face down. None of it belongs in the middle of an argument, or late on a night when either of you is tired or already upset.
Over text
The first two groups work well by text, where the long pause before his reply is half the fun. The later groups lose their tone in typing and leave a written record he may wish he hadn't made, so keep those for when you are in the same place.
Working through the groups
Start where it is funny
Warm-up and Embarrassing stories are old and cost him very little. Get three or four of them out, with both of you laughing, before you go anywhere else. If he isn't enjoying those, the groups below will not go better.
Go down one group at a time
His flaws is about who he is today, Exes about what came before you, About us about the two of you, and Hard ones about what he keeps to himself. Jumping from his worst haircut to whether he has cheated feels like a trap. Each group earns the next.
A few, not the whole page
Six to ten questions fill an evening. Choose the ones whose answers you really want and let the others go. Reading down a list in order makes any guy feel processed.
Match it to how long you have known him
A few weeks in, stay in the first three groups, with one of the lighter Exes questions at most and, if you need to know, whether he is talking to anyone else. If you have been dating a while, About us is the center of the page. Hard ones are for someone who already has reason to trust you with the answer.
Reading his answers
What a good answer sounds like
Specific, a little sheepish, and with him doing something in it and not only having things happen to him. It doesn't have to be polished. A halting true answer is worth more than a smooth one.
What is worth noticing
One dodge means nothing. A pattern does: every story has someone else to blame, exes are described with contempt, he is angry at being asked at all, or the jokes never give way to an answer. You don't have to rule on it tonight. Keep it in mind and see whether it shows up again.
Discomfort is not guilt
Squirming, laughing, stalling and looking at the ceiling are what the game is for, and they don't mean he is hiding something. Some people need a full minute to find a true sentence. Don't treat his face as a lie detector.
Don't keep score
Whatever he tells you stays out of later arguments and away from your friends' group chat. The first time an answer comes back at him as ammunition is the last time you get a true one.
When to back off
Signs he has had enough
His answers get shorter, he stops asking you anything back, the jokes go flat, or you get 'I don't know' three times running. Go back to a Warm-up question or call it a night. Pushing past that point gets you resentment, not honesty.
How to let him off
'Pass accepted' and a grin is all it takes. Go on to a lighter question, or answer the one he skipped yourself to show it can be done. Don't ask why he is passing, and don't circle back to it an hour later. A pass that gets questioned is no pass at all.
If something heavy comes out
Put the game down. Listen, thank him for telling you, and ask whether he wants to keep talking about it or change the subject. This is no moment for the next question on the list, or for advice he didn't ask for.
When he turns the questions on you
He is allowed to, and the same rules hold. If one of his is too much for you tonight, use a pass of your own. Seeing you do it is what convinces him the passes are real.
End on an easy one
Don't leave the heaviest answer of the night hanging as the last thing said. Finish with something from the Warm-up, or tell him which of his answers you liked hearing most. He should walk away glad he played.