Questions to Ask Guys About Girls
Light questions for a group hangout or a long drive, for asking the guys what they notice, how they approach someone, and what they get wrong. They start easy and get more revealing further down.
The questions
Open any question for the note
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. The interesting part is how quickly the group calls out anyone who gives the noble answer.
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.
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 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 worst thing you have ever said to someone you were trying to impress?
Why ask it
This gets the story that the previous question was too dignified to produce. Groups tend to escalate here, which is the point.
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.
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.
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.
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 the nicest thing someone has done for you that they probably do not remember?
Why ask it
This produces the most unexpectedly sincere answer in the set, usually about a small kindness at a bad moment. It changes the tone of the group in a good way.
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.
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.
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.
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.
Have you ever stayed in something too long because ending it felt worse?
Why ask it
This is where the set turns from fun to real, so ask it once the group is warm. 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.
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.
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.
Who in your life gave you your idea of how to treat someone?
Why ask it
This is the closing question because it goes furthest, and it names a person rather than a principle. Whether he points to a parent, a friend or the absence of anyone tells you more than any of the earlier answers.
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.
Go in Order
The early questions are stories and jokes, and the last five are not. Jumping straight to the serious ones gets a deflection, because nobody has warmed up yet.
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 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.
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
- If someone passes on a question, let it go without comment
- Treat what gets said in the serious questions as private afterwards