Dirty Questions to Ask Your Boyfriend
Twenty questions about how it feels rather than what happens: what he notices when you walk in, what makes him feel wanted, what he likes and worries is strange, and what he wants to hear afterward. Suggestive rather than explicit, and written for adults in an established relationship.
The questions
Open any question for the note
What goes through your head when I walk into a room?
Why ask it
An easy opener that asks for a reaction rather than a preference. If he has never described it, the answer is usually more specific and less smooth than either of you expects.
What is the first thing you want to do when we are finally alone?
Why ask it
The word finally sets up anticipation and gets a concrete answer. Notice whether the reply is about touch, talking, or just the relief of nobody else being there.
What do you notice about me that I probably do not notice about myself?
Why ask it
This produces the compliments people never think to give because they assume you already know. Expect a habit or an expression rather than a feature.
What is something I did once that you wish I would do again?
Why ask it
Once is the useful constraint, because it isolates a specific event rather than a general preference. Whatever he names is a request that has been sitting unspoken.
How do you like being kissed when we have not seen each other all week?
Why ask it
Contexts change what people want, and absence is one of the few that almost everyone has an opinion about. It is also easy to act on immediately.
What do you think about when you are on your own and thinking of me?
Why ask it
Direct without demanding graphic detail, so he can answer at whatever level he chooses. A vague answer here often just means he has never tried to put it into words.
What makes you feel most wanted, and what makes you doubt it?
Why ask it
The doubt half is the one worth waiting for and the one people leave out. Answers there tend to be about ordinary weeks rather than anything dramatic.
What is the difference for you between wanting me and missing me?
Why ask it
Forces a distinction most people have felt and never separated. It tends to explain why some nights apart feel fine and others do not.
How do you like me to let you know I am interested?
Why ask it
Signals get missed for years because both people assume theirs are obvious. Ask for the actual gesture, and ask whether he notices the ones you already use.
What is the sexiest thing I have said to you?
Why ask it
Words are easier to repeat than anything else, so the answer is immediately usable. If he cannot remember one, that is worth knowing too.
What do you want me to do when you have had a terrible day?
Why ask it
Desire and comfort get tangled and people want opposite things here. Finding out whether he wants to be left alone, held, or distracted prevents a recurring misread.
What do you like that you worry is strange?
Why ask it
Naming the worry is what makes the answer possible, and it usually turns out to be entirely ordinary. Your reaction in the next three seconds decides whether he tells you anything like this again.
How do you feel about being watched?
Why ask it
Short, open, and it splits people cleanly. The answer covers everything from lighting to mirrors to being looked at across a room, so let him decide what it means.
What part of your body do you want more attention paid to?
Why ask it
Men are rarely asked and often have a clear answer. If he says he does not mind, ask instead which part he thinks you overlook.
What would you want me to whisper somewhere we should not be talking?
Why ask it
The setting does the work and keeps it playful rather than clinical. It also gets you an exact phrase, which is more useful than a theme.
What is something you want that you have been waiting for me to bring up?
Why ask it
People wait a surprisingly long time for permission that was always available. If there is something here, it is the most valuable answer in the set.
What would make tonight one you actually remember?
Why ask it
Practical and time-limited, which makes it easy to say yes to. Answers are often much smaller than the question suggests: an early start, no phones, a locked door.
What do you want to hear afterward?
Why ask it
The minutes after are usually unplanned and matter more than people admit. Reassurance, quiet and being held are the usual answers, and they are not interchangeable.
What would you tell me if you knew I would not get self-conscious about it?
Why ask it
Names the reason he might be holding back, which is often your reaction rather than his nerve. Answering this well means listening without defending yourself.
What is something about us you would not change for anything?
Why ask it
A closer that sends the conversation out warmly after the more exposing questions. It also tends to name the thing worth protecting when life gets busy.
Setting these up properly
Practical guidance for the conversation itself
When to have this conversation
Not in the middle of anything
Questions about what he likes and worries about land badly mid-encounter, where any answer feels like a performance review. Have them beforehand, or on a walk, or in a car.
Not after an argument
The same words carry a completely different charge when there is something unresolved. Sort the argument out first, or the answers will be about the argument.
Pick two, not twenty
A couple of questions in an evening leaves room to actually talk about the answers. Working down a list makes it feel administrative.
Go second
Ask, then answer the same question yourself before he does if he is hesitating. Hearing your version gives him a shape to work with.
Listening to the answers
- Do not fill the silence. The second sentence is usually the honest one and it arrives after a pause.
- Ask for the detail rather than the category. When, where, and what it felt like beat any further new question.
- Say thank you to a disclosure before you say anything else. It costs a second and it decides whether there is a next one.
- If an answer stings, note it and come back tomorrow. Reacting live turns his honesty into a mistake he made.
- Do one thing about one answer within the week. Nothing encourages further honesty like evidence that it changed something.
If he cannot answer
Some men have never been asked any of this and genuinely do not have words ready, which reads as evasion and usually is not. Try the negative version, which is easier: what he would not want, or what he does not like being asked. Offer two specific options instead of an open question. Or leave it entirely and mention it again in a fortnight, since these answers often surface days later in the car. What does not work is rephrasing the same question three times in one evening, or treating a shrug as proof that something is wrong. If nothing at all can be discussed after several attempts, the difficulty is about talking rather than about desire, and that is the more useful thing to raise.
What goes wrong
Fishing for reassurance
If what you actually want is to hear that he still finds you attractive, ask for that directly. Using these questions as a proxy produces answers you will not believe anyway.
Turning an answer into a rule
He liked something once in one mood. Treating it as a standing preference is how couples end up repeating something neither of them enjoys.
Keeping score
Counting whose answers were more generous or more revealing turns the conversation into a competition. Some questions will suit one of you more than the other.
Bringing it up later as evidence
Quoting an answer back during a disagreement ends this kind of conversation permanently. Anything said here stays out of arguments.