Dirty Questions to Ask Boyfriend
Twenty questions about fantasies and what your boyfriend wants to try, written to be traded back and forth rather than asked one way. They move from things he can answer easily toward plans and limits. For adults in a relationship, and better with a rule that either of you can pass.
The questions
Open any question for the note
What is your favorite thing I have ever started?
Why ask it
A gentle opener that gets him talking about you being the one to initiate. The answer often reveals that what he liked was the confidence rather than the act.
What would you pick if we swapped who was in charge for a night?
Why ask it
The framing as a swap makes it playable rather than a request. Whether he wants more control or less of it is worth knowing before either of you assumes.
What is a fantasy you have never said out loud to anyone?
Why ask it
Expect a pause and possibly a smaller answer than the question implies. The first one offered is usually a test to see how you react, so react well and wait.
Where, other than a bedroom, have you thought about?
Why ask it
Place is easier to admit than an act, which makes this a good route into the same territory. It also surfaces practical fantasies you could actually arrange.
What have you read or watched that you thought about for days afterward?
Why ask it
Borrowed material carries less exposure than a first-person want, so people answer this honestly. What stuck with him tells you the theme, and the theme is more useful than the scene.
What do you want me to do more slowly?
Why ask it
Almost everyone has an answer and almost nobody has been asked. Pace is the easiest thing to change and one of the least discussed.
What would you like me to say that I do not usually say?
Why ask it
Words are free and specific, and hearing the exact phrasing beats guessing at it. If he cannot name one, ask what he would not want said, which is often easier.
What do you find more appealing than you would admit to your friends?
Why ask it
The gap between what someone enjoys and what they will own publicly is where the interesting answers sit. Give it a moment; the first response is usually a joke.
What is a compliment about your body nobody has given you?
Why ask it
Men are complimented narrowly and often not at all, so this frequently lands harder than expected. Whatever he names, use it later rather than only in the moment.
What would you want to be talked into?
Why ask it
Names a want while keeping the responsibility shared, which is why it gets answers a direct request does not. Take it as an invitation to raise it again, not as consent given now.
What have you always wanted to be asked for?
Why ask it
Flips the usual direction and often reveals he has been waiting to be wanted for something specific. The answers tend to be simpler than either of you assumed.
What is something you want to try that you think I might refuse?
Why ask it
Naming the fear of refusal is what makes the disclosure possible. Whatever it is, thank him for saying it before you answer, because the answer can wait and the goodwill cannot.
What would you want to plan in detail rather than let happen?
Why ask it
Separates spontaneity from anticipation, and plenty of people prefer the second and never say so. A planned answer is also one you can put in a diary.
What have I done that surprised you in a good way?
Why ask it
Positive and specific, and it works as a breather between heavier questions. It also tells you which risks of yours paid off.
What would you want to do if we could not be interrupted for a whole weekend?
Why ask it
The no-interruption condition removes the usual constraint and lets him answer at scale. Notice how much of the reply is not about sex at all.
What do you think I want that we have never done?
Why ask it
Asking him to guess about you is revealing twice over: it shows what he has picked up, and what he has invented. Correct it gently and add the thing he missed.
What would you change about how we usually start?
Why ask it
Beginnings are habitual and rarely examined, and this is a low-stakes way to alter one. Answers about location, timing and who moves first are common.
What is a limit of yours you want me to be clear about?
Why ask it
Asked as a favor to you rather than a warning to him, which makes it easier to say. A person who names a limit is more likely to say yes to other things, not less.
What is something you want that you have been waiting for me to suggest?
Why ask it
Waiting is extremely common and it stalls quietly for years. If he has been waiting, this question is the whole point of the exercise.
What is one thing you would want us to try before the end of the year?
Why ask it
A closer that turns the conversation into something with a date on it. Pick one and put it in the calendar, because unscheduled intentions here reliably expire.
Trading these back and forth
Practical guidance for the conversation itself
How to swap rather than interview
One each, alternating
Ask, answer the same one yourself, then let him choose the next. A one-directional set of twenty questions makes the person answering feel assessed no matter how warmly you ask.
Answer first on the harder ones
For the questions about limits and things he thinks you would refuse, go first. Someone who has just heard your answer has a much easier time producing their own.
Agree that passing is free
Say up front that either of you can skip anything without explaining. It sounds unnecessary until the one question he genuinely cannot answer yet comes up.
Keep it to a handful per evening
Four or five questions is plenty. The rest keep, and a second conversation next month gets better answers than a long single session.
Wanting, saying and doing
- Naming a fantasy is not agreeing to do it. Ask again nearer the time, out loud, every time.
- A no to one item is not a no to the conversation. Say so explicitly, or he will assume otherwise.
- Some fantasies are better kept as fantasies. Ask which kind it is rather than deciding for him.
- If something is a limit for you, say it plainly and warmly. A vague yes that turns into resentment does more damage than a clear refusal.
- Revisit limits occasionally. A boundary set three years ago may not be current, and neither of you will find out unless it is raised.
If he goes quiet
Plenty of people have never been asked what they want and do not have the vocabulary ready. Silence usually means he is looking for words, not hiding something. Offer two options rather than an open question, drop the subject and come back to it in a week, or switch to the easier version: what he would not want, or what he remembers liking. If he says he does not know, believe him, because the answer often arrives days later once the question has had time to sit. What does not help is asking again in the same conversation with a slightly different phrasing, which turns a question into pressure.
What goes wrong
Reacting to the answer you asked for
Even a small flinch after a disclosure ends the honesty for a long time. If you need to react, say you are glad he told you and take your own reaction elsewhere first.
Negotiating in the moment
The middle of an intimate evening is the worst time to bargain over something new. Have these conversations with clothes on and something else to do afterward.
Comparing him to anyone
Bringing an ex into an answer, in either direction, converts a good conversation into a bad one instantly and permanently.
Asking then never following up
If he names something and nothing ever happens, the lesson is that disclosure achieves nothing. Act on one small thing within a fortnight.