Questions to Ask a Guy Before Sleeping with Him
For anyone deciding whether to sleep with someone and wanting the practical conversation first. These 20 questions cover expectations, exclusivity, testing, contraception, boundaries and how to stop.
The questions
Open any question for the note
Are you seeing anyone else right now?
Why ask it
Ask plainly and early, because it is the fact you most need and the easiest one to get lost in softer phrasing. A person who answers with a question about what you mean by seeing is usually buying time.
What are you hoping this turns into, if anything?
Why ask it
The useful version of this is open, not leading, so he is not just agreeing with the answer you signalled. Someone who genuinely wants something casual will usually say so if you have not made that costly to admit.
Would you be fine with this staying casual, and would you be fine if it stopped after tonight?
Why ask it
Both halves matter, because people who say casual sometimes mean they want more without the label. Discomfort with the idea of it ending once is worth knowing before rather than after.
Are we exclusive, or should we both assume we are not?
Why ask it
Assumptions here almost never match, and the mismatch is usually discovered painfully. Naming the default out loud costs one awkward sentence and prevents a much worse conversation.
When were you last tested for STIs, and what were you tested for?
Why ask it
The second half is the one that matters: standard panels often skip herpes, and some skip syphilis or hepatitis. Anyone who has been recently tested can answer this easily, and a person who treats the question as an insult is telling you how they handle inconvenient responsibility.
I get tested regularly and here is when I last did. Would you be willing to get tested too?
Why ask it
Offering your own status first turns this from an accusation into a shared standard. Willingness to go and get tested, rather than just insisting he is clean, is the actual signal.
Are you okay using condoms every time, including if we do this again?
Why ask it
Agreement in the moment sometimes evaporates the second or third time, so it is worth setting as an ongoing condition rather than a one-off. Any attempt to negotiate this down is the clearest possible information about how he treats your limits.
Do you know anything about your own risk history I should know about, like a diagnosis you carry?
Why ask it
Many manageable infections are lifelong, and plenty of people disclose honestly when asked directly. What you learn from the answer is both the medical fact and whether he volunteers difficult information.
What would we do if a condom broke or I turned out to be pregnant?
Why ask it
Asking now surfaces a real disagreement about pregnancy options while it is still hypothetical. Someone who refuses to engage with the question at all is unlikely to be steady if it happens.
Is there anything you do not want done to you?
Why ask it
Consent runs both directions, and men are rarely asked this. His answer also tells you whether he can name a limit at all, which predicts how he will hear yours.
Here are the things I am not up for. Are you clear on those?
Why ask it
Stating your own limits before anything starts is far easier than stopping mid-way, and it gives you a clean reference point later. Watch for anything that sounds like negotiation rather than acknowledgement.
If I say stop, what happens next?
Why ask it
The correct answer is short and boring: everything stops, no explanation needed. Sulking, asking why, or promising to be careful instead of stopping are all answers that should end the evening.
Do you want anything specific, and is there anything you would rather I did not assume?
Why ask it
Framing it as a preference rather than a yes or no question makes it easier to answer straight, and it draws out the assumptions he was otherwise going to act on without mentioning. The second half lets you rule something out now instead of having to stop him partway through.
Have you told anyone about me, and do you plan to?
Why ask it
This gets at privacy and discretion, which matter more if you share a workplace, a friend group or a small town. Someone who plans to narrate the evening to a group chat is worth knowing about beforehand.
Do you take photos or video? I want to be clear that I do not consent to that.
Why ask it
Saying it explicitly removes any later claim of misunderstanding, and in many places recording without consent is a crime. His reaction to being told no on this is the point of asking.
Are you sober enough to be making this decision, and am I?
Why ask it
Naming the alcohol out loud interrupts the drift that leads to regret on either side. If either answer is no, the useful outcome is a rain check rather than a debate.
Do you want to stay over, and are you comfortable saying if you would rather not?
Why ask it
Deciding the logistics in advance avoids the most awkward stretch of the night. It also gives him permission to be honest instead of leaving abruptly at two in the morning.
What would you want to happen the next day? Text, nothing, something else?
Why ask it
Most of the hurt around casual sex happens in the following 24 hours, not during it. Agreeing on a plan, even a plan of no contact, means neither of you is reading silence as a verdict.
If one of us wants to stop this arrangement, how would you want that said?
Why ask it
Deciding on an exit while things are still friendly makes it possible to actually use it. A person who dismisses the question as unnecessary is often the one who ghosts.
Is there anything you would want to know if you were me?
Why ask it
Asked at the end, this gives him one clean opening to disclose something he has been sitting on, whether that is a partner, a diagnosis or an intention. What he does with the opening tells you as much as what he says.
Having This Conversation
Practical guidance for the conversation itself
When and How to Ask
Ask Before the Bedroom, Not In It
The testing, exclusivity and contraception questions work over a drink or by text earlier in the day. Asked half-undressed, they get answered however keeps the moment going.
Text Is a Legitimate Format
Written answers about testing, other partners and condoms are easier to ask for and harder to walk back. If a question feels too heavy to say out loud, sending it is not cowardice, it is just a different channel.
Say Your Own Answer First
Lead with your last test date, your own limits, your own expectations. It makes the exchange mutual rather than an inspection, and most people match the level of directness they are given.
Watch the Reaction, Not Just the Words
Anyone can say the right thing about consent. Irritation at being asked, jokes to move past it, or flattery deployed instead of an answer are all data, and they are more reliable than the content.
Practical Things Worth Sorting Out
- A standard STI panel does not automatically include herpes, so ask what was tested
- Recent exposure may not show up yet, which is why condoms matter even with a clean recent result
- Bring your own condoms rather than relying on his supply or his sizing
- Know where you would get emergency contraception locally and how fast it needs to be taken
- If you are on hormonal birth control, check whether any medication you take reduces its effectiveness
- Tell one friend where you are going and who you are with, especially if you have not met in person before
- Meet somewhere public first if this started online, and keep your own transport home
Reasons to Stop the Plan
- Any pressure to skip the condom, including at the last moment
- Treating the testing question as an insult or a mood killer
- Refusing to answer whether he is seeing anyone else
- Answering the stop question with anything other than everything stops
- Pushing past a limit you already stated, even lightly, to see if it holds
- Either of you too drunk to be deciding clearly
- A feeling you cannot justify. You do not owe anyone a reason, and leaving costs you nothing you will miss