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I came across this “List of Dirty Questions to Ask Your Partner” in an online article. Obviously, this type of content immediately caught my attention. However, when I read them, I found some problems… well… we can say they need some adjustments or deeper nuances.

Not only that one List. I noticed many similar posts have similar issues.

This is one of them… but I added some of my own thoughts.

What’s your dirtiest sexual fantasy?

First of all, this is a great question, but it’s not something you would ask someone you just met. So, while I would definitely ask this question, I would split this list into two groups:

green (Just for fun. Or if you want intimacy this is necessary)
Yellow (Requires more trust or sensitive topics)

This is also due to A dynamic between two (or more) people. If this is a drinking game between friends, someone wants to get to know their partner/lover better, or you’re chatting with someone who is more sexually open-minded – This may change the color coding.

For example: I’m more open about my sex life and strangers can ask me a lot of “code yellow” questions without feeling awkward. However, if a stranger approaches me in a club and starts chatting me up, “Hey, what’s your favorite sex position?” I might be put off.

69 Sex Questions I Found on the Internet

How many people have you slept with? I don’t like this wording. It’s asked too early and feels like an interrogation question. It can also make people feel unsafe. A better way to ask it is, “How do you feel about your sexual experiences?”
Where is the weirdest place you’ve had sex? It’s fun and promotes more communication.
What’s your favorite part of my body? Yes. Great – free gift.
Have you ever had anal sex? This is an important question because anal sex isn’t for everyone. If a woman were to ask a man for anal sex, she might be more cautious. But it’s still a good question.
If you could choose what you are wearing right now, what would you choose? Well, I think I’ll rephrase it like this, “What sexy clothes do you imagine me wearing?”
What part of your body do you like to be touched the most? Yes. I like it very much.
When was the last time you had an obscene dream? Sure. It’s interesting. But not everyone remembers dreams very well. You can adjust it. “What’s the dirtiest dream you’ve ever had?” – This is different from fantasy, it’s just for reference.
If you could have sex anywhere in the world, where would you choose? I loved this. There is so much to say and the details reveal the deepest parts of a person.
When was the first time you had sex? Fair to ask.
What was the best sex you’ve ever had? I would answer about the details of the sex. Not who did it. Don’t risk making it a competition. Someone may not want to hear about how great your ex was in bed.
What is your favorite position? Yes, this is a standard question everyone should ask. Especially if a fast connection is likely to occur.
Have you ever been caught having sex? It could be an interesting conversation.
Do you watch porn? Some people are sensitive to pornography. Be aware of what you are getting into.
What type of porn do you watch? If the respondent is willing to talk about that, then it’s a fair follow-up question.
How often do you masturbate? This may be personal for some people. Wait until the right time to ask.

Image source: Pexels

Name a sex position you’d like to try. I’m on the fence about this. Things could go either way. If you’re looking for a new experience, this is a good discussion.
Do you prefer to give or to receive? You need to be asked if you want to play – whether you are gay, or a homosexual, or whatever.
What was the best orgasm you’ve ever had? It would be great if it was about orgasms and how to orgasm again. Rather than who gave you the orgasm.
Have you ever gone skinny dipping? It’s an interesting question, for sure. Gentle enough to know if someone is a bit adventurous.
Have you ever slept with your coworkers? This gets more personal. I also think I don’t know… weird? Don’t ask this question at work ahahahaha.
If we were out to dinner and I said I wanted to have sex right now, what would you do? If you knew the person better, it would probably be enthusiastic.
Have you ever sent a nude photo of yourself? As long as you don’t ask for nude photos right away.
If you could sleep with any celebrity, who would you choose? It’s totally okay to ask. It’s an interesting question.
Do you have/have you ever had group sex? Always wait until you know someone at least a little bit before asking this question. Also, if you’re asking this question at a club instead of on a first date… well, you get the idea.
How many times a day do you have sex? This is similar to the question about sexual desire on this list. There’s no harm in asking it, but it gets into the gray area of personal topics.
Are you loud or quiet during sex? This might be important to know if you’re bringing someone home and your neighbors are nosy… or just jerks.
Have you ever tried using food during foreplay? Sure. I can live with that. No harm done.
Have you ever made a sex video? Yes, there are issues on a personal level. Not to mention the anxiety and fear that media information being leaked (whether accidentally or not) can cause.
What is the first thing that makes you sexually attracted to someone? There’s no harm in asking this question. Everyone has something they like.
Would you say you have any fetishes? Some people feel this way but are too ashamed or unwilling to share the truth with themselves, let alone others. Please approach this situation with caution.

When it comes to BDSM, how far have you gone/how far will you go? My take on this question is that BDSM is such a large cluster of topics and practices that it’s hard to answer in general terms. It’s like asking “How accomplished are you at sports?” The question can be answered, but I’d have to dig into the specific sport.
What is your favorite toy? It’s easy to answer and there are lots of equally fun follow up questions. But first make sure you/they are not insecure/shy about sex toys.
Have you ever read erotic novels? This is a great way to test the waters or ask warm-up questions.
Have you joined the Mile High Club? Again, talk about personal issues – there’s nothing wrong with that, but since it involves details about other people, it’s best to ask about it later.
Do you think you can take my panties off without using your hands? Yes. I mean, if the flirting gets intense, sure. But it’s not something that can be asked right away.
Would you say you are perverted? This is a much better way to start a weird conversation than some of the other questions.
Do you like shower sex? Good to know. It’s also safer than having sex in water.
Where is the weirdest place you’ve ever masturbated? The definition of weird varies from person to person. Since you asked the question, don’t judge the answer. Maybe use words like adventurous, interesting, and the hottest.
Do you like being spanked? Another question that makes me hesitate. If you have already determined that the other person is a pervert or a liberal, it is safe to ask early.
What is your most embarrassing sexual experience? This can be very personal and even painful. Be careful.
Have you ever fantasized about someone else during sex? Depending on who you are talking to, this could be seen as an interesting question or some invasion of privacy.
If I caught you masturbating, would you stop or would it end? I don’t like the word “caught” because it makes it sound like you’re doing something wrong. I would rephrase it as “If I catch you…” and that might be funny.
Have you ever had an inappropriate crush? It depends on how one interprets “inappropriate”.
Have you ever cried or fallen asleep during sex? Ugh. Yes, you can cry because the sex was great. Or faint because it was too much. But those emotions can also come from bad experiences.
Do you enjoy eye contact during intercourse? It’s good to know.

Do you like kissing during sex? It is also important to know this.
Do you feel tired after sex? I would say this is a good question to ask. Some people are extremely sleepy after sex and they just can’t help falling asleep. It’s good to let the other person know so it doesn’t take it personally.
How many positions do you think you have tried? Gray area. As long as it’s for a new position or adventure, it’s fine.
How long have you been without sex? This could be related to a bad moment in someone’s life. Please handle it with care.
How high is your sex drive? For some people, knowing sexual compatibility may be important.
What are some surefire ways to get high? Yes, please.
Should you have sex with the lights on or off? Sure, why not?
Do you like to talk dirty? Yes, you need to know this. Because being called a “dirty whore” during sex can have wonderful or horrible consequences. Don’t forget to ask follow-up questions.
Have you ever had sex in a car? Talk about taking an adventure. I can relate.
Do you prefer to be in control or to obey? If you have a kink or are exploring a kink, this is a question worth asking.
Do you prefer a one-night stand or a long-term sexual partner?
Yes, this is definitely a personal question. It’s not a bad question, just not appropriate to ask on a first date.
Do you prefer to be on the top or the bottom? This isn’t just about power dynamics around sex. It can be about body issues, and understanding those issues can be good for everyone.
What would you rather do in bed? It’s always good to know.
What is your favorite time of day to have sex? This may sound strange, but it’s important — not only for sexual compatibility but also for timing.
Rough or romantic? Can’t it be a little bit of both? Not everyone is the same. People want different things at different times?
A short meeting or a long one? Again. Why not both? Yes, people have preferences, and it’s good to find out what they are, but be sure to ask the right follow-up questions so you can better understand the “why.”
What is your favorite part of foreplay? It is necessary. It is necessary to ask this question. And give more.
Will you dress me in bed? Depending on your personal comfort level, you can also request something directly for yourself.
Where do you like to be kissed the most? Everywhere! I mean… good question.
Do you like sexting? It’s good to know. Some people may not be able to attend due to work or other reasons.
What’s the best thing about our sex life? You will ask this question when you have been having sex for a while. Make sure you ask this question.
What’s the shortest time you’ve ever taken to orgasm? What’s the longest time you’ve ever taken to orgasm? It’s fun, but some women don’t orgasm — or at least not noticeably so. Keep it light unless you and the other person want to spice things up.
How are you going to make me orgasm? I would also rephrase this sentence to, “Describe when/where/how you would like me to orgasm.” Make it more like a fantasy or role play and less about the physical ending.

I bet you’ve thought to yourself more than once by now, “No, I wouldn’t ask that question so soon.” or “What’s wrong with this question?” I’ll say it again, It all depends on the circumstances of the conversation. Just use good judgment and know if you are crossing a line.

Are these good questions? YesI have asked all of these questions myself. Be sure to use them and other examples from other lists – But don’t use it as a first date checklist, inquiry, etc.

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What are your thoughts on these sexual issues? Share them in the comments!