Wednesday, March 22, 2023

8 Questions You Need To Ask Before You Have Sex With Someone

No, but really — how does a person have better sex or a better relationship? The Fresh Toast has enlisted Rachel Krantz, a sex writer and proud canna-enthusiast, to help readers out with some answers as its sex columnist. No question is off limits, and all questions will remain anonymous. Please send your sex and relationship inquiries to Now, onto this week’s topic: nine questions you should ask before you have sex with someone.

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Q: Lately, I’ve been dating around. I’m looking for a long-term relationship eventually — well, I’m open to it, but I also don’t need one. I’ve been enjoying playing the field a bit and sleeping around a little more than I used to. That said, I want to be sure to do it in a way that isn’t dumb or disrespectful, or dangerous. Are there any questions I should ask someone before I sleep with them so I don’t end up regretting it later — or hurting their feelings?

A: Hey — great question! The short answer is, yes. Whether you’re looking for a relationship or not, there are certain things that should be communicated with anyone before you have sex. Here are my tips for nine questions you should ask someone before you sleep with them.

What Are You Hoping For From Me?

This is a great way to not only establish consent, but also to make it clear what the other person’s expectations are. If they answer honestly, you’ll know more clearly if they are expecting sex to mean something serious, or whether they’re also looking to keep things more casual. If their answer is “…Well, I don’t know, what do you want?” be as honest with them as you can. It isn’t kind to lie, even if you’re saying what you think they want to hear. If you want to sleep with them, but aren’t looking for anything more, you need to be upfront about that. Likewise, if you are hoping sex will mean a relationship, be upfront about that too. Better awkward now than later.

When Was The Last Time You Got Tested?

This one is crucial. Remember: a clean STD test doesn’t mean you shouldn’t use protection. For one, people sometimes unfortunately lie, and for another, many STDs don’t show up in test results until three months after exposure. So, even if they got tested last month (and that would be a good sign they take care of themselves for sure!), if they’ve had sex with someone new in the interim or in the couple months before they were tested, they could still be carrying something the test didn’t pick up. If they can’t remember the last time they got tested, this is a red flag, and you might want to request they do that before you go any further. (Here’s a list of STDs you can still get with a condom, for reference).

Do You Have Any STDs/Have You Recently Had Any STDs I Should Know About?

Yes, it’s uncomfortable to ask — but you should. I once had a guy not disclose he had genital herpes until he was naked and we were about to have sex — not cool, to me. That experience taught me I need to ask this question before it gets to that point. You also might want to check if they’ve recently had anything that isn’t on an STD test but is still sexually/socially transmitted (scabies, lice, bedbugs, all that fun stuff). Better to ask then end up sorry.

What Would Having Sex Change For You About Our Relationship?

If you suspect the person you’re sleeping with has more or less feelings than you do — or might want something else — this is important to get on the table. Again, it’s crucial you not tell them what they want to hear in response, but the truth. If you know sex will not mean you want to date them more seriously, you need to be upfront about that. If you know it tends to make you expect them to be more serious, or to call the next day, be clear about that too.

Are You Sleeping With Anyone Else Right Now?

Again, it might seem awkward, but if you’re going to sleep with someone, you have a right to know if they’re sleeping with anyone else, if they’re using protection, and whether they know what that person’s STD status is. If they say no, they aren’t, you can also ask that they let you know if that changes (before you would have sex again). This is also a good time to have a conversation about whether you expect having sex to mean monogamy from that point forward. Don’t take it for granted that they do or don’t.

Is There Anything You Especially Like In Bed?

Finally, a sexy question! This is a great way to get an idea of what the other person likes — maybe they’ll tell you they love receiving oral, or being held by the wrists. If they are into power play, be sure to also get their safeword and to communicate your boundaries with them ahead of time. (Here’s a good guide on how to do that.)

May I …?

This is a great question to ask every step of the way. If you’re wanting to move from making out to touching her breasts or pussy, you need to ask! It might feel weird at first to get affirmative consent, but it’s actually quite sexy. It builds anticipation and trust. Which brings me to perhaps the most important question on here…

Do You Want To Have Sex? 

CONSENT CONSENT CONSENT. Even if she’s bucking her hips, or he’s hard, you need to get it. Get a clear, affirmative and enthusiastic “yes” — otherwise, please don’t keep going. If you assume they’re down just because they haven’t said no, you may end up committing sexual assault, and that would be a horrible situation for everyone involved. The absence of a no is not a yes. (For more on what constitutes affirmative consent, check out this great guide, or the video above).

Do You Have Condoms/Lube/Any Toys You Like To Use?

If you get an affirmative yes, this is a great follow-up question. Don’t have sex before the STD-prevention and birth control are squared away — but you can also score major points by asking about lube, or anything else, like sex toys, that might ensure they have the best time possible.

Remember, communication is sexy. Even if it doesn’t feel like it in the moment, not only is it the right thing to ask these questions — but it will ensure you both have a better time, knowing you’re safe, and that expectations and boundaries are clear.




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I thought a big dick was supposed to be a good thing! I really like him, and I feel bad that he can’t always be all the way inside me. Do you have any tips for having sex with big penises without hurting yourself?

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