Thursday, June 20, 2024

8 Essential Questions To Ask Yourself Before You Have Sex With Someone

No question is off limits, and all questions will remain anonymous. This week’s topic: questions to ask yourself 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: questions to ask yourself before you have sex with someone.

Q: I saw your article a while back on questions you should ask someone before you have sex with them, and I try to follow the advice. I guess what I’m wondering is, are there any questions I should just be asking myself? Like, the other night I slept with someone I was feeling sort of ambivalent about, but it had gotten so far that I felt like I kind of owed him or something. I’m wondering if you have any tips for checking in with yourself in moments like this.

A: The situation you describe is so relatable, I think especially for women. Often, it can be difficult to separate what we actually want from our fears of seeming mean or “like a tease.” Here are some tips for questions you can ask yourself when you’re deciding in the moment whether to sleep with someone. (I am writing this as much to remind myself as I am for you — so please don’t be hard on yourself if you ever struggle with this.)

Do I Feel Comfortable Talking To This Person About Safe Sex?

In the article you referenced, I give a list of questions I think you should ask someone before you have sex with them, like when they’ve last been tested and whether they have any STDs. Take some time to review those, and in the moment you’re deciding, ask yourself not only whether you know the answers to these questions yet, but also whether you feel comfortable brining them up in the first place.

If you already had the conversation, do you trust their answers? Did you feel they were appreciative of your asking, or did they seem weirded-out and threatened? Someone worth sleeping with shouldn’t make you feel awkward about asking about their STI status or about safe sex practices. If they were cool about it and you felt very weird about asking anyway, it could also be a sign that there isn’t a lot of comfort for you in the dynamic yet, and you might be jumping the gun.

Will It Bother Me If I Find Out They Are Sleeping With Other People?

Another question I suggest you ask a potential partner is whether they are currently sleeping with anyone else. A question you can ask yourself, however, is whether you’d be OK with finding out they are sleeping with other people after you have sex.

If so, it’s important to communicate before you have sex what you would expect to know from them. Would you like to know about any new partners they have after you sleep together? Would you like to become monogamous after sleeping together? These are all important things to know going in, because once you have sex, things can get a lot more complicated.

Do I Trust This Person To Be Honest With Me?

If you were to ask the person to answer any sensitive questions about their health, sexual preferences, or how many partners they have, do you trust they are giving you the whole truth? Do you sense that they would keep telling you the whole truth? Trust your gut on this one. If you doubt their honesty, that’s a sign it might be too soon.

If We Sleep Together & They Ghost, Will I Regret This?

Unfortunately, this is always a possibility, because people are rude. Even if it seems highly unlikely, if this worst-case scenario were to happen, would you regret your decision to sleep with them? Or would you know that you were doing it because you really felt like having sex and it was a genuine expression of your own desires?

I find I only regret sexual actions when I feel like I wasn’t being true to myself in some way, or was acting for other people’s benefit instead of my own. Which brings me to…

Am I Doing This Because I’m Worried About Seeming Like “A Tease”?

This is such a hard dynamic to avoid — especially when you’re a woman raised to think you owe men something once you “let” things get beyond a certain point. Are you about to have penetrative sex only because he just went down on you for half an hour and you feel “bad,” even though you’re not really ready? Time to communicate that and put the brakes on things. I don’t care if you brought him into your room and he gave you an hour-long massage. You never owe anyone sex, and the idea of “being a tease” is really often just coded language for “being a woman who says no when she doesn’t want sex.” All you owe someone is your open communication and honesty.

If you’re having this dialogue in your head and are unsure how pressured you’re feeling, tell them! How they react will speak volumes about their character. (Just beware feeling like you “owe” someone a reward for good behavior if they are cool about not pressuring you.)

Am I Only Doing This Because I Need An Orgasm Right Now?

Sometimes we have sex before we’re ready  just because we’ve been doing other stuff for a few hours, and we’re horny. If this sounds familiar, ask yourself this question in the moment. If you are just having sex because you want an orgasm but aren’t really ready emotionally (been there) is there another lower-risk activity you can suggest, like mutual masturbation? That way, there will be some closure and release to the night without your feeling like you’ve reached the point of no return by default.

Am I Doing This For Reasons That Are Kind To This Person And Myself?

Are you just having sex because you’re trying to get over an ex? To prove to yourself you’re desirable? Because this person seems hot but boring enough that you won’t catch feelings? Whatever the reasons may be, it’s important to check in with yourself that they are kind to both yourself and your potential partner. It’s totally OK if you’re about to have sex for less-than romantic reasons, so long as both people are on the same page and the attitude is one of mutual respect.

Do I Feel Safe, Respected, And Like I Want To Give Enthusiastic Consent?

This is probably the most important item. You should feel all of these things before you have sex, even if it’s casual. Do you want to give a clear and enthusiastic go-ahead, or are you allowing yourself to be swept up in someone else’s preferences? There’s nothing wrong with being a little submissive at heart, but you should be clear that what you’re about to do is what you actually want to be doing — not just something you’re doing to accommodate someone else. I repeat: you don’t owe anybody anything besides your honesty, kindness, and communication. Period.


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