How Often Should You Ask For Something? Parts 1 and 2

This piece was originally published on the Blowfish Blog. I never reprinted it here — not for any particular reason, mostly just because I lost interest in the topic after the piece was initially published. But the Blowfish Blog archives are apparently no longer on the Internets, and the original piece is no longer available. So in the interest of completism and making all my published works accessible, I’m going ahead and posting it here.

If you’ve asked for something sexual, and your partner has said “No” — or “No, not now, maybe some other time” — is it okay to ask again?

And if so… how often?

I was inspired to write this by a letter to Scarleteen, the sex advice Website for (primarily) teens and young adults. A 17-year-old girl has a boyfriend who wants to finger her — and he keeps asking for it. He says that he respects her right to say “No”… but he keeps bringing it up. Over and over again. Like, every time they do sexual stuff. She’s made it clear that she won’t be ready for that for a while; she’s told him, “Wait ’till I’m in college and we’ll see.” To which he says “Okay”… and then brings it up again the next time.

Scarleteen’s advice, in a very short oversimplified summary: “Asking for a particular sexual thing every time you have sex is not okay. It’s pressure, and it doesn’t count as taking ‘No’ for an answer.” And in my opinion, this advice is totally sound. Especially for this particular situation. No matter what broad general guiding principle we might come up with for “How often is it okay to ask again for something when your partner has said ‘No’?”, surely “Every single freaking time you have sex” has got to be an unacceptable answer. And when you’re talking to an audience of largely teenaged girls — many of whom have yet to develop strong No-saying skills — that goes double.

But while this one situation does seem to have a clear answer, it does raise some interesting broader questions. So again I ask: If you’ve asked for something sexual, and your partner has said “No” — or “No, not now, maybe some other time” — is it okay to ask again?

And if so… how often?

See, while I strongly agree with Scarleteen’s advice on this particular situation, there was one broader principle they raised about relationships in general that I took issue with:

Ideally, the way a partner should respond to a no is by completely accepting a no.

If they knew it was something they really wanted, and it was only about you not wanting it, they could also respectfully say, “I respect that and want to respect that, but I am interested myself, so if you change your mind, could you just let me know?” In other words, he can voice his wants, but since you have said no, he needs to leave the ball (as it were) in your court, without revisiting the subject unless you put it on the table. After all, you’re both aware of what he wants, obviously: it’s not like he was unclear, either. (Emphasis mine.)

Hm. Once you’ve asked for something, and your partner has said “No” — the ball is then in their court? Forever? You can’t bring it up ever again? Not just this jackass boyfriend with this 17-year-old girl in particular… but anyone, in any sexual relationship?

If that’s what they’re saying… then I have a problem with that.

Here’s the dilemma. Obviously, No means No. That’s a cornerstone of sexual ethics. I hope I don’t have to explain why. When someone says, “No, I don’t want to do that,” you take No for an answer. Period. You don’t force them; you don’t guilt-trip them; you don’t pressure them. You’re entitled to your desires, and you’re entitled to get out of relationships with people whose desires don’t mesh with yours — but you’re not entitled to have any kind of sex you want, with any partner you’re with. No means No. I’m not going to debate that.

But here’s where it gets tricky.

There’s been more than one time in my sexual life when I’ve asked for something that my partner has said “No” to — and I’ve asked again, weeks or months or years later, and they’ve then said “Yes.”

It’s worked the other way around as well. I’ve said “No” to things that I then changed my mind about, and I’ve said “Yes” when my partner asked again.

And a good number of those times have resulted in some amazing sex — sex that both of us (or all of us) enjoyed tremendously, and would not have missed for the world.

But here’s the thing. The person who asked for something? The person who asked to be spanked, or to have their toes sucked, or to dress up like cowboys? They’re the one who’s more likely to be thinking about it. They’re the one who cares about it. If they’re the one who initiated it in the first place, they’re a lot more likely to initiate it again.

The person who said “No”? It may not occur to them to bring it up. They’re probably not the one who wants it or cares about it. If their partner never mentions it again, they might not even remember it.

So it doesn’t really make sense to insist that the person who said “No” is the one who’s responsible for putting it back on the table.

Example. If my partner asks me, “Can I apply hot peppers to your nether regions?” and I say “No, I don’t want to try that,” it’s probably not going to occur to me to bring it up again. Not because I’m traumatized by the very idea… but because it simply won’t be on my radar. Even if hot peppers aren’t an absolutely firm No for me — even if they’re something I’d be willing to try if my fears and reservations about it were allayed — once I’ve said “No,” for me the matter is going to be pretty much closed.

But that doesn’t make my partner a bad person for opening it up again.

At many points during my sex life, assorted partners have asked me, “Do you want to do X?”… even though I’d already said “No.” And I’m glad they did. If those partners hadn’t asked me, “Can we have anal sex? Can I cane you? Can we have regular vanilla sex without any kink or dominance play?” — despite my having said once upon a time, “No, I’m not interested in that” — my sex life would have been the poorer.

People change. A “No” today can turn into a “Yes” next week, or next month, or next year. In fact, sometimes the mere fact of having a sexual activity proposed, and having some time to think about it, can be enough to change a firm “No” to a softer “Let’s talk about this some more.” Sometimes all it takes to change our minds about a sex act is having it proposed by a caring partner who’s clearly not a maniac, and giving it some time and space to feel familiar and safe.

People change. People’s desires can change; people’s willingness to try things they think they’re not interested in (or that they’ve tried before and didn’t like) can change. And part of respecting our partners, and valuing our relationships with them, involves recognizing that people and relationships change — and being brave enough to revisit delicate questions, instead of letting things settle into inflexible cement where all questions are assumed to be resolved forever.

I’ve argued passionately that asking for what we want is part of being good, giving, and game: that one of the most important things we can give our partners is our willingness to be honest and vulnerable and brave about our desires. I don’t think I can say that… and then say, “But you can only do it once. Once you’ve asked, you have to put it back in the box, and never bring it out ever again.”

Of course it’s vitally important to respect people’s right to say “No.” But it’s also important to respect people’s right to ask for what they want. In fact, I’d argue that both these principles come from the same place — the basic respect for sexual autonomy.

There is, of course, a point at which “asking” becomes “pressure.” And I think it’s well worth having a conversation about where that line gets crossed. Especially since that line is going to be different in different situations, and for different people. To give just one obvious example: If your partner is young, and/or sexually inexperienced? That line should almost certainly be drawn in a much more careful, more conservative place than it would be with an older partner who’s had more sex. (Another reason why I think Scarleteen’s advice, while somewhat off-base as a general principle, is totally appropriate for this particular situation described in this particular letter.)

But I don’t think it makes sense to say, as Scarleteen suggests, that the ball should always be in the court of the person who said “No.” I don’t think it makes sense that the person who said “No” should always be the one to raise the question again.

Because chances are, they’re not going to.


So what does make sense?

How do we value the right to say “No” to any kind of sex we don’t want to engage in — while still valuing the right to ask for what we want? How do we draw the line between asking and pressuring? If we agree that “asking over and over again every single time you have sex” is a really crummy place to draw that line — but we also agree that “asking once and then never bringing it up again for the entire duration of the relationship” is almost as bad — then where do we draw it?

That’s the next column.


How Often Should You Ask For Something? Part 2: The Specifics

Draw the line
When it comes to asking for what we want in bed, how do we draw the line between asking and pressuring?

In my previous column, I wrote about a letter to Scarleteen, the sex advice Website for (primarily) teens and young adults. In this letter, a 17-year-old girl complained about her boyfriend who said he respected her sexual limits, but then kept asking for the same thing… over and over and over again. Scarleteen suggested that, since the boyfriend had made his desires clear, the ball was now in her court: his continued requests had crossed the line into pressuring, and he should bloody well knock it off.

Now, like I said last week, when it comes to the particular circumstances of this particular letter, this principle is very clear-cut. No matter what you might decide about the nuances and gray areas of “asking versus pressuring,” surely “asking for the same damn thing every single time you have sex with someone when they’ve clearly said ‘I’m not ready for this now and won’t be until at least (X)'” lands squarely on the “pressuring” end of that spectrum. Scarleteen’s advice on that front was entirely solid. If anything, I’d argue that they cut this guy too much slack. Personally, I’d be less inclined to advise his girlfriend to have a serious heart-to-heart about why he keeps bringing this up when she’s made her limits very clear… and more inclined to advise her, as Dan Savage so often does, to dump the motherfucker already.

Tennis ball
But like I also said last week: I don’t think it’s fair that the ball should always and forevermore be in the court of the person who said “No.” I don’t think it makes sense that the person who said “No” to a particular kind of sex should always be the one to raise the question again. If “asking for something over and over again every single time you have sex” is a lousy place to draw the line between “asking” and “pressuring,” I think “asking once and then never bringing it up again for the entire duration of the relationship” is a pretty bad place to draw it as well.

So where should we draw it?

How do we value the right to say “No” to any kind of sex we don’t want to engage in — while still valuing the right to ask for what we want?

How — specifically, practically — can we make this distinction?

I don’t want to play the Seinfeld game of coming up with hard numbers for broad relationship principles. (“If you’ve dated someone for three weeks, you can’t break up with them over the phone,” and so on.). But I’ve been thinking about this, and I’ve been coming up with a few very provisional guiding principles. (This is a rough draft, by the way, very much one of my “thinking out loud” pieces — so if you have problems with these principles, or can think of some I didn’t mention, please speak up in the comments!)

Power of persistence
1) Asking every single freaking time you have sex is right out. That’s the situation that sparked this whole conversation — so I want to get it out of the way right now. Again, I don’t want to get into a lot of strict Seinfeldian rules here… but I feel fairly comfortable with this one. If you want something so badly that you feel compelled to ask for it every single time you have sex with someone, maybe you ought to find a partner who actually wants to do that with you.

2) If your partner gives you a timetable for revisiting the question — respect it. If they say “No,” you can ask again now and then. But if they say “Not until I’m in college” or “Not until my divorce is final,” do not freaking well bring it up again until they’re in college or their divorce is final. (If that timetable isn’t okay with you, you’re entitled to get out of the relationship… but you’re not entitled to do it in a way that’s guilt-trippy or manipulative or otherwise douchey.)

3) Be more cautious and conservative when asking for something again with partners who are younger, and/or less sexually experienced. As a general rule, people who are younger and/or less sexually experienced often have a harder time saying “No.” (And alas, that’s often more true for young women than young men.) Learning that it’s okay to say “No” when your lover asks for something sexual takes a level of confidence that many young people, especially young women, haven’t learned yet. And there’s a big difference between people who’ve done lots of sexual exploration, people who’ve had time to map out both the broad and specific outlines of how they do and don’t like to boff… and people who are just mapping this stuff out for the first time. Taking those first baby steps can be daunting. It’s definitely not okay to nag people into taking any particular step before they’re ready.

Now, there is another factor making this principle somewhat tricky. And that’s that younger and/or less sexually experienced people aren’t just less likely to have the confidence to say “No.” They’re also less likely to have the confidence to initiate things, and to ask for things they’d like. Including things their partners have already brought up.

Example: When I was 17, I had a sex partner — a really great, fun, imaginative sex partner — who asked me if I wanted to be spanked. I said “No”: not because I didn’t want to, I desperately did, I’d been thinking about getting spanked for as long as I’d been thinking about sex… but because I was afraid of what wanting to get spanked would mean about me. But the moment I said “No,” I regretted it. I regretted it for the rest of that night; for every time we had sex after that; for years after this guy was out of my life. I was way too shy to bring it up with him again… and way too scared of having him think I was a pervert. But I would have been much obliged if he’d asked again. Probably not that night, but sometime.

When it comes to putting a sexual proposition back on the table, I do think it’s good to be more cautious and conservative with younger or less-experienced partners. And that’s true whether you’re older and more experienced, or a younger, less-experienced person yourself. But if it’s done in a way that isn’t noodging or guilt-tripping or otherwise obnoxious (more on that in a second), asking for something again doesn’t have to be pressure. It can be an invitation: an invitation to something your partner might want but doesn’t feel comfortable asking for.

4) When you ask for something again, make it explicitly clear that “No” is still an acceptable answer. There is a huge difference between, “So, can I spank you? Huh? Huh? I know you said ‘No’ before… but can I? Pleeeeeeeze? Oh, come on. Don’t be a wuss. All the cool kids are doing it. If you really loved me you’d do it”… and, “I know you said you didn’t want to be spanked, and if you still don’t that’s totally fine… but I’m still interested, and I just want to check in to see if your thoughts on that had changed.”

5) Talk about it when you’re not having sex. This is a good general principle of sexual negotiations… and it applies just as well to re-negotiations.

When people are in the middle of having sex, our thinking isn’t always at its clearest. To say the least. We’re vulnerable; we’re sensitive; we’re excited and horny. (Ideally, anyway.) Our judgment about whether we genuinely want to do something can be impaired. So if you’re going to bring up the “Have you changed your mind about (X)?” conversation, it’s much better to have it when you’re not already in the throes of passion.

6) Find out how firm the “No” is. Is this a traumatic emotional trigger? A profoundly nauseating gross-out? Or is it just a mild squick, something that might dissipate with time and information and familiarity? As I’ve written before: Is this broccoli or tofu?

If I’ve told a partner, “Eh, I’m really not into that,” it’s probably not going to bug me if they ask me about it again a month later. But if I’ve said, “Fuck no, not if it paid me a billion dollars and brought about peace in the Middle East” — it’s definitely going to bug me if they keep bringing it up. That doesn’t mean they should never ever mention it — I’ve had hard Nos turn into Maybes and even Hell Yes Please Oh Pleases in my life — but it does mean I don’t want to hear about it every month.

7) Start by asking if there’s something your partner wants. The “Have you changed your mind about (X)?” conversation is likely to go better if you don’t make that the opener. Things are likely to go better if the conversation starts with, “Is there anything you’d like to do sexually that we’re not doing?” This makes it clear that you care about your partner’s desires. It sets up your re-negotiations, not as a nagging demand, but as part of an ongoing conversation about sex, a two-way street intended to get everyone where they want to go. It’s considerate and thoughtful. (And from a purely selfish, Machiavellian standpoint, it’s good strategy.)

8) Tit for tat. And speaking of good strategy: If you’re asking your partner for something they’ve said “No” to? A good approach can be to let them do it to you first. If you want to spank them, to tie them up, to fuck them in the ass, and they’re not interested — offer to take it before you give it.

This doesn’t work in all situations or for all sex acts, obviously. “I’ll let you fuck me in the bathroom of Madison Square Garden if you’ll let me do the same with you” is clearly not a fair trade. But for some kinds of sex — sex where there’s some inherent inequality or imbalance, for instance — this can be a way to allay people’s fears, and make it seem safe.

9) When someone says “No,” it’s okay to ask “Why?”

We have to be very, very careful with this one. That “Why?” can’t be guilt-trippy. It can’t carry any implications that there’s something bad or wrong about saying “No” to a particular kind of sex. Not even a little.

But sometimes, when people say “No” to a certain kind of sex, it’s because they have misconceptions about it. (I said “No” to anal sex for years because I was under the misconception that it always hurt.) And sometimes, even when people have entirely valid, non-misconception-y reservations about a particular kind of sex… those reservations can sometimes be addressed. (“We’ll go slow, and we’ll use lots of lube, and we’ll slow down or stop if it starts to hurt” leaps to mind.)

Again, we have to be seriously careful with this. There’s a difference between saying, “Why are you such an unloving, uptight prude that you don’t you want to give me this thing I want so much?”, and saying, “I accept your No and will respect it — but I’d like to know where that No is coming from, since some people have misconceptions about X, and there might be some way we could do it that would address your concerns about it.”

But if it’s done in a non-judgmental way, asking “What are your reasons for not wanting this?” can be a good start to settling sexual differences and arriving at compromises that everyone’s happy with. And it can lead to better overall understanding of each other’s erotic maps… and to good conversations about other things you might or might not want to do.

Nobody is required to give an answer to the question, “Why don’t you want to do that?” The answer, “Oh, I don’t know, I just don’t feel like it” is perfectly valid. But it’s a valid and reasonable question to ask. And I think it’s valid and reasonable to ask your partner to at least think about the answer.


That’s my rough draft.

Wanna help me fine-tune it?

How Often Should You Ask For Something? Parts 1 and 2
The Bolingbrook Babbler:  The unbelievable truth is now at

5 thoughts on “How Often Should You Ask For Something? Parts 1 and 2

  1. Jan

    For me the whole two pieces were common sense nailed.
    I read and tried to take my mind back to being a teenager and saw the points better that way.
    The whole pressure thing, either from the partner, or peer pressure can make teens go further than they really want and have regrets. Or just a bad experience which puts them off things for years.
    The talking about stuff while not having sex is spot on! It can open the mind to thinking about things rather than shutting minds off forever!

  2. 2

    I would add a corollary of “don’t get into relationships you can’t easily get out of without making sure you are and can stay satisfied in them” and a subcorollary of “do not automatically take a partner’s word for it about how easy it would be to get out of a relationship.” :/

  3. 3

    Yeah this advice would have been great when I was a teenager…It also would have been great advice for my boyfriends back then. Oh such sad misconceptions 🙁

  4. 4

    As a refinement of #9, if your partner says no, and you ask why not, at least make some effort to explain why you want the activity. There’s a world of difference between “Let’s try anal because it makes spooning that much better.” and “Can I fuck your ass while secretly have a rape fantasy?”

  5. 5

    “As a general rule, people who are younger and/or less sexually experienced often have a harder time saying ‘No.’ (And alas, that’s often more true for young women than young men.)”
    I think the genderedness of the difficulty is going to depend on the act being asked for. I think most guys actually have a great deal of difficulty saying no to sexy-times in general, and to vaginal intercourse specifically, because guy’s are expected to want that. They lose a lot of masculine cred if they reject such advances, and are far more at risk of being seen as not being attracted to or not wanting their partner. I think partners of males (in the case of het relationships, women) need to be a lot more careful with that than they think.
    But for less mainstream/vanilla activities, yes, I think women typically have a harder time saying no.

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