Our advice columnists have heard it all over the years—so we’re diving into the How to Do It archives to share classic letters with our readers. Have a question? Send it to Stoya and Rich here. It’s anonymous!
Dear How to Do It,
About 15 years ago when I was in my early 20s, I dated a woman who I’d known previously as an acquaintance. We were never that serious, but we did have sex multiple times over the course of a few months. Looking back on this, I am mostly embarrassed by my lack of ability to be a decent sexual partner. I was pretty inexperienced sexually (it was maybe my fourth sexual experience) and a little terrified. During one of our sexual encounters, we had sex once, and I came with a condom on. I came way faster than I wanted to, and she wasn’t close to coming herself. So we started again, however this time, I made a mistake.
I came without a condom. In my memory, I assured her it’ll be fine, “I already came once. I’ll be good now.” It was not fine: I had the urge to come again within a few minutes, she seemed closer so I didn’t want to stop, and I ended up coming inside of her without a condom. She still did not come, and I just lay down and we fell asleep.
We never discussed the fact that I came in her, and if I’m being honest, I don’t exactly remember word-for-word what was said and not said about me using a condom. In my memory, we briefly discussed my not using a condom, but maybe that’s just the story I tell myself now. Maybe we just started up again without any real conversation. We never had sex again, though we would occasionally see each other out and about.
Now, years later, I feel like she deserves an apology from me. Did I violate her trust? Was there clear consent? Well, clearly the consent wasn’t clear and maybe it wasn’t there at all. I really don’t know or remember, but the guilt deep in my stomach tells me that the answer is maybe that it wasn’t. We’re still friends on social media, and I have this urge to write her and apologize. Is this worth doing? Would this just be me processing my own guilt? We are both long-married with children. How do I move forward with this potential wrongdoing from my past?
—Fog of Guilt
Dear F.G.,
Your shame and guilt are so palpable and your status as an unreliable narrator so pronounced that I wonder if there is bigger-picture mental health stuff going on here. Sometimes false memories present as symptoms of OCD, and your letter reads like you’re in a cycle of rumination. I mean, the stress that this is causing you some 15 years later is stressing me out, and we just met.
I don’t think it’s wise to reach out to this person with whom you had a fleeting dalliance in the mid-aughts—not until you’ve talked to a professional and have a better handle on what might be going on with you.
In the meantime, give yourself a break over something that may or may not have happened 15 years ago. That’s all I think you should do about it for now. This is your problem to solve for yourself. It’s bad enough that it may have happened; if she wasn’t aware, how much good could you do by bringing it to her attention? Unless she had a child approximately nine months after you came inside her, I don’t see this information as being particularly useful. Out of the blue, you message her with information that makes her feel bad and angry and that she can do absolutely nothing about? That’s textbook bothering. At this point, it’s reasonable (kind, even) to assume that if she wanted to discuss this with you for the sake of closure, she would have. She knows where to reach you.
At most (and I’m not really recommending this), you could strike up a conversation via social media to ask how she’s doing. You can mention that you have felt awkward about things and want to make sure you’re all good. Keep things vague, and in service of allowing her to say her piece, just in case she doesn’t feel so empowered. But tread lightly and forgive yourself. Don’t come in someone again without notifying them (unless they’ve explicitly given you a pass to do so in advance), and come to peace with the idea that you didn’t intend to hurt anyone since you didn’t intend to do it at all.
—Rich Juzwiak
From: I’m Racked With Guilt Over a Sexual Encounter From Years Ago. (Jan. 11, 2021).
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Dear How to Do It,
I’m a gay man in my late twenties and a tattoo artist. I’m doing an extensive piece on a gorgeous man I know well and have a huge crush on. He is single and is at least bi. There is definitely chemistry between us. Whenever we get together, we just talk and talk. Twice, he has mentioned considering a more serious relationship now that he’s graduated, and I think it might be a hint.
The piece I’m doing for him needs a lot of shading, which really hurts, especially over the ribs. He dealt with it OK, but his suffering really got me going. I was rock hard and lucky that my apron concealed this. Later on, it felt wrong and disgusting to have felt that way. I’ve never been turned on by tattooing someone before and always try to be professional and respectful. Getting off on his pain seems unprofessional and almost like a breach of trust. I’m a compassionate person, and I’ve never considered myself a sadist.
This piece is going to take at least two more sessions to complete. I get turned on thinking about it, but that doesn’t feel right. I can’t get another artist to do it because I have a unique art style. I was planning to make a move on him (outside of work) once the piece is done, so that on the off chance he says no it wouldn’t be so awkward, but now I’m feeling uncertain about everything. How good of a match could we be if I’m getting off on his suffering?
—Maybe Sadist
Dear Maybe Sadist,
This would be a bigger issue if you weren’t already attracted to him, and even then, it would only be an issue if he weren’t into masochism. For all you know, he is, and you’re a perfect match.
If you previously haven’t considered yourself naturally kinky, you may have encountered your awakening, which is a good thing. Conversely, there is more to tattooing than just pain, as you are well aware. There’s the closeness, the penetration, the adding to someone’s life—all of these could be informing your boner as well. You won’t know until you pursue it. I say go forth as planned with making your move after the work is complete, and be prepared to put a pin in the whole I-want-to-see-you-suffer thing for now. See if you can nurture the spark without that component. If you can’t, see if he’s into it. You’ll never know if you don’t try, and you may regret it if you let this opportunity pass.
—R. J.
From: I’m Getting Turned on at Work, and the Reason Why Is Really Freaking Me Out. (Dec. 18, 2022).
Dear How to Do It,
Two of my friends are dating, and I keep having super-hot sex dreams about them. Now, nothing else compares.
These two friends (male and female) began dating about a month after I (female) met them, so essentially for our whole friendship they’ve been dating. The problem is, I was attracted to both of them before they started dating, and now that they’re together, it’s worse. I just can’t seem to get rid of my feelings for them. It’s like I used to have a crush on each of them separately, and now I have a crush on them as a couple. To top things off, I can’t stop having dreams in which my wildest fantasies with them come true. The dreams are really good, so good that now I find myself disappointed by sex with other people. Even masturbation doesn’t do it for me, every time I try to get off I can’t help but wish I were with them, and anything else is subpar. I also really value my friendship with them and I don’t want to ruin things. Help!
—Three’s a Crowd
Dear Three’s a Crowd,
You can’t have everything you want, and in fact, the intensity of your longing has no bearing on your entitlement. Your yearning for what you don’t (and may never) have, moreover, should not get in the way of appreciating what you do have: hot friends. That alone is an aesthetic reward. You should also cherish your dreams—André Breton wrote at length in attempt to correct what he saw as a mass underrating of dreams in his first Manifesto of Surrealism. (From an English translation: “I have always been amazed at the way an ordinary observer lends so much more credence and attaches so much more importance to waking events than to those occurring in dreams.”) If you can’t have these people, at least you can dream about them regularly. As consolation prizes go, at least that one is vivid.
If I were you, I’d wait for someone hot to come along and distract you. It will happen. You will not spend the rest of your life pining for these people. If this longing is so unbearable, propose a threesome. It could ruin things, yeah, but if you’re living in a state of distraction, blowing things up may be good for you, anyway.
—R. J.
From: I’m Having a Very Distracting Reaction to My Hot Friends’ New Relationship. (Aug. 07, 2022).
More Sex Advice From Slate
My partner is a pretty serious sub. I am happy to take the lead in sex but being “dominating” doesn’t come that naturally to me. They want me to be rougher in bed and even have some pretty good suggestions for what to do and say. The thing is, when I’m having sex, all I’m really thinking about is how much I love them, so I end up saying things like “you’re amazing,” realizing that I was supposed to be trying to call them demeaning names, and following it up with “…an amazing whore!” I feel laughable. What do I do?