How to Do It

I’m Racked With Guilt Over a Sexual Encounter From Years Ago

Should I reach out to my partner to process, or just let it go?

Guilty looking man holding a pair of glasses next to a neon pink condom.
Photo illustration by Slate. Photo by innovatedcaptures/iStock/Getty Images Plus.

How to Do It is Slate’s sex advice column. 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 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.

Advertisement
Advertisement
Advertisement

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?

Advertisement
Advertisement

—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.

Advertisement

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.

Advertisement
Advertisement
Advertisement

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.

Dear How to Do It,

Advertisement

My girlfriend and I have been on a steady upward trend of “athleticism” in the bedroom, and it’s amazing. But now she’s got a torn ligament in her knee (not because of the sex). What are some ways in which we can keep the game alive and not both sit on the sidelines?

—Injured Reserve

Dear Injured,

What do athletes do when they tear a ligament? They sit it out until it’s better. Put your rigor on ice for a bit and follow the doctor’s guidelines as they pertain to sex. At the very least, some kind of oral and manual should be doable, as may be some modified missionary (perhaps at the end of a bed so that her injured leg is fully off and out of the way). Go easy now so that you can speed up your complete return to the arena, champ.

Advertisement

Help us keep giving the advice you crave every week. Sign up for Slate Plus now.

Dear How to Do It,

I’m a 31-year-old straight, cis man that has been in a monogamous relationship for the last 12 years. We get along perfectly in almost every way. Almost: Our sex life leaves a lot to be desired. My libido is way higher than hers, but I’ve learned to live with that as best I can. My biggest hang-up is how boring and one-dimensional the sex we do have actually is. My wife seems to be afraid of trying anything new, and sometimes, I’m not convinced she even likes sex at all. Every time we’ve tried something (at my request or suggestion) it inevitably ends with her being disgusted or uncomfortable and me feeling ashamed and confused.

For example, she did not like giving or receiving oral the one time we attempted both. Changing to any position besides the three or so we default to is usually met with her saying it feels weird and asking we switch back to something she knows. Fingering and vibrators were a part of our early experimentation, but now if I linger too long on paying attention to her, she asks if I’m “ready to start yet.” She only seems to want me to come so that it can be over. I’ve tried asking her many, many times what she wants in bed, and I either get a nervous shrug or she says something like “I like when we go really fast.”

Advertisement

I hit my breaking point recently when she very unenthusiastically agreed to try something new the last time we had sex. Immediately afterward, she described the experience as gross and got in the shower (she never ever showers at night or after sex). I felt so humiliated and ashamed I couldn’t even look at her after she came back to bed. She doesn’t seem too upset about that night, but I keep reimagining her revulsion, and it’s making me feel like never wanting to have sex again. I would love to do anything she wants to try, but she hasn’t asked or hinted for anything relating to sex in the last decade of our relationship. Am I pushing too much in wanting to try different things?

Advertisement
Advertisement

—Ashamed

Dear Ashamed,

You’ve gone too far in that you don’t seem to be getting anywhere. There’s nothing wrong with talking about your desires with your partner, and it’s only natural to ask if they’re interested in partaking, especially when you’re in a monogamous arrangement. By your account, your wife did consent to the sex acts that ended up disgusting her, and you suggest that it doesn’t seem to have affected her (though I wonder if her not seeming “too upset” means she is somewhat upset). However, enough of these incidents have occurred to establish a pattern in your partner, and it would not be prudent to continue your attempts at bedroom innovation. She’s sending you signals, loud and clear—so loud and so clear that they’re affecting you. I do not think that there is anything inherently shameful in what you’ve described, but you are both upset as a result of something that ideally would be making you feel good. Like Marvin Gaye said, we’re all sensitive people.

Advertisement

You’ve tried asking her what she wants in bed, but I think you have a more rudimentary excavation to attend to. What’s going on with her? What changed? What’s prompting these reactions? Tend to the foundation before you start changing the ornaments. Her current attitude about sex could be a result of any number of things, including unacknowledged asexuality or trauma that she hasn’t informed you about. That’s why it’s really important to refrain from accusing or even voicing frustration. Patience will serve you well here. You’re both clearly affected by this, and it’s time to start unpacking why. Ask her what’s up. Tell her you’re confused. Frame your experience emotionally and with optimism that this issue is solvable. If she won’t budge and nothing changes, your relationship is likely to remain as you’ve described, and you’ll have to consider how long you want to sit in this breaking point.

Advertisement
Advertisement
Advertisement

Did you write this or another letter we answered? Tell us what happened at howtodoit@slate.com.

Dear How to Do It,

I’m happily married, 14 years, four kids, and a strong, great relationship. My husband often brings up the fantasy of me being with another male lover. I understand his desire and don’t judge it. I enjoy how much it turns him on. We’ve had some sexual adventures (we’re certainly not prudes), and even enjoyed (pre-COVID) some safe group sex. It’s always been together in the same room. I’m picky and careful. An opportunity has presented itself with a guy I’m genuinely attracted to. We’ve had honest discussion about it. I’m pretty certain the guy would be into it. My husband clearly is! He assures me he wants this. I’m having trouble, though, with the idea of doing this without him. It’s one of those things that has potential unintended consequences! Is this crazy to follow through with?

Advertisement
Advertisement

—Nervous Wife!

Dear N.W.,

It would be unwise to have sex with this guy only because your husband wants you to. It’s kind of you to want to do this for him, but your misgivings may be signaling your prevailing lack of interest (despite whatever abstract attraction you might feel to this third party). It’s hard for me to say, not being inside your mind. I do think it’s wise to think about and discuss the unintended consequences, though at this point, you’ve had an opportunity to see how nonmonogamous sex affects you and your relationship. Seems like it hasn’t! I think you should ask yourself who wants this sex between you and this guy more: you or your husband? If the answer is anything but a trumpet-clear “Me!,” I’d say avoid.

Advertisement

— Rich

More How to Do It

I am a year and a half into being a widow, and nine months into a new relationship. That may seem offensive to some, but I ask that you stick with me without that judgment. My husband and I had had an intense BDSM relationship where I was the submissive. He died suddenly. Every single time I try to take the lead now (especially where I am on top), I cannot stop thinking about my late husband. It totally shuts me down. But I am not in a BDSM relationship now, and I have not always been submissive. I want to take the lead with my new partner. Where do I even start working through this?

Advertisement