Our advice columnists have heard it all over the years. We dove into the How to Do It archives to share a selection of classic letters with our readers. Have a question? Send it to Stoya and Rich here. It’s anonymous!
Dear How to Do It,
I am a queer woman in my early 30s who is in a relationship with a straight man. We’ve been together for about a year and have a great sexual connection. Part of what makes our sex life so great is that we’re open with one another about our attractions not only to each other, but to other people. In the past, particularly at the beginning of our relationship, I found it thrilling when he described his desire for, say, a particularly sexy waitress. This generally turned into something exciting that stimulated our own intimacy. We’ve each also been open with each other about watching porn (and have even watched it together), and I know he particularly likes watching cam shows. For context, this is something we’ve discussed on a nearly daily basis. I felt, and feel, grateful to have found a partner whose sexuality is seemingly so compatible with mine and with whom I can be open about the many manifestations of my desire. But lately I’ve been having trouble enjoying this aspect of our relationship. I just went through a few months of incredible stress at work that left me feeling exhausted and insecure. The past few times he’s mentioned finding someone sexually alluring, it stung in a completely unexpected way. Last night, via phone, he mentioned that he was watching a great cam show at the moment, and I had to choke back tears.
I felt hurt because earlier in our call I’d described feeling lonely. (I am traveling for the next month for work, so we are apart physically.) I wish he’d been able to understand that it wasn’t the right time for that. I tried to express to him that this time, hearing this didn’t feel good for me. He dismissed this by saying, “Oh, come on, you love it.” I left our call feeling insecure and inadequate. At the same time, I understand why this might be hard to spot as a boundary for him, because it’s been so much a part our sexual communication in the past. How do I express my boundaries, without attaching stigma to his (or my) sexuality and without stripping the fun out of our sex life? I don’t want to be a total wet blanket, but I need to set some boundaries so I don’t keep feeling hurt!
Dear Just Us,
I’m sorry you’re having a tough time at work. It’s completely normal for your sexual desires to be affected by other areas of your life. It makes sense that insecurity in one area could cause difficulty relaxing and feeling comfortable in the sexual realm.
I really don’t like that your boyfriend responded to your issue with dismissal. I want to give him the benefit of the doubt, and I think you do as well. A phone call, as you’ve learned, can be a difficult medium to have emotional dissuasions over. Phone is generally still better than text message, but it can be easy to misread a situation without access to that extra layer of information that comes from facial expressions and body language.
So, hoping that he was just swept up in his arousal or otherwise preoccupied, I think you should try talking to him again. Pick a time when neither of you has a pressing appointment and it’s still early enough for both of you to be awake and clearheaded. Think about the space you’ll be talking in—is it a controlled environment and free of distractions? Then, in your own words, say something along the lines of “Hey, this game we play that we both really love and get off on—I’m having a problem at work that is so big that it’s undermining my ability to enjoy our game.” Let him know that you’re having a hard time and that there’s some collateral damage in the sex zone. Tell him that his dismissal of your feelings hurt. You aren’t doing either of you any favors by hiding your emotions.
Then tell him what you do need. Something like “I need us to focus on each other for a while—probably until I recover from this work thing, and I’m not sure when it’ll be resolved, much less when I’ll be feeling back to normal. No matter how much I want to be fully open right now, I’m just not there at the moment.” Be as clear as possible. Boundaries have to be defended sometimes, so you might need to revisit this subject a couple of times. If he seems like he just isn’t listening after two or three serious conversations, you might be looking at a red flag.
From: “I Just Jumped on Dating Apps and I’m VERY Excited for Sex” (June 18, 2019)
Dear How to Do It,
My wife and I are in our late 40s/early 50s, and we’ve been together for almost 12 years. I’m more of a homebody by nature, but I do love to travel when the bug hits (which tends to be in spurts). She’s more my opposite in that regard as she loves to travel all the time; sitting at home too long gets her antsy. So in that respect, our personalities balance each other pretty well. As we’ve grown in our relationship, so has our sex life, and I feel (and she’d agree) that it’s better now than it was when we were dating (and it was really good then). To put it plainly, it’s freaking awesome, and I have no issues whatsoever; the frequency (four-to-five times a week), the communication, and the penchant for experimentation/exploration is all great. Unlike many articles I’ve read about the pandemic having a sobering or debilitating affect on many couple’s sex life, it’s actually been pretty good for ours. And there’s the problem.
Before all of the lockdowns, we went out, traveled, did “normal stuff that couples do.” Since the pandemic started, we’ve had to become pretty creative in coming up with ways of entertaining ourselves to stave off boredom being cooped up. My homebody side loves it (I do miss the travel/hotel sex though) and for her part, she’s done OK with it as well. And I believe that in forcing us to be so creative, it’s really helped enhance and kick our sex life into another gear. My problem, or rather my fear, is—what now?
When the virus has been brought under some semblance of control and life can go back to some sort of normalcy, what happens to all of this great sex? I don’t want what we’re experiencing NOW sexually to wain or waver in ANY capacity. But the doors are going to open eventually and we’re going to be able to roam around as we once did. Two things can’t occupy the same space, so when we’re able to get out more, something has to decrease, right?
So I guess my question is what can we do to maintain where we are now sexually while picking back up those things that we enjoyed before the lockdowns? If I sound like a “horn dog” then I am; my libido has gotten stronger over the last year and I’m immensely grateful since it could very well be going the other way. I don’t think we’re anywhere near our sexual peak and I’m REALLY enjoying where we are. And for her part, she’s expressed the same. So how can we maintain and even build on this same level of “peak freakiness” once staying home is no longer the primary option?
—Not Liking but Liking the Lockdown?
Life is full of ups and downs. Usually one or more simultaneously, like COVID and your increased intimacy. Sexual desire, like energy, ebbs and flows.
I think your best bet is to enjoy the current moment as fully as possible. When your thoughts turn to possible decreases in desire, purposefully refocus on the bounty you’re currently experiencing. Save up those memories for the future, and relish in them to the utmost of your ability now.
And who knows—maybe you’ll find you’ve missed those other activities once they’re feasible again.
From: “I’ve Had a Wild Sex Life During the Pandemic—and I Don’t Want It to End” (December 16, 2020)
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Dear How to Do It,
I’ve been married for about 10 years. About a year ago, I had a brief affair. We realized it was a mistake and ended the relationship. He lives far away, so I haven’t seen him since. Neither of us told our spouses about it, and we have no intention to. I’ve never done anything like that before, and I won’t ever again. I feel bad about it and wish it hadn’t happened, except in one respect: The sex I had with this man was off-the-charts amazing. Like, I didn’t realize that sex could be like that. Sex with my husband is fine—but I feel like I’ve been watching a black-and-white TV my whole life and I suddenly discovered Technicolor exists. I don’t want to go back to this ex, but I can’t stop thinking about the sex. I realized that I get very turned on by things that are out of my husband’s comfort zone. I can’t talk to my husband about it—telling him about the affair would only hurt him, and when this kind of topic has come up in the past, he has been very clear that if anything ever happened, he wouldn’t want to know. How can I get over this?
—In Living Color
Dear In Living Color,
Are you sure you can’t talk to your husband about it? Really, really sure? I know you say he would never want to know, but I ask because I’ve encountered many people who thought they couldn’t talk to their spouse about major problems and turned out to be wrong. At least one person I know almost destroyed a decade-plus-long marriage because he was afraid of being honest with his partner. The whole thing was sad.
Maybe you really can’t talk to your husband, though. Maybe he really doesn’t want to know. If that’s the case, you’ll have to live with the burden of knowing the grass is greener on someone else’s groin. You’ll have to hide your secret. But I don’t think you have to suffer in silence, wondering if you could be that sexually satisfied with your husband if only the two of you could connect, honestly and openly. Why not at least talk to your husband about trying something new in bed? Maybe his comfort zone can expand; maybe he’d be excited to explore with you. Write down a list of the reasons you don’t think you can talk to him. Ask yourself if those reasons are real or fear-based. Really consider this. Please.
The good news is that part of the appeal with this man you had the affair with could have been the transgressive nature of the act. Another part of the appeal was probably the novelty. It’s not like this guy had a magic penis or something super rare that you’ll never find again. You ended the affair, so focus now on fixing whatever led you to it in the first place.
From: “An Affair to Remember” (June 11, 2019)
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Dear How to Do It,
My friends and I are close and very candid about our sexual experiences. I generally don’t have sex with my friends, but they don’t believe in those restrictions. We were talking recently about planning a weekend where a group of us would go away and possibly have an orgy amongst us. I’m really excited about the idea, except for the fact that I have a never-before-admitted crush on one of my best friends, Q. I liked him before we became close friends, and once we became tight, I suppressed it for the sake of our friendship. He’s had girlfriends and hookups over the years that bothered me a bit (including a hookup with one of our friends), but I never said anything because no one knew that I had feelings for him. Now the group is planning this trip, and I feel like my only two options are to back out of the trip without saying why, or fully participate in the group sex with the possibility that it’ll complicate my friendship and feelings for him down the road. I never planned on saying anything to him because I believed in the boundaries of our friendship, and I worry that being honest about how I feel will blow up our friendship because he’s very dear to me. Am I really stuck here? Is there another option I’m not seeing?
Dear Orgy Issues,
Let’s talk about Q first. There’s a big difference between approaching a friend and gently expressing that you have romantic feelings toward them in addition to the feelings of camaraderie and friendship that they already know about, and, say, throwing your mouth at their mouth sans warning with the vigor of a small puppy.
Spend some time thinking about your feelings for Q. What would you want with him if he’s interested? Occasional hookups in addition to your friendship? A long-term relationship with major commitments headed toward marriage and mutual child rearing? What are you content with if he isn’t interested in anything romantic or sexual with you? Are you happy to put your desires aside for as long as the friendship lasts? Are you comfortable never speaking of it again, or would you want to check in again in a few years? Get it all sorted in your head to the best of your ability, and then consider doing the big scary thing before this weekend arrives.
It’s possible Q already knows you have feelings for him. We’re rarely as good at hiding these things as we’d like to think. It’s also possible that he’s been crushing on you while staying completely in the dark about your feelings. I mean, he’s planning to attend an orgy that includes you. Yes, it is also possible that he’ll panic and throw years of close friendship away. I think that’s a minuscule chance, though. And I think that clearing the air and expressing yourself—and the potential rewards from doing so—are worth that small risk. Think about how you’ll respond to various reactions Q might have, and if there’s even a hint of “No,” be prepared to hear, receive, and respect that.
Now let’s talk about the orgy. You don’t have to fully participate. Or, rather, full participation can mean anything from playing the role of Condom and Paper Towel Distributor to being the star of a sex pile involving everyone in the room. You, and every other participant, have the right—responsibility, even—to act according to your desires and comfort zones. You have so many options. You can be a voyeur, contributing by providing a gaze for the exhibitionists to perform for. You can focus totally on kissing. You can hook up with some people and not others. You can have penetrative sex with every single attendee who is interested. It might be a good exercise to try to make an exhaustive list of all the ways you could participate in an orgy and take note of the ones that feel appealing.
Best of luck, and remember to brush up on your safer sex practices in the coming weeks.
From: “My Friends Want to Have a Big Orgy Weekend Together” (Feb 12, 2020)
More How to Do It
I have been with my boyfriend for about two years. He is 37, and l am 49 (I divorced four years ago). I am so into this guy and enjoy our time together every day—he always makes me smile and makes me laugh most days. I feel very secure and happy with him when we’re together. He is extremely good looking and has a smile and eyes that can light up a room, along with a very athletic strong body. He’s very intelligent, street smart, a good provider, and takes me nice places all the time. We never have sex, but he will orally stimulate me and is so good at that. It’s amazing sometimes. It has taken me a while to figure out that he is gay.