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,
I’m a 34-year-old guy who was married for 10 years to a woman I loved very much. She was my high school sweetheart before she was my wife. We had three kids together, and we were very happy. She was killed by a drunk driver four years ago, and I was absolutely devastated and became deeply depressed.
I don’t know what I would have done if not for my friend, “Jack,” stepping up. He has long been probably my best friend. He’s always been a fun “uncle” to our kids, and gets a kick out of spoiling them. He’s spent a lot of time with our family, and is someone I would trust with anything. He would listen when I was upset or pissed or whatever as I was grieving my wife, supported me more than anyone through the awfulness of the legal process to determine what happened to the guy who killed her, and I can’t imagine what I would have done without his day-to-day help with everyday stuff. He helped me transport the kids around to their various activities, fixed a major issue with our house (he’s an electrician who runs his own contracting business) refusing to take anything in return, and has just been a huge emotional support. I feel intense gratitude for everything he’s done for us, and he’s helped me be in a much better place than I was four years ago.
I have realized I think I am developing sexual/romantic feelings for Jack now though, and it has thrown me for a loop. I feel intensely close to him after all his support, he’s so great with my kids, and he’s just such a good guy. Since the COVID-19 pandemic started, he’s been basically living with us to give me a break at times since I’m working from home while trying to do online school for all three of my kids. It’s been such a relief to have him around I can’t even express. I literally don’t see how I could be keeping everything together without him. All of my kids have expressed in various ways that they like “Uncle” Jack living with us. It all feels increasingly domestic, and I feel happier than I’ve been in ages. I find myself feeling intensely jealous and resentful of any hypothetical partner of Jack’s, and increasingly thinking of him as my partner rather than “just” my live-in friend. I think I would be devastated if he got together with someone at this point.
I’d never been attracted to a guy before, so all this has really surprised me. I’ve been unsettled to find myself noticing physical things about Jack, and actively thinking about what it would be like having sex with him. I feel like I am hyper-aware of him in a way that I have only ever felt with girls/women before. The other day I caught myself staring at his hands getting turned on thinking about him touching me. A few times now I’ve also had sexually explicit dreams about Jack. It freaks me out a little because I don’t fully understand what has flipped this switch in my brain. I know Jack has had some experiences with men before (he identifies as “straight but open-minded”), but that he prefers women for relationships, and so maybe he wouldn’t be interested anyway. It’s been pretty clear he cares for me a lot though based on his actions these past few years (he has outright told me he loves me and my kids in way that implies he thinks it should be obvious), he has said things that would plainly imply he thinks I’m good-looking guy, but I really can’t tell if there is anything on Jack’s side besides just deep platonic feelings.
I really don’t know who to talk to about this, as my family is quite conservative evangelical, and I don’t want to talk to a mutual friend (most of my close friends are also friends of Jack). I know my family will flip out and think Jack somehow seduced me into feeling this way. My parents have never liked Jack because they see him as being way too liberal (they are strongly right-wing), he’s gone to BLM protests (my parents are kind of racist), and he’s never settled down in a traditional way (wife, kids, etc). I think Jack drives them kind of crazy because they feel like he should be one of them (he grew up in the rural Deep South like my mom did, he’s a veteran from the same branch my dad served in, etc.), but he’s kind of their polar opposite. Honestly, my parents have been pretty unhappy even about Jack living with me, and have told me repeatedly he’s a “bad role model” for my kids. I have moved pretty far myself from the views I was raised with. Even still, I’m not sure I’m ready to pursue a relationship that has the potential to blow up the most important friendship in my life, will probably make my parents stage an intervention to save me from this “lifestyle,” and may lead to a serious rift between my kids and their grandparents.
I’ve been realizing that Jack just makes me really happy though, and that it makes my kids really happy having him around, and so maybe I should just go for it. I don’t think it would end our friendship for me to talk to Jack about how I feel even if he’s not interested in being more, though I would be pretty down if it fundamentally changed the way he was with me/how close we are, which is a risk, I suppose. I never expected to be having a crisis of sexuality in my mid-30s, and I guess I’m wondering if this actually happens to people? Going through life thinking you’re 100 percent one way, sexually, then realizing maybe there’s that one person who’s the exception? I can honestly say I’ve never had these sorts of feelings towards any other guy before, so do you think I should be more distrustful of what’s motivating them, and their authenticity? I feel like my family is surely going to try to convince me I don’t know my own damn mind if I pursue things with Jack, so I guess I am partly looking for some reassurance that I’m not crazy to take this long to realize I’m maybe a little gay, I guess?
—A Little Gay
Dear A Little Gay,
After all that, I’m swooning, and there is no way on God’s gay Earth that I’m going to dissuade you from pursuing romance with Jack. Duh. You love him, he loves you, and the risk of derailing your friendship by declaring your love is minimal, by your own estimation. If we think about your life as a garden, what you should cultivate (love) and weed out (that which may obstruct love) is clear. Unfortunately for you, that which may obstruct love is your bigoted parents, but fortunately for you, you are a grown man who is not dependent on them in any way that will interfere with your immediate well-being. And furthermore, you’re too old to let your parents dictate your life. I understand their enduring relationship with your children is a concern, and your consideration on this matter speaks highly to your character, but they would ultimately be punishing themselves to hold your decisions against your children. They could also have a change of heart upon learning that their son is in a relationship with another man. Sometimes lived experience melts away abstract bigotry. You know them better than I do, obviously, but it happens.
All of that seems clear-cut to me. Less obvious is the internal mechanism that has led to this previously unthinkable condition of you perhaps (read: obviously) being in love with another dude. The how of sexuality formation is something we may never completely understand. There are so many variables, so many inextricable factors (nature, for example, is never not nurtured—all biology exists in an environment), so much range within our species. It makes sense that a spectrum ensues. It’s probably more useful to think about your experience not as a switch being flipped by a gradual process that led you to where you are now. It won’t hurt you to ponder whether Jack is the one guy in 7 billion that you were capable of loving and it took you some years to realize it or if something about your closeness allowed that love to happen (keep a journal, write it out, show your work), but what seems true regardless is that you were open enough to allow yourself to feel this love. That level of openness is what I call living right. I think you should trust these feelings as you do your other feelings: Your predispositions and experiences have all led you to where you are right now, and it seems arbitrary to label some as real and others as not. Maybe if your wife’s death were more recent, I’d urge you to tread more lightly so as not to jump into something for the sake of distraction, but it seems like you have a great handle on your situation and have had plenty of time to mourn her death.
Do people realize things about their sexuality as they mature? I sure as hell hope so. And I hope they keep realizing them. There is certainly documentation of people who previously thought themselves to be straight and then realized they weren’t: About 10 years ago, “later-life lesbians” had their moment in the media sun, following the publication of psychologist Lisa Diamond’s Sexual Fluidity: Understanding Women’s Love and Desire. Less attention and reporting focused on men who understand their sexual fluidity later than what’s typical, but there’s information out there (here’s a recent thread on the subreddit AskGaybrosOver30 that you may find relatable). But even if this weren’t a reported phenomenon, would it make your feelings for this guy any less real? Nope. It wouldn’t. You are who you are, and who you are is someone who caught feelings for a guy you pseudonymously referred to in a letter to an advice column as “Jack.” You know exactly that you need to do, and I couldn’t be happier to tell you to go do it.
Did you write this letter? Follow up with us please!
Dear How to Do It,
My daughter is 16 and has a serious boyfriend. We aren’t against premarital sex, but I would rather my daughter wait until she has a little bit more life experience to be able to gauge whether she is ready to have sex. That said, we’ve given her the safe sex talk. I think she’s about to have sex with her boyfriend. She’s been asking me some more questions about sex lately. It’s clear she wants more information on what she should do. The problem is, I really don’t want to tell her anything about how to make sex good. I don’t want to encourage her to be having sex right now or to imply that it is fun. It took me almost a decade to figure out how to make sex amazing, and during that time, I didn’t have much sex. I’m happy I didn’t because I was not making a lot of good decisions early on in those years when it came to men. At some point, I hope that my daughter’s friends might help her figure out what to do in bed, but my friends and I didn’t figure it out very early either. I worry that if she tells me sex is bad and I don’t tell her how to make it better, she will resent me if she finds out all the things I know about great sex. What should I do?
To a degree I understand your dilemma, but the practical implications of your current approach would deprive your daughter of information as well as good sex. If she’s going to be having sex—and I think we all know that she is—why shouldn’t it be good? Why would you want her to stumble around in the dark or suffer? She’s developing, which means she’s creating the foundations on which her adult life will be built. A good handle on sex now will increase the chances of her maintaining one throughout life. That you hope someone else will teach her what to do suggests that you aren’t against her having a healthy sex life, you just don’t want the moral stain of being the one to help her achieve it. Well, I think of the enforced ignorance you are envisioning as its own moral breach. You had a long journey to understanding what good sex meant to you, and you seem to think your daughter should face the same (relative) hardship, but I’m not exactly sure why. Allowing someone to find their own way and inevitably make some mistakes, I suppose, could be character-building, but if you aren’t taking a tough-love approach and merely are operating on some if-I-had-to-she-has-to notion of fairness, let me assure you that the universe’s balance does not rest on maintaining this legacy of sexual ignorance. Principle for principle’s sake here is useless.
While I hope this gives you perspective and a different way to approach this issue, I understand that merely countering your principles with mine may be impractical in its own right. I also understand that ideas aside, actually conducting such a conversation might be daunting for its potential awkwardness. I feel that this is something to get over for your daughter’s sake, but at the very least you could point her in the direction of some online sex-positive resources for teens, like Scarleteen or Amaze. Make sure she understands consent and her ability to say no, and if she has any outstanding questions that you just can’t bring yourself to answer, send her our way.
Dear How to Do It,
Three years ago, I was diagnosed with genital HSV-1. At the time, I was about a year into a relationship with someone I knew had it orally. I’d known there was a possibility of gential transmission via oral sex but accepted that risk as part of our committed relationship. We broke up a year later, and since then, I have dated some and had sex with two new people, who were both cool about my “condition.” Despite the fact that I’m educated about this STI, and did not take it as a death sentence to my sex life, it has still affected my mojo. I’m a woman in my 30s, and not quite ready to settle down. Even though I’m not as gung-ho about casual sex as I was in my 20s (just because I need more meaningful connection), I still want to have the option. But knowing I’d have to have “the conversation” before each of these encounters just kills the mood, my excitement, and my motivation, before it even begins. My libido is definitely lower than it would be if I didn’t have this issue. This would be a fine situation for someone looking for serious inquiries only, but as someone looking for a medium level of seriousness, and just some of the spontaneity of my younger years, it’s kind of a hindrance. How can I reawaken my mojo, and my excitement for sex and dating?
You say you’ve refused to see herpes as a death sentence for your sex life, but you do seem imprisoned. I believe that confidence and motivation can be conjured, and this may be a moment where you just have to lift yourself up by your bootstraps. Yeah, it sucks to have such a cross to bear—especially an unnecessary, socially constructed one—but you’re going about your pursuits ethically. You have the option of daily valacyclovir to help lower the risk of transmission, which could ease the minds of you and your partners. Also keep in mind that in 2015, the World Health Organization announced findings that about two-thirds of the world’s population under 50 has HSV-1. You may feel stigmatized and alone, but you’re far from it. Take comfort in that.
Dear How to Do It,
My wife and I have been married for 14 years. The first 13 of it we lived in a repressed sexual state (thank you, Jesus). We finally started having open and candid conversations about sex, and guess what? Hot, fun, beautiful, amazing sex followed for both of us. Now that was a miracle!
One of the most helpful things for us has been using yes/no/maybe lists. I had no idea my wife was interested in so many things. We both share the ownership of that and have moved past the regrets of all the years we could have been exploring and are now on to living in the sexual moments of today. We are still learning and growing out of the repression, and some things are easier than others to try. Since this is a How to Do It column, can you help with something? One of the yes-no-maybe answers was she asked to have rough sex. I am very gentle by nature. So the first thing I did was ask her to help me understand what that looks like in her fantasy, to describe what is happening to her because everyone’s idea of rough can be different. As we talked through the list, her No. 1 desire is she said what she really wants is to be pinned down and thrown around the bed. In her words, it’s one of the things she constantly thinks about.
The “pinning down” part is something I can do. But the throwing her around the bed part … well … I am not strong enough. I have never been buff. I have issues about my body and I don’t feel very masculine. I have started a workout routine with an online trainer to try to help, but truthfully I don’t see myself ever able to be strong enough to lift my wife and it is frustrating. This request from her reminds me of how weak I am and I immediately feel I am not strong or man enough for her. Do you have any practical suggestions for how to engage in this desire of hers—to feel pinned and thrown around by a strong man? Do you have any other ideas or advice on how to tap into the strength she desires? I’m average height at 5’9” but just have always been so skinny. She’s the same height as me. Neither of those things can be changed—I’ll stick with the trainer for the health benefits, but based on my body, age, and where I’m starting, I don’t see real “throwing” around in the cards.
What if instead of picking her up, you sort of rolled her around? You can be pretty domineering about changing positions without having to lift her. Imagine you’re in a doggy position, and you shift to missionary, by rolling her over. You assert your own desire and strength, but both gravity and she can work with you to get into position. Otherwise, a sling might be worth looking into, depending on what is attracting your wife to being thrown around in the first place. Is it the very brute strength that would require such a thing, or does she like feeling a sense of weightlessness? If it’s the latter, a sling may be for you. If nothing else, it will make her more mobile overall.
I have to wonder what this person who’s been looking at you more or less every day for at least 14 years is reasonably expecting of you here. Barring a fetish for undisclosed or undiscovered strength, she must have some sense of your capabilities and that being thrown around by you may well not be physically possible. Is this her way of hinting at an interest in sex with someone with a larger frame? It’s great that you’re so communicative, greater still that you’re so invested in her pleasure that you’re willing to alter yourself for its sake, but I’d suggest you have another conversation to tease out exactly what she’s asking of you. It shouldn’t be the impossible.
More How to Do It
My never had sex before we got together, not even masturbation, because of her conservative upbringing. We enjoyed ourselves the first few years. After that, she seemed to lose interest. I think she had a few real orgasms, but mainly faked them. I always suspected this was because I am not very big—I’m about 3.5 inches erect, and I tend to ejaculate quickly. I told her she could try another man, since I had 13 to 15 sex partners before we were married and she had none. I wavered on this a few times as I got insecure and jealous, but in one of my more permissive times, she met a man and liked him. I tried to call it off, but she wants to go forward. Should I let this happen? I’m afraid he will be much bigger and she’ll enjoy him better.
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