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,
Just over a year ago, right before the pandemic, I dated a guy I met on a work project for a month or so. Long story short, over the course of a few dates he showed himself to be quite nice, but in retrospect, with a huge number of red flags. The biggest red flag was when he was driving me home one night after a dinner out, and he slowed the car down as we were driving through a deserted street with a bunch of empty warehouses. He pointed at one of the warehouses and said, “What if I were to pull you in there, and … ” I was shocked and immediately asked: “And what?!?” He kind of smiled, and said in a strange way, “Murdered you.” At the time, I laughed. I was so surprised that I think my brain told me that he couldn’t possibly be serious. I countered that I would fight him if he tried anything, and we continued driving.
Our dates fizzled out, without ever getting physical, and in the year since, I have wondered whether his red flags were indications of some serious danger. I have also felt embarrassed and ashamed that after he made such a horrible statement to me, I went on two more dates with him. Not to mention all the other bizarre things that are too many to get into, but that showed him to be reckless, manipulative, and even sadistic. I suppose I was waiting for him to show me a better side that I hoped was there. Nothing terrible happened to me with him, but it could have. I don’t want to get into that situation again. The experience with him has made me seriously question my own judgement.
Do you have any advice about how to go about dating after being so wrong about someone? I’m a woman in my early 20s, and I feel scared that I too easily explain away disturbing behavior. Where’s the line between giving someone a chance and backing away? How do I tell whether someone is socially awkward with a weird sense of humor or someone who will drag you behind a dumpster? I always thought things would be obvious and that gut reaction is enough to save you from the worst creeps, but I’m worried about my ability to judge others.
—Scared to Date Again
You, in your early 20s, gave more chances than you’re comfortable with. I did the same, and now, in my mid-30s, generally give fewer than is probably fair to the individual. By 20, my roommate at the time and I had a list of questions we asked potential suitors: Do you deal drugs (and yes, marijuana counts)? What does no mean to you? How old are you—really? Do you understand that condoms are meant to stay on for the duration of vaginal penetration? Writing this out, I’m feeling pretty bleak about humans, because each of those questions has some wacky, inappropriate story behind it. And that list didn’t do much, because they’d ace each question and then provide us with a new one to add that we hadn’t anticipated. And, lest you think this is all men, there are stories of women caught sniffing through my panty drawer, using the child locks to trap one of us in a car, and other bizarre behaviors. Some lucky people never experience a hint of this. You, and I, and most of the people I know, though, have at least one horrifying tale.
“Socially awkward with a weird sense of humor” and “person who might drag you behind a dumpster and kill you” aren’t mutually exclusive. They also aren’t mutually inclusive. Cool, calm, and collected with nary a hint of red doesn’t necessarily mean safe to relax around, either. Dating, and sex, are inherently risky. We can take a number of steps to reduce our risk, but we can’t lower it to zero. Sex workers who provide direct services have something called a “bad date list” that helps weed out bad actors, but that isn’t feasible for recreational dating.
When I go on a first date with someone, I tell my roommate where I’m going and when to expect me home. If I’m feeling particularly twitchy that day, I’ll show him a picture. And if things look like they’re going to get sexual, we go to my place, where my roommate is within earshot. I wear shoes I can run in. And I’m reluctant to get into other people’s private cars. As a relationship progresses, I leave things at the other person’s apartment that I’m prepared to lose—ratty underwear, a toothbrush, and other things I won’t feel the urge to gather if I need to leave quickly.
For your specific situation, I think you should take all the time you need. What happened to you is disturbing, alarming, and gross. When you’re ready to date again, start slowly. You don’t have to go on all the dates. You don’t have to go on any dates. If therapy is an option for you, do it—you can work through whether your justification of his behavior is part of a pattern, and you’ll probably grow in other areas, too. Another thing you can do is talk with your close friends about the people you’re seeing. Sometimes an outside perspective spots trouble before we can see it. Crucially, you have to listen to these friends—if you ignore their advice, they’ll stop giving it. And if something happens with someone else, and you aren’t sure about them, feel free to write back in.
In the meantime, remember to breathe. Take care of your body—get enough sleep, enough water, enough vegetables. If you have some physical practice—yoga, running, core work on your bedroom floor—keep doing that. If you don’t have one, now’s a great time to start.
Dear How to Do It,
My wife and I have been in a happy, monogamous marriage for 28 years and are both in our mid-50s. In the fall, as the pandemic restrictions hopefully ease, we will become empty-nesters, as our youngest son leaves for college. We have talked about many ways to spend our newfound time, but fortunately for me, one that my wife seems open to is to fulfill some of my hotwife fantasies. She is certainly more than able to pull this off, as she is very beautiful and a naturally flirty and gregarious person. She has just one small hang-up: Seven years ago, after being diagnosed with breast cancer, she opted for a double mastectomy. It was the completely right call, and she has been healthy and cancer-free ever since. The doctors also did a fabulous job on her reconstructive plastic surgery. Seriously, she has the tits of a 20-year-old, with the exception of nipples and some very small but noticeable scarring. While I have found no loss in her sexiness, she is worried that men will be turned off by the lack of nipples. I have told her that men look at an entire package, of which breasts are one small part. Also, if we were to use an app for these liaisons, I figure we can be upfront about it, and if she were to meet a man in person, being honest might open a conversation to get the action going. It also makes her worried that the men she may attract would be fettishest themselves and objectify her.
While this fantasy of mine is something I would love to pursue, I definitely don’t want to do anything that would make my incredible wife feel uncomfortable or lessened in any way. Any suggestions for us?
Dear Nip Slip,
I have tentative congratulations for you! A happy 28-year marriage is a wonderful thing. And exploring something new can be delightful. Why are my congratulations tentative? No matter how much you try to mitigate the reactions of closed-minded men, there will likely be at least one total jerk who doesn’t read or hear the mention of your wife’s nipple-free breasts and freaks out about it. And there will almost certainly be people who fetishize or otherwise objectify her. Dating is a gauntlet.
Let your wife do this in her own time. Listen to her concerns, validate them, and tell her what kind of support you can offer when things go sideways. Respect her choices about who to proceed with and who to bail on. When she seems uncomfortable, remind her that this can stop at any time. Allow yourself to be excited, for sure, but don’t let your desire for sexual fulfilment get in the way of your own ability to see your wife as a full, vulnerable person. It might help to make a list of all the things you love about her that have nothing to do with sex or her body, to refer to if you start sliding into fantasy land. Another list that might be useful is the behaviors and speech patterns that let you know she’s feeling anxious or exposed.
I imagine that the two of you have built a ton of mutual care, respect, and understanding, and that you’ve developed some skill at having difficult conversations. Turn to that knowledge when things get rough or sticky. Remember that you love each other, and protect that.
Dear How to Do It,
My wife and I have a wonderful sex life—we’re middle-aged and make love twice a week. But I worry that sex is more emotional for me than for her. I am always saying “I love you” before, during, and after, but she is much more straightforward about it. When I tell her how precious her orgasms are to me, she replies, “Yeah, great, my orgasms are precious to me too.” I love her feminist, pro-sex swagger, but sometimes she doesn’t realize how the lack of emotional reciprocation hurts. I can’t bring this up without complaining about what is otherwise a wonderful thing. Asking for more emotion isn’t as easy as asking for more lube. How to talk about this?
Dear Love Hurts,
What you describe certainly sounds like sex is less emotional for your wife than it is for you. How much of a dealbreaker is this for you? If you need to be told you’re loved verbally during the act of making love, that’s important to communicate. Speaking of verbal communication, you don’t mention whether she says other things during sex that are expressive. Some of us aren’t naturally talkers when we’re touching bits, and that’s OK. Some of us see sex as more of a physical activity than spiritual, and that’s also OK.
“I can’t bring this up without complaining about what is otherwise a wonderful thing” gives me pause. Are you able to have direct conversations with your wife about your needs? If you aren’t, that’s a much larger issue. If you are, where is this framing coming from? Does it stem from childhood? Were you in a controlling relationship at some point before you met your wife? It’s important to figure out how much of this is because of her behavior and reactions, and how much is due to your history, so you can unpack what’s happening inside your head and move forward in the appropriate manner.
So, how to have this conversation: “Dear wife, as you know, I’m a squishy, emotional person. I’m feeling frustrated when my declarations of love mid-act aren’t reciprocated [or however you want to say it], and I’d like to have a conversation about that. Can you help me understand what happens on your end when I say I love you while thrusting?” From there, listen. Pay attention to what she’s saying, how she’s saying it, and what her facial expressions are doing. Ask gentle follow-up questions if you aren’t sure you understand or when you want further detail. Be prepared to answer questions yourself, too. Do all the things to set yourself up for success: Pick a calm moment when everyone’s biological needs are met and there’s plenty of time to talk without interruptions. When I say plenty of time, I mean a couple of hours. And, if the first conversation goes poorly, take some time to figure out what went wrong and try again.
Dear How to Do It,
I am a 30-year-old queer woman who has dated across gender identities and has had two serious relationships (three years or more) with two straight men. I am currently still in that second serious relationship (he is 40 years old). I am wondering to myself whether I just should not be with cis hetero men anymore, because I am finding myself having the same sexual issues.
When my current partner and I met three years ago, we had just gotten out of long-term relationships where the sex had severely stalled for years. We both felt an attraction to each other we had never felt before, and our intimacy was amazing. We spent a lot of that first year together speaking openly about how we knew that eventually, the brain chemicals would stop making our sex so easily exhilarating, but that we would always be open and committed to keeping the flame alive.
We are now in year three, and I am infuriated with him because it seems like he never meant what he said. I used to really feel my partner’s desire for me, but now his kisses and touch feel so languid. There’s no more variation in intensity, whether in kissing, touching, or penetration. I have tried for two years to bring this up with him, but the few times I have, he becomes so defensive and eventually apologizes, but I just don’t even feel I can be open now about my feelings. He will say things like “There’s so much I do, but you focus on the negative.” Or a really bad one that he apologized for was saying “Well, we have more sex than you and your ex ever had.” He always frames things as “I promise I’ll be better,” but all I want is for us to speak more openly, and for him to be honest with me about where he is at.
My partner is affectionate and sweet to me every day, but there’s no more sexual edge to it. I am stuck thinking that I am more attracted to him than he is to me. I now feel so resentful that mid-blowjob or handjob I feel full of anger. I do want to pleasure him, but then realize that I will just be disappointed when he either does not reciprocate or does, but without any intensity or desire. I am frustrated with myself for being in this space again, where I feel unattractive, unwanted, and unheard. I keep wondering whether cis men are too defensive to be long-term, satisfying sexual partners.
—No Mo Hetero
Dear No Mo Hetero,
Anecdotally speaking, heterosexual cisgender men are generally, bizarrely rigid about what sex is, how it should happen, and what it should involve, which becomes boring for those of us who lean more queer. Gormless comes to mind. Like, how many paint-by-numbers blowjobs can a person give before they want to cry from tedium? Your dude is inhabiting the stereotype.
I know it’s difficult to rank desires and needs, but that might be your next move. Spend some serious time thinking about what you want and need, putting each item on one of two lists as it comes up. Once you’ve got a pair of exhaustive lists, rank each in order of priority. This will also give you an opportunity to re-think whether an individual line is a want or a need. Take a week off, and then compare your hierarchy of needs to what your guy actually gives you. If it’s too much of a stretch, move on. If the intimacy, support, and love you experience are more important than what you’re missing, it’s worth a conversation.
Ask your partner what sex is to him. Focus on hearing his perspective and sharing yours, with the goal of working out how the two of you can relate sexually to each other. Areas of overlap are great, and areas where one or both of you can stretch a little are also useful. Once you’ve had that conversation, evaluate, again, whether that’s enough for you. Presuming it is, some education through books or films might help. Highlight passages, or note time codes, that show interactions or specifics that you find arousing. Show or read them to him. I suspect that a lot of this hetero cis male rigidity is due to lack of models for other options. The mainstream porn feedback loop of patriarchal penetration, where sex follows a certain pattern, and the dominance of that pattern in the most easily found material leaves more creative and fluid work like that of Shine Louise Houston and Chelsea Poe on the sidelines. I hold hope that his mind can be broadened.
If you decide you’re done with hetero cis dudes, that’s OK. If you decide to focus on meeting other queer folx and feeling out whether you’re as romantically inclined that way as you are sexually, that’s OK. If you decide to stay open to dating people of all presentations, that’s OK too. It’s your life, it’s your choice, and you get to decide.
More How to Do It
I’ve recently become “official” with a guy I’ve been with for a few months (hetero, in our 20s). He’s a little bro-y, you could say. Not my usual type, but he’s quite sweet and attentive to me behind closed doors, especially in bed. However, there’s one thing that keeps getting to me: He often says things about other women that are crude at best and misogynistic at worst. Every time he does this, I shut it down and tell him that’s an unacceptable way to talk about women, and he always seems genuinely surprised, agrees with me, and apologizes. But I wonder if I’m too easy on him because I want to be with him and he doesn’t treat me this way. What do you think?