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 bisexual man in his mid-twenties. I was attacked by a man during a one-night stand in college. After that, I stopped having sex with men for a few years and only had sex with women. I also got in really good shape to try to help my confidence, but I still didn’t feel comfortable having sex with men until I met “Ellis.” Ellis is calm, smart, and considerate, and I love that he’s really kind to me and everyone he talks to. I felt comfortable around him as soon as we met, and we started dating. It’s been a year now. I’m comfortable having sex with him because, even though he’s taller and mostly tops, he’s very thin and I could defend myself if I needed to. I feel bad thinking that—like the only reason I feel comfortable having sex with him is I could hurt him if I had to.
What’s weird is I do enjoy it, we have great chemistry in bed, just if I start to feel nervous during sex, I picture how I could defend myself. But I don’t want to hurt him, in fact I’m starting to think Ellis might be “the one.” These thoughts are starting to make me not want sex. I haven’t told him about what happened yet, and I don’t even know where to start with how that has made me feel about sex. I’m terrified he’ll leave me if I tell him what I’ve been thinking. I also think he’ll be upset I didn’t say anything earlier and feel like I don’t trust him.
Ellis’s hypothetical reaction within the imagined conversation about your assault you mention at the end of your letter is a projection. It’s 100 percent the product of your thinking. It has no more bearing on reality than the many and several extended back-and-forths I have with my cat. Your trepidation is understandable and certainly you are entitled to your feelings, but please don’t make decisions based on what someone might say, especially when that projection is a pretty bad-faith reading of a person whom you otherwise describe in such superlative language. If he is as kind as you say he is, there’s a good chance he’ll hear you out instead of immediately opting to leave you, if and when you’re comfortable revealing your trauma.
I think you should also reframe your consideration of his stature. His wispiness may help you feel comfortable, but it is one attribute among many that you appreciate about him. Packed into that wiry frame is someone whose intelligence, kindness, and calmness you’re also attracted to. Even if it sometimes feels that way, the picture you paint of your relationship suggests that your perceived ability to defend yourself against him is far from the only reason you feel comfortable having sex with him.
By the way, what kind of work have you done on your trauma? Have you seen a therapist? Have you read anything? Have you at all attempted to work through it? You only mention exercise, and it’s pretty obvious to me that you have more to resolve and may need help doing so. Look into that. It’s exponentially unfair, but unresolved trauma may play a role in relationship issues. At the very least, you don’t want to make your boyfriend your therapist—that may be a stressor on your relationship. Seek outside guidance if at all possible.
Dear How to Do It,
I’m in my early 40s and returning to dating after my divorce. I’ve been having a great time on dating apps, but I’m wondering if I’m having sex too soon with these dudes. I’d always thought that there’s no reason not to have the sex you want to have, whether that’s the first date or the 10th date, and that if it’s the right person, it won’t really matter how long you wait or don’t.
But I have noticed what I think is a trend among these guys where they get into a “sex pursuit” mode—they can’t think about anything but you, they’re crazy about you, you’re the most amazing thing ever—that ends after you’ve had sex a few times. That’s cool and fun, but I wonder if there’s an argument to be made for waiting to have sex. I didn’t plan to become traditional in middle age, but maybe there’s a good point to not doing it right away. So my question is, does waiting to have sex make it more likely that something becomes more serious instead of just a fling?
—Traditional in Middle Age
Dear Traditional in Middle Age,
The decisions made in any process—in this case, that of finding a mate—will send certain signals to the receiving parties. How those signals will be interpreted, however, is a crap shoot. One person’s policy to wait a certain period of time before sex could be read as a signal of seriousness from one potential mate and a sign of disinterest from another. That interpretive variation makes establishing monolithic rules very difficult—although that seemed of no concern to Ellen Fein and Sherrie Schneider, the writers of the notorious dating how-to book The Rules, who suggest waiting a few months. Warning against sex on the first or second date, they wrote: “Why risk having him call you easy (and think of you that way) when he’s talking to his buddies in the locker room the next day?”
The big problem with that logic, as I see it, is that it advocates pandering to someone who would slut-shame you over valid, pleasure-seeking choices. If that person has toxic attitudes before he gets to know you, he may very well carry remnants of them through a relationship. Move in with him and you may be inheriting stigma along with some new furniture.
If your goal is merely to lock someone in so that you won’t be alone (and then, if you’re really optimistic, hope that any kind of incompatibilities will resolve through the magic of the love between you), I can see why such a strategy could be tempting. If you’re actually looking to spend time with a person that suits you, a better choice will be a more straightforward approach, in which you lead with your love of sex and interest in having it. One risk there, though, is that when you do start sex early, you may be setting a sexual tone and the relationship may not flourish from there. Unless there isn’t conscious balancing quickly, the other person may think you just want to be fuck buds.
Remember, there’s no guarantee that anyone will stick around after sex, no matter when you have it. The same disinterest you fear might set in two months into your dating, if that’s when you finally decide to do it, as it would have after two hours. You just never know, and there’s no cheat there. You just have to go through it. I can tell you that anecdotally, I’ve had sex with all of my long term boyfriends practically immediately—on the first date, if what we were even doing could be called dating. Of course, there are many more people that I slept with and never saw again. Perhaps they could have become boyfriends if I took a different approach, but oh well! I’ll never know what I missed out on there, and I’ve had fulfilling enough relationships that I don’t really care.
With all that said, there is some data to support the power of waiting—a 2012 study out of Cornell suggested that, “Women who have sex early in a relationship are more likely to be dissatisfied later with the quality of the relationship, because sex may have greater symbolic value for women as an indicator of the relationship commitment than it does for men.” This conclusion doesn’t prove or disprove your question about whether sex early on will facilitate or impede a relationship, though. A more recent study pointed to the importance of sexual desire in the formation of relationships. Though it’s not exactly a newsflash to me, the science says that one good way to detect whether that all-important desire is mutual and strong is to have sex.
But you have to figure out what works for you. Maybe the cycle of sleeping with a guy immediately, not hearing from them, and then finding another guy to start the process with again, is daunting or exhausting and you need to set a slower pace, in which case waiting could certainly provide that. If you think you need more time, take it. Having a set process can be very important to accomplishing goals. And even when your reason for continuing said process amounts to confirmation bias, it’s a way of organizing the chaos of dating. I don’t think, though, you’re going to find a foolproof plan. People are too varied for that.
Dear How to Do It,
My girlfriend pursued me very intensely from the month my previous relationship imploded, to the point where I actually never had sex with anyone else in between. It’s been about a year, and this is the most secure, loving, and deep relationship I’ve ever had. Unfortunately for me, it’s a closed relationship, and she’s made clear that non-monogamy is not for her (she says she’d do it to “keep me” which is the same as no to me). I miss sex with other people, and I especially miss sex with other men. I know she’s uncomfortable with the idea of other men specifically, because I’m pan and she has worried I’ll prefer them because I had more boyfriends than other partners before she came along.
I’m struggling to decide whether or not I can stay in this relationship that’s so perfect in so many ways, but missing this key. I’ve been monogamous in some relationships before, so I know I can do it. How do I know I’m not just missing what I can’t have? It feels stupid to throw away so much closeness and someone that I sometimes dream of growing old with, but I crave novelty and the excitement of knowing someone new I’ll never see again, and also dick.
My pros and cons list feels stupid. How do I figure this out?
— So Close to Perfect
Dear Close to Perfect,
You are missing what you can’t have, but I suspect the most crucial concern here is whether it’s an actual bodily desire that isn’t being tended to, or if you feel this way for some less immediate reason, like the principle of just not wanting to be locked down. If the nature of your emotions is unclear, you’re just going to have to spend more time with them. Sit with them. Journal. Meditate. This is not work you can outsource; it’s entirely internal. Do you tend to be more principle-oriented or a pragmatist? If it’s the latter, then you can trust that your motivation isn’t simply rebellion, though we all have the capacity to surprise ourselves, and certain realizations may have you wondering how well you knew yourself prior to them.
If you sit with this for longer and find that your cravings aren’t subsiding, that’s only more reason to trust your gut. If thinking about other partners and how your current situation does not allow remains at the forefront of your thoughts, at a certain point it will qualify as a distraction (if it isn’t one already). You may not find a remedy that works more effectively than pursuing outside sex. It just may be the right option for you.
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Dear How to Do It,
I’m a mid-30s woman who’s been with my husband for 15 years. Early on, my husband asked me a handful of times to try anal sex. I did try it once with him but we went right to penetration since neither of us knew what we were doing, which was obviously not enjoyable at all for me. I always said no after that because I went on to develop internal and external hemorrhoids for unrelated reasons. (He has respected my no and stopped asking.) The hemorrhoids do not currently cause any problems for me but are definitely there, and I’m afraid of causing issues by being penetrated.
Fast forward many years, and we have opened our marriage. I’ve met a man who has lots of experience initiating women gently into enjoying anal. I’m so curious about exploring this with him. He insists my anatomy won’t cause a problem, and I’m wondering if that’s true. I’m also wondering if this would be a huge rejection of my husband, as this is something he’s wanted to do and I’ve essentially never agreed.
I don’t NEED anal in my life and am so interested to try, but not at the expense of my husband’s feelings. We opened the marriage at my request, and he has come such a long way to get on board for me that I feel like this could be unnecessarily hurtful for him.
— Is It Worth It?
Dear Is It Worth It,
I don’t think you should feel bad about wanting to try anal with an experienced partner. What’s great about being open is that it theoretically allows you access to things that you may be lacking in your primary relationship. Viewed practically, having anal with this guy amounts to enlisting a specialist to perform his specialty (that is, if he is as good at opening women up as he says he is). I love my boyfriend, but he’s not allowed to cut my hair. That’s what barbers are for.
I’m not sure what the parameters of your agreement are, but if you don’t have a must-tell clause, don’t tell. Your husband doesn’t need to know everything unless that’s been specified. Additionally, if anal goes well with this other guy, perhaps you’ll learn more broadly how to relax to enjoy it with other partners—your husband included. This guy could ultimately be doing your husband a favor by putting his dick in your butt. Ah, modern living.
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