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 am a 42-year-old woman, and I’m a virgin who has never dated. I can’t even believe I wrote that because I am deeply ashamed of that fact. I won’t go into all the reasons, but I will say that I have had severe anxiety since I was a little kid. I am in treatment and on medication, but it has a very strong hold on me. Amazingly, it’s actually better than it was, but my problem is that I’ve let my anxiety run my life for so long, that I have never dated. And I had hookups and that kind of thing, but I always refused to have sex because I never wanted to fuck someone I didn’t know. I wasn’t waiting for marriage. Just waiting for someone who wasn’t a stranger. Please know that I understand confidence is sexy and all that.
However, my biggest fear is that men will learn I’m a 42-year-old virgin and run for the hills. I’m afraid they’ll see that as a huge red flag, so that creates this cycle where I’m afraid to date, but the longer I wait, the longer I’m still a virgin. I know that I can’t control how other people think, but I truly fear that maybe I’m really not good enough for anyone. I get the feeling the response to this is going to be “Keep going to therapy.” And I get that. I know that I have emotional issues, but my real question is, how do I address the fact that I have never dated or had sex if I do try to start dating? I feel like any answer I give as to why is going to sound pathetic, and they’re going to go to the bathroom and never come back.
Dear Lonely Virgin,
Here’s the thing—someone, at some point, might be a huge jerk. Someone might be exactly as awful and judgmental as your anxiety is saying they might be. I’m not going to send you out there with false comfort. So, you might ask your therapist to work on ways to handle it in the event that someone is a jerk. Get prepared for the worst-case scenario. Roleplay things you might say to shut down nasty commentary or to extricate yourself from a situation you want to leave.
Dating is a process of being rejected over and over again until you find someone who wants to pick up what you’re putting on the table. A big factor in how many times you’re rejected before that happens is luck. And, of course, you have to also be interested in the other person.
How do you address your virginity, though? Directly, and in your own voice. Put “I’m a virgin” in your own words. Maybe that’s “I’ve never had sex,” or “I was too busy doing ____ to date, much less get dicked,” or even “Weird fact about me, I’m a virgin.” Practice with your therapist, or friends, or at gatherings of people where discussions of sexuality are appropriate, if you think that’ll help. But you also might rip the Band-Aid off and see what happens.
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Dear How to Do It,
I am an asexual woman in my 30s who has never had sex with another person. I masturbate periodically (a couple of times a month) because it’s relaxing, but I don’t miss it when I don’t. I’ve never been sexually attracted to another person, but I find BDSM erotic and that is what I think about when I masturbate. I’m married to another asexual woman who I love very much. I’m starting to be curious about partnered sex, especially involving d/s dynamics or bondage. My partner has previously mentioned potentially being open to exploring sexuality together, but she has a history of sexual trauma that she has had therapy for in the past (she does not have interest in restarting therapy, since she doesn’t see it as currently affecting her life). This history means that she starts crying involuntarily whenever we talk about this. Before we married, we agreed that we would be willing to sexually open the relationship if one of us wanted to. I love her and would love to explore this with her, but I am concerned about bringing it up to her because I’m worried that I’m more interested in the idea of sex than the reality of it, and I don’t want to cause her distress, especially if it may be for nothing.
I have multiple questions: Is there a way to know if I’m actually interested in sex or just the fantasy of it? (I worry in part because some of my fantasies are nonconsensual on my part, which I recognize is very common and not a sign that I actually want to experience sexual assault, but I worry that my interest in consensual sex is the same.) Is there a best way to bring this up with my wife? If she would rather open the relationship, is there a way to find a woman for a kinky hookup or friends-with-benefits safely, especially if I think there’s a significant chance I’m going to chicken out? How much should I disclose about my sexual (in)experience? I understand that you are not magic, but any thoughts you have would be appreciated.
Thank you for understanding that I’m not magic. I appreciate that.
Your wife starts crying involuntarily when you even talk about opening up. This is not a good sign, and usually not a good place to be opening your relationship from. If you’re wanting this so much that you’d leave, the ultimatum route of “work on this, therapy or no, so we can have a real conversation about it, or I’m going to love you from the distance of having divorced” might be the way to go, albeit a harsh option. If not, wait it out while letting her know that you do want to be able to have a real discussion about opening the relationship and asking how you can support her in being better able to have that talk.
Unfortunately, there’s no way to know for sure whether you’re actually interested in sex until you’ve tried it, or at least been in a position to do so. Even then, it’ll always have been possible that it wasn’t the right time, or person, or weather that day. You can dive in headfirst and try everything all at once—which really does work well for some people—but I’d advise you either start with one single activity that appeals to you the most or land somewhere in the middle. So you might say, “I’d really like to kiss, and try eating you out.” Or, “I’d love to be penetrated by your toe, and that’s all I want to do at this time.” Your specifics may vary! Just remember: “Safe” sex is a misnomer, there is only safer, and to comment on that I’d need more information about what is unsafe for you. Do disclose your experience level, along with your interests, as it feels appropriate (before you get down to doing it). Whichever way you decide to play it, I think you’ve got this.
Dear How to Do It,
I’m a woman in a long marriage. I miss sex so much. We are in our 60s, work full-time, and generally have a good life. My husband has some health challenges that mean that Viagra no longer works and possibly isn’t safe. I’ve asked if we could have more physical encounters for me, and he agrees but it happens very rarely, and when it does, I’m so afraid to do anything that might stop him that I can’t ask for what I want. We sleep separately, so spontaneity isn’t really a thing. Yes, I have sex toys and use them but it isn’t the same. I miss loving and cuddling and being physically wanted. I adore my husband and dread hurting him. I’ve sort of accepted this part of my life is more or less over but it’s hard. I wish I could adjust better to this. Any advice?
First, let’s separate the loving and cuddling from the sex. You can have all the love and cuddles without him having an erection, or him performing oral or digital sex on you. Get that. Ask for it, tell your husband you need it, and make it happen.
As for the sex, have a pre-conversation where you let him know that you appreciate his efforts and are also feeling anxiety around communicating what would make them most engaging and fulfilling for you. Tell him that you’re afraid to hurt him, or put him off the endeavor entirely. Share what you’re feeling with your partner in life. Ask him to hold you while you use your toys, too. You’re within your rights to ask for what you want.
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