I’m a Divorced Mom Who Just Started Dating Again. I’m Very, Very Embarrassed by One Thing Everyone Is Doing These Days.

How to Do It Photo illustration by Slate. Photo by nd3000/Getty Images Plus. Our advice columnists have heard it all over the years—so we’re diving into the How to Do It archives to share classic letters with our readers. Have a question? Send it to Stoya and Rich here. (It’s anonymous!) Dear How to Do It, I’m a divorced mom, and I recently started dating. I love being on the apps and have made some great matches. A couple of these got very sexy very fast, and there have been some scorching-hot text exchanges with one guy in particular. I don’t send nudes, and I don’t send any compromising photos that show my face (the photos I do send are pretty tame anyway—just underwear shots). But I love sexting and am a very eager participant in these conversations. But there’s a catch. I feel very, very ashamed and guilty about these conversations. I know intellectually that we are all consenting adults, and that there is absolutely nothing wrong with what we’re doing, but I cannot shake the bad feelings. Some part of this surely relates to my work—my job entails preventing and responding to incidents of sexual harassment and assault, so I spend all day every day thinking about all the worst-case scenarios. And some part is clearly how women are socialized to think: Even though my parents were pretty liberal, negative societal messages about female sexuality still clearly affect how I think. And I’m mildly kinky, which is also a source of deep embarrassment that I’m just now starting to overcome, and that makes me feel even worse. So what do I do? I love these conversations and get very turned on by them, but the negative feelings swirl in the background and keep me from fully enjoying myself. —Secret Sexter Dear Secret Sexter, You’ve got a broad-strokes idea of what’s going on for you emotionally—some part surely relates to your work, some part is clearly socialization—and I’m wondering if further detail and clarity around that might help. The next time you’re having these negative feelings, listen to them. If there’s fear, what is the fear of? If you’re feeling self-judgment, what exactly are you judging? With a more granular understanding, the hope is that you’ll be better able to think through the tension between your intellect and your emotions. For instance, worst-case scenarios. What are all the worst-case scenarios, what can you do to mitigate each, and is there anything you can do but aren’t already doing? Either knowing you’re doing everything you can or implementing the missing strategies and then having that knowledge seems like it would help. Recurring messages about female socialization can be an opportunity to compare these internalized rules with our own beliefs. You might find that practice helps on its own, too. Exposure to discomfort can increase our ability to tolerate it, and there’s something about successfully doing the thing we’re afraid of that decreases fear. —Jessica Stoya From: I May Have Lied to My Boyfriend About My Real Relationship With My Best Friend. (May 25th, 2021). Please keep questions short (<150 words), and don‘t submit the same question to multiple columns. We are unable to edit or remove questions after publication. Use pseudonyms to maintain anonymity. Your submission may be used in other Slate advice columns and may be edited for publication. Dear How to Do It, I’m a 32-year-old woman. I recently started hooking up with a new guy. Things are pretty good, except for one point: anal. He absolutely refuses, under any circumstances, to do me in the butt. He says some nonsense about not finding anything erotic about the tube where shit comes out of. I do enemas fairly regularly and can assure you, my behind is clean. No amount of logic or appeal seems to penetrate his prejudices, and it’s a damn shame, since I do otherwise like him. How can I get him to see the light? —Need a Real Man Dear Real, I am not going to help you coerce your guy into sex he doesn’t want. When you sign off with “need a real man,” it sounds like you don’t respect men who won’t penetrate your anus, and if that’s the case, the kindest thing to do is break it off with this guy and find someone who wants the same things you want. —J.S. From: My New Guy Won’t Do What I Actually Want During Sex. I Know a Real Man Would.(November 30th, 2021). Dear How to Do It, I’m a lesbian and I’m 27 years old. I’ve also never had sex with a woman. I’ve made out with many women, I’ve had fun with boobs, but I’ve never touched or seen a vagina. I’m turning 28 soon and I feel like the clock is ticking. The older I get, the more worried I am about how partners will react to my being inexperienced. The other thing is that there seems to be so many labels on sexual identity, but none of them seem to fit me. I don’t ever want to be penetrated with a strap on and really want to be the giver in that aspect, but I love being fingered and receiving oral (at least I did with men). I obviously don’t know how I feel about giving those things, but that’s another part of what makes me nervous! I’m so worried I’ll start to go down on someone and either be bad at receiving directions or, my worst nightmare, not like the taste. I guess I just am overall worried that I’ll get in the bedroom, be too demanding, and also not know what I’m doing and it’ll just turn them off completely. It’s made it hard for me to date because I get so nervous about what might happen that I can’t act normal and it ruins everything. I just want to get the first time over with at this point. —First Time Dear First Time, Breathing can be super helpful for reducing anxiety. There are many techniques. One that works well for me is to inhale for four counts, hold my breath for four counts, exhale for four, and hold again for four. A couple of purposeful breaths are something you can do at any time. You don’t have to close your eyes or go somewhere quiet. You can simply breathe wherever you are, and the people with you probably won’t even notice. The communication skills you’ve developed with other partners are likely to transfer well here. It might be worth taking a look at the internal structure of the clitoris to get a refresher on where the parts most likely to be fun are. That said, vulvas vary just as much as penises, so you’ll still want to ask the other person what they like, and experiment within each others’ boundaries. Your nerves might make it more difficult to be in the present moment and focus on the femme in front of you, so work on that breathing and any other soothing techniques you have. If your attention wanders, calmly refocus yourself. ariance, each person has their own taste that can change according to where they’re at in their cycle, the amount of time and physical activity since their last shower, and other factors. Not everyone likes everyone else’s taste. In this column, we’ve heard from one person who believes they detect nicotine through oral sex. If you have a vulva, you can check out your own secretions at various stages of arousal to get a basic idea, but I really want to underscore that there’s a whole literal half a world world of pussy nuance and divergence out there. You might think of it as somewhat like wine—it all tastes the same, and also not at all. You may be rejected more, and possibly more harshly, but I do think it’s useful to disclose your experience level. Think about how you’ll frame it positively: “I’ve loved breast play, and am really excited to experience sexual connection involving a woman’s genitals.” If you’ve established chemistry and interest, you might say something like “I’m super into the idea of penetrating you with a strap on. It would be my first time, and I’m looking forward to something new.” Find the phrasing that feels most comfortable for you, and consider practicing in front of the mirror or with a trusted friend. —J.S. From: My New Guy Won’t Do What I Actually Want During Sex. I Know a Real Man Would. (November 30th, 2021). More Sex Advice From Slate I am a mid-30s woman, and I’ve been with my boyfriend for going on a year and a half. Last week, a friend messaged me, saying she had to tell me something about my boyfriend. Well, turns out he was active on Tinder. I was shocked and confronted him almost immediately. At first he denied it, but he eventually came clean … about everything. Never miss new Slate Advice columns Get the latest from Prudie and our columnists in your inbox each weekday, plus special bonus letters on Saturdays. Advice Dating and Relationships Sex