How to Do It

I Have One Rule About Condoms

Why do so many guys break it?

GIF: On the left, legs tangled in a bed. On the right, neon condoms are illustrated.
Photo illustration by Slate. Photo by Artem Peretiatko/iStock/ Images Plus.

How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to howtodoit@slate.com.

Dear How to Do It,

I’m a straight woman who has a reoccurring problem with new sex partners. I insist on condoms for penetrative sex unless a relationship becomes exclusive, but I’ll engage in oral and light non-penetrative genital-to-genital contact without them. I’m well-aware those activities are not risk-free, but that’s my comfort zone. My partners are generally on board with wrapping it up at the beginning of the act, but sometimes they’ll take the condom off midway through because it diminishes their sensitivity. No one has ever slipped his penis back in pretending it’s still wrapped. The good eggs have accepted stopping for the moment, or engaged in petting or oral instead. But too often my partner has agreed not to enter me unwrapped, but will then rub his penis against me in a way that feels great and is essentially like knocking at the door begging to be let in. I’ve sometimes relented against my better judgment because I’m overcome by desire and I don’t love the feel of condoms either. One guy suggested we just do hand stuff instead, but then once I was really lost in the moment, he slipped his penis in without a word. I went stiff, and stopped it immediately, and never saw him again.

The culminated effect of these encounters has been to drastically damper my pleasure once the condom comes off. I feel hyper-vigilant about protecting my reasonable boundary, preventing me from letting go. I also feel resentful that it falls to me alone to keep the safe sex practice we originally agreed on, guilty and ashamed that I’m not getting him (and often myself) off, and sexually frustrated because I prefer condom-free sex too and it’s literally being dangled onto me. How do I reinforce this boundary without killing the mood with accusatory forewarnings or by creating an air barrier between our bodies? Or should I just jump out of bed and into a cold shower once the condom comes off? Also, can you suggest the most pleasurable condom brand (preferably one that doesn’t leave a poison taste on genitals)?

—Unwrapping

Dear Unwrapping,

I am so very sorry you’re dealing with this. I’m especially sorry that man put his ungloved penis back inside you. There’s been debate about whether that counts as sexual assault or should be illegal in a slightly different way, but it is never OK to penetrate someone without protection against their wishes. It’s also never OK to penetrate someone with protection against their wishes, just in case anyone is wondering. Frankly, I’m not thrilled with the begging types either.

For my part, I like to catch my partner’s penis between my upper and lower leg (nestled behind my knee) if it gets too close to my genitals during a romp before the condom goes on or after it comes off. It’s a bit cheeky, but does tend to keep them from risking fluid exchange. Hands work too, as do elbows, mouths, or just kicking the dude out of bed and telling him to come back when he can approach you with respect for your boundaries. I’m not sure how you can reinforce a boundary that is being ignored without killing the mood. I do think some moods are worth killing.

I can’t suggest the most pleasurable condom brand because I’m not you, so I’m not sure what works for your body. I’m sensitive to latex, so I tend to use SKYN (disclosure, I’ve worked with the company in an advertising capacity) or other non-latex but still FDA-approved condoms if the guy has a problem with my preference. Flavored condoms are a gagfest for me, but you might prefer them to the normal taste. Get some sampler packs and try some new ones out.

Dear How to Do It,

I might be the first woman in recorded history to say this, but I hate being called ‘“sexy.” It’s about 10 percent because it’s not a word I’d ever think of using to describe myself, thanks to some old, now mostly well-controlled body image issues, but 90 percent because I just have a squick about that word! I don’t like the way it sounds or even the way it looks written on the page. My (wonderful) boyfriend of four years will occasionally use it during sex, and it totally throws me off every time. I don’t know how to respond and usually just ignore it or mumble “thanks” and try to get back into the mood. On the flip side, apart from this he doesn’t often compliment my appearance—I could probably count the number of times he’s called me “cute,” “pretty,” or “beautiful” on one hand. I know it’s shallow, but it would mean a lot to me to hear that from him more often, although getting rid of “sexy” is probably more of a priority. Do I just learn to live with it? Say something? What would I say? “Please compliment me more but only use these specific words” feels both vain and nitpick-y.

—Not S***

Dear Not S***,

I don’t think you’re being vain or overly sensitive to semantics. Your squicks are your squicks, even if they’re someone else’s squees. It doesn’t matter if you’re the only woman in all of history who doesn’t want to be called sexy—you don’t want to be called sexy (although I’m certain you aren’t).

Now for the hard part: You’re going to need to talk with your boyfriend if you want his behavior to change. Your guy is calling you a word that doesn’t feel like a compliment, and until you tell him otherwise, he’s gonna keep thinking he’s complimenting you. Pick a time when the two of you can focus on each other, do what you can to make the environment conducive, and think about what you’re going to say beforehand. Maybe something like, “I love it when you express your appreciation of me by telling me I’m pretty, cute, or even beautiful, but the word ‘sexy’ just doesn’t work for me. It actually throws me out of the moment sometimes. Do you think you could try to use other words instead?”

The idea is to focus on the positive behavior you’d like to see instead of the thing you don’t like. I think you’ve got this.

Dear How to Do It,

I’m a 30-year-old cis woman. Nine months ago, I got divorced from the man I started dating in high school. We were together for 14 years and married for six; our relationship was emotionally and sexually over for about a year before we officially split. I’m feeling settled into my new life living alone for the first time ever, and I’m ready to start dating again. But my anxieties and insecurities have stopped me cold every time I consider setting up a dating profile online or flirting with a stranger. All the articles I’ve read about “how to successfully date online” or “how to get back out there” have been fluffy bits of nonsense, and I could really use some practical and useful advice.

I identify as bisexual or maybe pansexual, an identity that is purely hypothetical at this point. I really miss having sex and companionship with another person, but I feel really out of practice (and having had only one partner in my sexual history, I feel inexperienced as well). I’m not keen to jump into another monogamous long-term relationship right off the bat (if ever), but having a string of casual hookups doesn’t feel right for me either. It’s been over a decade since I’ve had to worry about STIs or negotiating birth control or even flirting with a new partner. I feel stuck in my fears, and I’m not really sure how to move past them and find what/who I want. Where do I start? I quite literally need someone to tell me How to Do It!

—HTDI

Dear HTDI,

First, let’s acknowledge that your feelings are reasonable. Dating is anxiety-inducing for lots of people, no matter their experience level, and it can even be scary—risks like STIs and varying degrees of assault are real, though manageable.

Remember there are lots of people in similar positions to yours. I’m in an oddly similar position myself—in the past, I tended to skip the dating process and jump directly into bed, and now I’m giving apps a try. We’re all bumbling around (or Hingeing, or Tindering), feeling kind of awkward and sending each other truly cringe-worthy opening lines. So you’re not alone. Give yourself permission to be shy, nervous, and maybe a little bit messy.

OkCupid might be a good starting place for you if you want to go the online route. It has a range of orientation descriptors, including pansexual, and a feature that even allows you to hide your profile from totally straight people. I haven’t used Feeld myself, but I’ve heard it skews pretty open/poly, so that might be another place worth checking out. Being an experienced poly person’s secondary partner sounds like a great fit for you at this exploratory stage.

One of the useful things about online dating is you can control the speed. You can always put your phone down or walk away from the computer if you’re feeling overwhelmed. It’s easy to unmatch with someone if they cross a boundary or do something that creeps you out.

When you do get there, remember sex is different with every new partner. You have to start basically from scratch every single time. Sure, you want to develop a larger toolbox, but you still have no idea which tool is the right one, much less how hard or rough to apply it or for how long. Allow yourself time to figure it out. Remember, you do have valuable intimacy experience that people who weren’t in a decade-plus long relationship don’t have.

So fill out a profile and show it to your friends. If that’s too much, ask them to help you draft it. Regardless, get some feedback on whether it represents you well from people you know and trust. When you do go on dates, send a screenshot of their profile and where you’re meeting to a friend. Make it a public place with lots of people around. Ask your friend to make sure you check in within a certain time. That will give you peace of mind. And listen to your gut. It’ll tell you if you’re moving too fast for yourself, and if that happens, it is completely OK to take a break.

Dear How to Do It,

I’m a 31-year-old cis woman. I feel like this is a bit ridiculous that I haven’t figured this out yet, but I don’t know how to describe my sexuality.

I’ve always described myself as straight, because my relationships have always been with men, and I presume they always will be. I don’t have romantic feelings toward women, nor do I actively seek out women for sex. But I have found women attractive and I have slept with women when the situation has naturally arisen, have really enjoyed it, and see myself always being enthusiastically open to it.

Because I don’t actively feel sexually attracted to women to the same extent I do with men. It’s always been very dependent on the individual woman and the situation, and I will probably never have a relationship with a woman. So it feels somewhat ridiculous and even appropriative to claim a sexuality other than straight. Even “queer” feels somewhat disingenuous, since I’ll always benefit from straight privilege. I’ve always been comfortable just saying I’m straight and then enjoying my occasional sexual experiences with women, but through my work and interests, I’m entering more spaces that actively address gender and sexuality and have a large LGBTQ population. I’m now frequently asked about my sexuality —and I’m feeling some pressure to more accurately represent it.

I’m also not 21 anymore, so calling myself straight but then sleeping with a woman elicits a stronger reaction from people than a permissive “whatever, it’s college!” attitude (which I deeply appreciated, to be honest). In fact, I’ve been accused of hiding behind the “straight” label to closet myself and benefit from straight privilege, and not “admitting” that I’m bi or queer. I understand why that person would think that, but that’s honestly not what I’ve been trying to do, nor is it how I feel. I’ve just always felt like I’m straight … with extracurriculars.

Do I need better language for this (and do you have any suggestions?) Or should I just continue calling myself straight, and privately enjoying my deviations?

—SWEC

Dear SWEC,

I mean, “straight with extracurriculars” is pretty spiffy, and a phrase you’re already using to describe yourself. You could also go with “Kinsey 1” or whatever number feels most accurate. My personal favorite, which I use to describe myself, is “bisexual but rarely bidate-ual.” I’m also fond of saying my fingernail length lets you know how hetero I’m feeling at the moment—the longer, the straighter. Occasionally bi, vaguely bi, and heteroflexible are all other ways you might describe yourself. Play around and see what fits. Make it your own.

Mostly, though, who are these people accusing you of hiding, being in the closet, and not admitting your orientation? That’s rude of them. Really rude. Yeah, visibility helps the movement. But—even today—not everyone is in a position to out themselves. Not everyone who is out wants to come out to everyone they meet, over and over and over. Unless they’re trying to have sex with you, or it’s a diversity in the workplace concern, I’m not sure why they even need to know. You get to decide for yourself who you explain your sexuality to. It’s your right to share or keep mum as you see fit. You don’t owe these people further insight into your inner world. Nor do you owe them an explanation as to why you don’t want to share.

Since you’re working and recreating in circles where active disclosure of identity is the norm, I think I get why you’d want to do so yourself. Just remember that it’s your identity to share as you see fit, and how you see fit. Labels like “bi” still don’t really tell us much about what the person in question finds attractive. Don’t let their need to know bog you down in attempts to find the most precise label.

More How to Do It

I live with my boyfriend of 10 years in a happy, committed relationship. My partner is a fantastic person and very considerate and giving in bed. So what’s the problem? I desperately want to have sex with other people. Every time we have sex or I masturbate, I think only of other people. Everywhere I go I get crushes: subway passengers, my bank teller, co-workers, the gamut. I can’t imagine a better partner in life for myself and I really don’t want to break up over this, but I also know that suggesting we open up the relationship would be devastating. I should have known this was going to be a problem before, because even in the beginning it wasn’t his physical appearance that attracted me to him, but we fell in love anyway and have now built a life together. How do I manage this? It’s not going away, and it feels like I’m already cheating.