How to Do It

My Boyfriend Has Asked for a “Hall Pass”—but Only for Him

A man trying to talk to a woman.
Photo illustration by Slate. Photo by dima_sidelnikov/iStock/Getty Images Plus.

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,

My boyfriend of two and a half years has been having dilemmas that he has just recently brought to my attention. He brought up the idea of a hall pass with me. Not for me, but for him. He says that he has been feeling less attracted to me lately, and he fears that he won’t ever be able to gain it back. He thinks that it’s because he has had a lack of sexual experience because I am his first and only girlfriend. I asked him what specifically about me he isn’t attracted to, but he said he can’t pinpoint a particular thing because he doesn’t know, it’s just been happening over time. He said that he often has sexual thoughts of other women, which make him feel guilty.

I do, however, understand that guy’s brains are wired differently than women. I understand on one side that he may feel like he doesn’t know if he is missing anything, but at the same time, I feel like if I say “no” to the hall pass that I’m just putting a death sentence on my relationship. He said he has easy days and hard days, but they have been getting harder, and he is going to start therapy. He also said that if I were to say no to a hall pass, he would get over it and just continue to work on it, but that doesn’t seem to have been working very well because … well, here we are. I think I would consider a hall pass depending on the circumstances. He was understanding of the fact that if I did decide to consider it, it would be on my terms, and he was willing to follow the terms I place. He stresses to me all the time how much he loves me, but sometimes I worry that he just doesn’t want to let go of what he has while still being able to mess around with who he wants. I don’t know if this is going to break my relationship or make it stronger. Also, if I were to agree to the hall pass, what things do you think I should consider as far as how a hall pass would work? What “terms” should I consider?


Dear Overwhelmed, 

Your boyfriend should have presented this issue in a more sensitive manner. Telling you that he’s feeling less attracted to you certainly gets right to the point, but a little tact would go a long way here. Maybe your recap is losing some finesse in translation, maybe you’re too emotionally mature to make a big deal about his brusqueness, or maybe, if the situation played out as you presented it, it speaks to a relationship dynamic in which his feelings are prioritized over yours. Hard to say, but his willingness to abandon his pursuit of an open relationship upon your refusal does speak to an egalitarian potential.

Waning desire in long term relationships is extremely common—our perennial favorite, Esther Perel’s Mating in Captivity, covers this topic in detail, and it is something that you should read, because it offers many suggestions for reigniting eroticism in a monogamous relationship. If you do decide to open things up, you should consider your comfort level. This sort of arrangement is not likely to work unless you’re both on board. When there’s a disparity in willingness, it can sometimes cause arguments after the fact. And then, what was once peacefully agreed upon becomes contentious, as if cheating took place, even though the entire reason to negotiate these things openly and in advance is to snuff out the idea that sex with someone else constitutes cheating. Different couples have different rules: Some put limits on the amount of times they’re allowed to have sex with a person outside of the relationship, others put limits on the number of people they’re allowed to have sex with. Some have open relationships in which sex with others is only allowed when one person in the relationship is out of town. Some people prefer their partners tell them nothing about their extracurricular dabbling; some want to hear everything. One potentially nice thing about this stuff is that there is no unilateral doctrine for all open relationships—you get to set your own terms based on your needs. What are you OK with? If the answer is absolutely nothing or something close to that, an open relationship probably isn’t for you.

You mentioned that he suggested this pass for him. How about you? Are you interested at all? If so, it might make things easier for both of you if you too experiment with others. If not, you should at least be given the option. Keep a close eye on your man’s generosity-to-selfish ratio—this isn’t something to brush off because you believe his brain is “wired differently.” He could be cluing you in on the future of your relationship before you even give him the opportunity to ethically stray.

Dear How to Do It,

I’m a man in my 30s, and I’ve been shaving my balls and generally around my shaft and taint for about 10 years. Relatively recently, shaving the area to the left of my balls and shaft has been irritating and even caused very light bleeding. It feels like I’m shaving against the grain, but I’ve been shaving this way for 10 years! I didn’t really think much of it at first, but it’s been going on for at least a month or two now. Maybe even since quarantine started in March or April?

Last week, I swapped in a new razor cartridge thinking maybe it had just been a while or the last cartridge was a dud, but it’s just as bad with the new one. As far as I know, nothing else has really changed. I shave in the shower twice per week and have used the same razor handle with the same style cartridges for about 10 years. The cartridges have four blades and a little green moisturizer strip thing. I’ve never used shaving cream for this (probably because when I started shaving down there, I was worried shaving cream would make it harder to see what I was doing). I don’t see anything that looks like an ingrown hair or anything else that looks wrong or out of the ordinary. I don’t think it could be connected to an STD because (a) I’ve been married and living with the same monogamous partner for 10 years and (b) quarantine.

I may have opened a new body wash around the time this started, but it’s just like a generic moisturizing body wash. I always just buy whatever is the cheapest and that also looks like a moisturizer and isn’t specifically marketed to guys (sorry @Axe, but you’re gross and I’m not 12). To be clear, I do wash my dick and balls with this. That’s the only thing I can think of that might be different about my shower routine now. Any ideas? Is my body just telling me it’s time to stop shaving? Besides the new cartridge, I have also tried shaving different directions to no avail.

—Bad at Puns

Dear Bad at Puns,

The clear answer to this is: Go see a dermatologist. But to do my small part in socializing U.S. healthcare, I shared your question with my dermatologist on a recent visit. His response? See a dermatologist. He told me there could be a number of reasons why such a rash would suddenly present, including dermatitis and STDs—he’s had patients certain that they were STD-free that, what do you know, turned out not to be upon examination. (Some can lie dormant forever!) Additionally, the angle of the razor could be a factor—the slightest change in manufacturing might cause such a disruption.

One thing that my doctor and I didn’t talk about because we didn’t have to, as he drilled it into my head years ago, is how important it is to use quality body wash and moisturizers. Your best bet is to go color and fragrance free. If you can afford it, start using Cetaphil or CeraVe, which are gentle and effective. It seems that you’ve targeted a prime suspect here—a cheap body wash that you’re also relying on to moisturize (???)—and so changing that should be your first step. Moisturizing with an actual moisturizer should follow soon after.

Dear How to Do It,

I am 28 years old and have been dating my girlfriend for a little more than a year. We have a great relationship, and she is truly the love of my life. We have sex almost every day when we are together, and we both really enjoy it. She also gives me blowjobs and hand jobs quite often. Although my girlfriend enjoys sex, she struggles to come during traditional intercourse; however, I am able to easily make her orgasm through other means, which I enjoy doing. She says she is satisfied completely with our sex life and so am I.

The issue that I have is that I was a late bloomer—I only lost my virginity a couple of years ago (I had high anxiety around women), and because of consistent masturbation over the past 15 years, I initially had a hard time orgasming during sex. I started masturbating with a Fleshlight and that seems to help to some degree as now I am able to orgasm during sex, but only consistently when she lays on her stomach and I’m on top. If we do missionary, spooning, or anything with her on top, I rarely can come, so I either need her to finish me off via a handjob or we switch to the position where I can cum. She says that she doesn’t mind this at all and that my favorite position is also her favorite, but I’m worried that only being able to orgasm consistently from this one position will be an issue further down the road. Am I overreacting or is this a big deal?

—I Want It That Way

Dear I Want It That Way,

This is not a big deal. You both “really enjoy” and are “satisfied completely” with your sex life. You have overcome what only the narrowest way of thinking about sex would consider to be obstacles—that thinking assumes that everyone should be able to orgasm from everything. Real life begs to differ. All the time, we hear from people who have tried everything and yet still can’t manage to come. You’re both managing and you’re loving it.

There’s little use staying hung up on something you’re already succeeding at, but your overachieving spirit suggests that you may regardless. If that’s the case, you can attempt to experiment with your masturbation habits and techniques to see if that affects your sex life or overall sensitivity. I’m not nearly as convinced as you are that your initial difficulty in orgasming had to do with your masturbation (you mention anxiety in the very same sentence!), but I trust your reporting that varying stimulation has seemed to lead you to an easier time coming during sex. Try going a week without any masturbation and see if that affects things. Try changing your grip or even the hand that you use to see if you can acclimate to varying sensations. Play around with your playing around. It’s fun!

Dear How to Do It,

I am a 49-year-old gay man who has been a barebacking top for pretty much the last 30 years. In fact, I hated bottoming. That pretty much changed when I recently discovered chem sex (which I do responsibly only one weekend a month). Now, I enjoy topping and bottoming equally.

Here is my compounded problem: 1) Lately I prefer to get messed up alone and watch hot porn and penetrate myself with my newly acquired toy collection. Otherwise, I’d get invited to a group of five or six guys where we meet up around on a Friday afternoon and finish on a Sunday morning. I’m finding that I’m having more fun by myself than with other guys. 2) When I do desire other people, I’m getting turned on by trans porn and fantasize about taking it from a trans girl with a big dick as well as me having sex with a hot trans guy. I’m not saying that I want to make sex with transgender people a new and permanent staple to my sex life, but I do want to try it. Before COVID-19, I went to a trans club and a real hot gal approached me. But I let my being bashful get in the way. I was too embarrassed to ask her if she partied, or played bareback. I did not want her to think I was being disrespectful. Is it normal for me to want to do this at least once? How should I generate confidence and approach it?


Dear ShyGuy69,

I’m going to decline advising you on your drug use, as you did not solicit it. Judging you would not serve anyone, and change in that area would have to come from within anyway. That said, I do feel like a pinball that just racked up hundreds of thousands of points while dinging around your sexuality as it’s laid out in your mind. I’m practically dizzy from reading all that. Whew. I’ll have what he’s having: A really long rest!

Is it normal for you to want to have sex with a hot trans person? Yes, that seems “normal” to me. If we erected a lab and I donned a white jacket and you laid down on my table, I doubt we’d get to the bottom of whether or not the drugs somehow manifested a new sexual interest of yours or unlocked one that was already lying dormant and is now awakened. I’m not sure it matters, either. You like what you like. Just please treat trans people as you would any people, with full cognizance that they are, in fact, people and not your sex toys. Keep this in the forefront of your mind and go out of your way to be kind.

As to how to generate confidence … the drugs aren’t enough? Are they even doing their job then? Confidence is the sort of thing that you can project even if you don’t actually possess it and no one’s the wiser. Like rhinestones to a 4-year-old, it’s just that shine, even if your article isn’t genuine. Fake it till you make it.

More How to Do It

My husband and I married young and have been together for 15 years. We have two small children together. I’ve never been intimate with another man. (He had one partner before me.) The sex has always been … fine. He is very into performing oral—although I think his enthusiasm outstrips his skill—but I prefer penetration or manual stimulation to get off. He’s average size and has never been a marathon man. My tastes have started to run less vanilla, and all I want lately is really rough sex with a big, hard dick operated by someone who really knows how to use it. I’ve recently started chatting online with a sexy, well-endowed man in a similar marriage situation, and that initially very innocent friendship has gotten increasingly inappropriate.