When I took my date’s pants off, I was in for a shock. I’m not sure where to go from here.

How to Do It is Slate’s sex advice column. Have a question? Send it to Jessica and Rich here. It’s anonymous!

Dear How to Do It, 

I recently started casually online dating after leaving an abusive marriage, and it’s been going great! There have been lots of nice guys, and we have had some sexy fun. That said, I’ve run into a weird situation that I’m almost certainly overthinking but am baffled by.

I used to work in adult retail in my early 20s and am a very empathetic and sex positive person, all of which is information I share either before meeting or on the first date. I went on a first date last night with a great, interesting, funny guy that I got along very well with, who told me after dinner that he has a medical condition that causes incredibly painful erections and, because of this, has had difficulty with intercourse (and subsequently, online dating). Being the curious and empathetic person I am, I asked if he wanted to take me back to my place, and we had some really incredible foreplay.

When his pants came off, I found that his penis was bent upwards in a U shape with his head pointing back towards his stomach. I saw a decent assortment of penises in my porn store days and am good at keeping my face neutral when I see something new at this point (with my apologies to the guy with the micropenis I slept with when I was 19), so I modified my usual blowjob routine to work with what I had and we were able to have relatively satisfying PIV intercourse, that he initiated. I have two questions.

How can I balance wanting to make sure he’s not in pain and is enjoying things as we try stuff out with not completely killing the mood every time we switch to something new, especially since there isn’t a blanket answer to what will or won’t be painful on a given encounter? He has the type of personality where I’m concerned he might not vocalize that he’s in pain, so I don’t feel weird about the whole thing, but I don’t want to be causing him discomfort. My other question, and I feel bad for saying this, is… I love a good dick. So much. And after getting out of a bad marriage with bad sex, I was really looking forward to exploring the world of dicks for a while. I’ve been open with him about the fact that I’m just casually dating at this point, so I’m not especially concerned that I’m leading him on, but am I a total … dick if I come to realize that it’s a deal-breaker for me? And if it is, how do I say or not say that so that I don’t make this sweet man feel any more awkward about his condition?

—Getting Bent

Dear Getting Bent,

Talk to him about how, in general, you need to feel like your sexual partners will let you know if they’re in discomfort. Make it clear that this is something important to you, regardless of the individual’s body or any rare differences, but, you know, without emphasizing the latter excessively. Ask him whether he feels like he’s able to do that. If he’s unsure, find out what might be holding him back from doing so. If you still aren’t comfortable assuming he’ll say something in the moment, that’s a cue to move along.

You almost certainly already have some awareness of his facial expressions, body language, and vocalizations during sex. During this initial phase, focus a little extra on understanding what he looks and sounds like when he’s having a good time, and when he’s experiencing discomfort, until you feel like you have a pretty good grasp of his individual lexicon. If you’re inclined to notice tactile cues, such as certain parts of his body developing tension, make note of those as well.

From there, it’s the same reliance on the twin pillars of “I trust this person to usually notice and speak up if they’re uncomfortable” and “I trust myself to usually notice if their signs of pleasure stop or signs of pain start” that we tend to have in sexual encounters. Even together, the two aren’t completely foolproof. But they are the best we can do without the ability to read minds.

As for whether it’s a dick move to decide that the sex isn’t working for you in a way that your partner can’t do anything about, broadly speaking, I’d say no. No more than it’s a dick move to decide you’re unwilling to relocate to a different city, live a significantly different type of lifestyle, or date people of genders outside your sexual orientation. What would be a dick move, though, is focusing entirely on people’s dicks as a metric of whether you’re interested in continuing to see them. I suspect that when you’re considering your dates, you are factoring in many other features. So, as much as this man’s member is quite the outlier, keep an eye on the bigger picture.

If you do decide to end the relationship, remember that no matter how gentle you are, you can’t control how he reacts. There’s one possible world where you let him know that you’re no longer interested in seeing each other, and he’s relieved because he’s been trying to figure out a way to break things off with you. There’s another where you end the relationship over, say, political views, and he still makes it out to be a rejection over his dick. One thing you can do at this stage, while you’re waiting to find out what your feelings are toward him (and his anatomy), is resist any temptation to see him every other day or stay in constant contact—keep things as casual as you’ve told him they’re going to be.

Dear How to Do It, 

As a 21-year-old woman who is a virgin, I know I’m late to sex. I’d ideally like to start having some—but be it because of my generation’s sex recession, my own shyness, or the complete absence of dating culture, the opportunity has never really presented itself. I never dated in high school (I wasn’t interested, and was too focused on getting into college to have a relationship), and by the time I got to college, I just kind of assumed it would happen on its own. But in truth, there isn’t much of a culture of hookups or dating at my college, as it’s very small and competitive. Everyone is pretty awkward all around. I’ve had a longer-term relationship with a guy before, but he was religious and wanted to wait until marriage, so nothing ever happened (we broke up for reasons unrelated to sex). Hinge led to a handful of OK first dates, and Tinder led to six cancellations and two honestly terrible in-person encounters. I’ve since deleted the apps to focus on school and just to get off my phone. At this point, I’m not even sure if I’m into men, or if I might lean more lesbian.

I felt like my college years were hyped up as a time of casual sex, exploration, and fun. I genuinely don’t know what I’m doing wrong. I’m decently attractive, funny, and have plenty of friends at school and work; in all other ways but this, I have my life together. My parents and relatives frequently question why I’m not in a relationship.

Is there any way forward in this situation? I’m not looking for a long-term relationship right now, but should I try for one just to see where things go? Redownload the apps, or try a different platform? Or just surrender and accept that my virginity doesn’t really matter to anyone but me?

—Hookup Hungup

Dear Hookup,

I’m guessing that part of your perception of college as a time of casual sex, exploration, and fun comes from the media you were exposed to growing up—be that social media or television and film. But both memes and movies tend to distort reality. A whole bunch of people in previous generations got through college and then found themselves feeling they’d missed out on a big bacchanal. Also, a lot of Millennial hook-up culture took place in a context of large quantities of alcohol and substances, which has a way of removing inhibitions. Given the ways that inebriation clouds consent, it’s for the best that this former fad has faded.

Another cultural institution that seems to be transforming is the dating app. Where 15 to 20 years ago, dating apps often felt like they were opening up a whole world of romantic and sexual partners we might be more likely to share interests and desires with, many people now describe them with a lot of frustration, often lamenting that they’re full of scammers and profiles that seem to be bots. Mostly, though, lots of people—including your peers, and maybe even some of your classmates—are having the same desire you describe of wanting to get off their devices.

So get out there and meet people. Join a club, bring any schoolwork that can be done in a public space to a cafe or similar, and go out with friends. Do whatever you can to put yourself in situations where you might socialize. Keep an open mind about whether the people you’re meeting will fit in your life at all, and especially what form being in your life might take. Maybe you make some new friends, you find someone to hook up with, or you do find someone you want to develop something longer-term and romantic with (and who wants the same with you). Yes, there will likely be some awkward moments. Those uncomfortable moments often decrease with experience and practice. Most of your cohort are probably in a similar position—they all went through the upheaval of COVID lockdowns in their high school years, too, and you’re all part of the same generation that is reportedly going through a “sex recession” (however actually accurate that is). Even if sparks aren’t flying, you can support each other through the experiences you’re having and longings you’re hoping to fulfill.

Your virginity likely won’t matter to most people nearly as much as it matters to you—although every once in a while someone does make a big deal of it in one way or another—but it matters to you. Build a support network that will hopefully help you through that, and you might meet someone whose desires align with yours along the way.

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Dear How to Do It, 

My lovely wife and I (cis female and male, both 40 years old) have maintained very active and fulfilling sex for over a decade. Over the past several years, we’ve slowly incorporated various toys into our sex life to great success. Our most prized possessions are a few large dildos that have become part of our standard repertoire. My wife loves being stretched out, and I love pleasuring her with them. It’s a win-win, and we have a lot of fun.

Over the past year or two, however, my wife has been getting sporadic UTIs and yeast infections, and they’ve always come on the heels of a session with the big boys. We always do our best to keep everything sanitized, and we always make sure that the toys are cleaned thoroughly with anti-bacterial soap after each use and stored separately in their own bags. The dildos are never used for anything other than vaginal insertion.

A few months ago, we decided to start putting condoms over the dildos to prevent any infection. (We still maintain the old cleaning routine, too. That hasn’t changed.) Things were going great until our last session, when my wife got yet another yeast infection after an evening with her largest toy wrapped up in a condom. We are both feeling frustrated and stumped. We love playing with the toys but it’s crushing for me to see her in discomfort and pain the day after a fun evening. Is this just a normal risk of using large toys? Are there better precautions that we could be taking? Is there something we’re missing?

—Not All Fun and Games

Dear Not All Fun and Games,

It’s worth your wife making a trip to her gynecologist, explaining the situation, and asking for some extra testing to confirm that what she’s experiencing really is recurring UTIs and yeast infections. So many different factors can throw off a vaginal microbiome, and more than one can result in the kind of discharge that looks like a yeast infection or the symptoms that read as a UTI, but it could be something else entirely. She should call the office, explain the situation briefly, and ask when it is best to come in—sometimes the doctor needs to see the issue when it’s active, and sometimes they want certain tests run before the appointment.

That said, yes, really intense sex (whether we’re talking about duration, degree of vigor, or girth of a penetrating object) can, without other factors, cause a big, painful mess. Since both of you enjoy this practice, it might be that big toys need to be a special occasion activity and reserved for times when she’ll be able to recover in comfort afterward. The good news is that there’s a whole wild world of sexual practices outside of big toys, and a significant chance that you’ll be able to find something else you both love just as much to fold into your repertoire.

—Jessica

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