How to Do It is Slate’s sex advice column.Have a question? Send it anonymously!
Dear How to Do It,
I’m a woman who’s been with this guy three times. We hit it off well, and the making out is always fun. He’s pretty easy to reach for a last-minute “you up?” text, which is a plus. But there’s one hitch—he struggles to maintain an erection.
During our first two encounters, I was fine just fooling around and even gave him oral, which, oddly enough, got him hard when penetration didn’t work. Last time, though, I think I might’ve rolled my eyes or shown some frustration when he couldn’t maintain it again, and still expected me to give him oral. Awkwardly, he seemed a bit hurt by my annoyance, but I went ahead anyway. The kicker? He’s never reciprocated or gotten me off in any way! Is it time for a talk about this, or should I just walk away?
—Never My Turn
Dear Never My Turn,
It’s possible that talking about reciprocation could lead to a positive shift in his behavior. However, he might reveal a lack of interest in prioritizing your pleasure. Bringing up the subject opens the door to many outcomes. Keep in mind that some guys have very limited sexual education and might not even be aware that women can feel pleasure during sex, which could offer a chance for growth.
If you find out he’s being selfish, it’s worth having that conversation. Depending on how much you actually like him, you might decide to take the time to help him with whatever is causing his anxiety about pleasure. If you’re interested in a relationship that goes beyond a hookup, this kind of emotional support could be beneficial. You might even learn something valuable about your needs for the future.
But then again, I’m not sure how well you connect beyond physical attraction or what personal anxieties you may have. Some people may feel uncomfortable confronting someone about a lack of reciprocation. Are the potential upsides of the conversation worth the hassle and risks involved?
Either way, remember that you owe him nothing outside of basic respect; if you decide it’s not going to work, a simple “This isn’t for me” is more than sufficient.
Dear How to Do It,
I’m seeking advice on dating with a health issue. I’m a 54-year-old man who ended a long marriage just before the pandemic hit, losing not only the momentum to meet anyone new but also the intimacy that came with that relationship. To top it off, I deal with chronic migraines, which leave me drained and sensitive to various stimuli. This impacted my marriage and makes me cautious about dating again.
I’d prefer to be upfront about wanting a more casual arrangement for now, as I’m not seeking a caretaker nor rushing into another long-term commitment. I want to avoid disappointing someone due to my unpredictability caused by illness. I crave human connection but worry how to present myself online—without coming off as a sad, divorced guy trying to get back out there. I’d also rather not put any potential partner on edge with my sensory needs. Should I be completely open up front? And what apps are best for someone like me in their 50s?
—Willing But Alternatively Able
Dear Willing But Alternatively Able,
It seems you’re someone who likes to analyze and think things through. You might want to channel that focus into understanding what triggers your migraines and how to manage them better. This knowledge can help you communicate more effectively with others, especially regarding your limitations.
Being able to articulate what might lead to a last-minute cancellation—for example, weather changes—is helpful for potential dates. It allows them to decide whether they want to proceed or wait for a time when you’ll be less likely to have to cancel. Creating a list of acceptable meeting spots that work for you will help ease both you and your potential partner into the dating world. Consider quieter venues that align with your interests, especially as socializing norms have shifted since the pandemic.
Additionally, clarifying what “casual but ongoing” means for you can set clear expectations. Sometimes, when we focus too much on what we don’t want, we create an overall negative impression. It’s also crucial to evaluate whether you’re carrying emotional baggage from your divorce, as this might complicate your search for connection. After all, hoping a casual relationship will mend old wounds could lead to unmet expectations.
Dear How to Do It,
I’ve been with my husband for over a decade, and while we still manage to have sex regularly, I’m beginning to feel I’m not doing enough to please him. We don’t engage in much oral sex, and I mostly focus on my own pleasure. He only allows me to take charge sometimes, usually after I’ve orgasmed. I’d like to contribute more to his pleasure, but I’m not sure how to do that or what to change about our dynamic.
—Pillow Princess
Dear Pillow Princess,
Your concerns are worth exploring. You’ve indicated that your husband hasn’t expressed dissatisfaction, so it might be wise to ask him what he enjoys or if he’d like to see any changes. There are various reasons why he might prefer to be the one in control, from societal norms to genuinely wanting to ensure your pleasure.
If you have specific desires for your intimate life, communicate those gently and ensure you prioritize consent. However, if your primary concern revolves around feeling inactive, maybe just initiating an open dialogue could be the solution. You might both be stressed about the other’s satisfaction, and by discussing it, you can address any misconceptions. Sometimes, just being honest about your feelings lays the groundwork for positive change.
In the meantime, remember that many couples enjoy simple and warm intimacy, and it doesn’t need to be overly dramatic to be fulfilling. Books and resources exploring satisfying relationships could give you fresh insights and reassure you about your current situation.
—Jessica
