DEAR DR. NERDLOVE: I’m a 35 year old man with an annoying problem: I’m having a hard time orgasming during partnered sex. This is a relatively new thing for me. Before now, I’ve been pretty standard in terms of my sexual response via penetration. I hadn’t been a two pump chump but I also have never been able to go for long periods of time either, which has always been fine with me and my partners. However, with the last few sexual encounters I’ve had, it’s gone one of two ways. Either I would get somewhat close to orgasming (I could feel things starting to build) but could never get all the way there or I just never even got to the build-up and was just thrusting away until either it was getting uncomfortable for my partners or I just gave up entirely and finished myself off later. 

This has been exclusively an issue during partnered PIV sex. I’ve never been able to get off from oral, even though I enjoy it) and I can get myself off just fine when it’s just me. I don’t know if it’s the condoms (I have HSV-2, so they’re non-negotiable) or what, but it’s getting frustrating to me. My various partners have been very kind about it, but I can tell that they’re frustrated too. 

What do I do, Doc? 

Don’t Want No Thirty One Minute Man  

DEAR DON’T WANT NO THIRTY ONE MINUTE MAN: This is a condition that’s called anorgasmia, DWNTOMM, and trying to diagnose the cause is usually a process of elimination. Since this is a relatively recent phenomena for you, the first thing I would suggest is to look at what may have changed, recently.

One of the first things I would do is check on any new medications you may have started, especially if you’ve started taking an SSRI or similar drug, or if you’ve started taking medication for conditions like high blood pressure or prescription painkillers. There are a number of drugs that can make it harder for men (and people with prostates and penises) to reach orgasm during sex.

Similarly, I’d suggest to look at whether you were using the same condoms as usual; if you’re used to a particular brand with a specific thickness, texture or lubrication, then changing that might make a difference in terms of sensitivity and sensation which could delay your orgasm past the point where you or your partner would be comfortable continuing. The same with any supplemental lubricants you might be using – it’s possible that you may have been using enough that you reduced the amount of friction you needed to achieve orgasm.

There’s also a question as to whether you’ve been drinking or using other intoxicants(cannabis – including CBD or Delta-8/9 products – and cocaine in particular). “Whiskey dick” is a very well-known phenomena, especially as we get older and our tolerance for booze and drugs changes. Limiting the amount you drink, smoke or otherwise consume can help you avoid similar frustrations in the future.

The next thing I would suggest is to ask how aroused you may have been with your partners, how attracted to them you were. I’d also recommend taking a look at whether there’ve been any issues in your life that’ve been affecting you mentally or emotionally. Stress can affect not just your libido, but also your sexual response, making it harder for you to get off. Or if you’ve had issues with your self-image – something that may make you feel less attractive or sexually desirable – then that may be a factor. The whole “the brain is your biggest sexual organ” may be a cliché, but it’s a cliché for a reason, and if you’re not feeling yourself, it can make things harder for you.

Er… as it were. 

I’d also recommend that you talk to a urologist. While 35 is fairly young for prostate problems, it is a possibility and can frequently cause issues with orgasm. They may recommend a blood draw to test for any issues with Little Man ‘Tate; if they do, then do your best to avoid orgasm or vigorous exercise (especially bike riding) for 48 hours in order to get an accurate read on your PSA count.

Now the one thing that you said that pinged for me was that you can still get off through masturbation. One thing you may want to pay attention to is how you’re masturbating: are you using your hand, an insertion toy or something a little more outré like the ol’ JD Vance special?

(No, seriously; some folks discover masturbation by rubbing themselves against a pillow or sticking their penis in between cushions or between the mattress and box spring.)

If you’re using your hand – or using something that has a strong texture or pressure, like the aforementioned cushions – you might be using a level of pressure, texture or friction that the human body can’t reproduce. This is what’s known as an “idiosyncratic masturbation technique” or more colloquially known as “death grip syndrome”, and that makes it a lot more difficult to get off with a partner. This might be something that you may not have realized you were doing at first: gripping a little harder if you were having a harder time getting off or sitting in a way that was putting pressure on your prostate that you aren’t doing during partnered sex.

If you’re gripping it and ripping it, then you’re training your penis to respond to that particular level of pressure, and it’s not going to be as responsive to the less intense pressure of a vagina, mouth or anus. The key then is to essentially retrain your junk – using the barest amount of pressure to masturbate and accepting that if you don’t get off, you don’t get off until you do respond to something more attainable by a human body. If you aren’t sure of your ability to keep yourself from grabbing a little harder when you’re trying to get over the falls, you may want to look into a masturbation sleeve like a Fleshlight or a Tenga Flip. This can help retrain your orgasmic response to something that you will encounter with another person.

Now, assuming that you have a clean bill of health and you’ve eliminated other possibilities, one thing you may want to do is adjust how you’re having sex with your partners. For one, you may want to consider adding a few drops of lube to the inside of the condom, to help add a little sensation and motion. And I do mean “drops”; you don’t want so much that you risk the condom sliding off. You may also want to consider a little prostate play when you’re almost-but-not-quite there. Even a little pressure between your scrotum and your anus can help nudge you over as well as make the orgasm a lot more intense.

Alternatively, if penetration isn’t going to get you there, you could always let your partner jerk you off to finish instead of doing it yourself later. It can even be kind of hot with a little dirty talk or a little of a dom/sub dynamic.

Regardless, however, I’d still recommend talking to your doctor, just in case. This is one of those areas where it’s better safe than sorry, especially if it turns out that there’s something that you need to be paying attention to.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: How do you date if your depression isn’t fixable?

I’m 49 and when I say I have tried everything in forty years I don’t mean “ha ha I’ve tried everything”, I mean I have literally tried everything…dozens of different anti-depressants, five psychiatrists, CBT (a full IRL course held by one of the top shrinks in the province), exercise, magic mushrooms, and on and on…the only things left to try are either super illegal or scary as hell (electro shock therapy).

I go to 6-10 events a month where meeting people is either a focus or a part of the experience (i.e. pickleball, bar trivia etc..etc..) and while I have made some friends, I haven’t even come close to landing a date let alone ending my 7 years of celibacy. I try very hard to have positive energy but I am not, nor capable of being, the happy go lucky people magnet I’d love to be.

I try to be my authentic self and while I know it’s entirely possible to be unlucky for long stretches of time, I worry that I can’t fix one of the core problems that must surely be part of the problem.

I don’t know what else to try. I am getting to the point where I feel worn down and mostly just want to stay home.

Down Down In Brain Goblin Town

DEAR DOWN DOWN IN BRAIN GOBLIN TOWN: Depression is a monster. And worse, it’s a monster that doesn’t even necessarily look the way you expect. For some, it’s being down in the dumps – the classic “feeling sad, lonely and blue, no matter what”. For others it’s simply feeling worthless or that everything is pointless and hell, sometimes it’s not feeling anything at all; just an ever-present gray numbness that saps the energy, life and vitality out of everything. In some ways, that can be the worst – imagine how it would feel if everything, including your formerly favorite foods, had no taste or smell, only texture. How quickly would that start to feel like an inescapable hell?

I’m truly sorry that your depression is so resistant to treatment. I will say that electroconvulsive therapy (the “electro-shock” you mention) only sounds scary. I know it conjures up images of One Flew Over The Cuckoo’s Nest or horror scenes set in haunted asylums, but in practice it’s nothing of the sort. It’s a very gentle procedure that’s done under a muscle relaxant and general anesthesia. You don’t arc or flop around, the lights don’t flicker and you’re not coming out of it drooling and insensate. In fact, the only physical indication is a slight tensing of the fingers and toes. It has a very strong track record of actually helping with symptoms of treatment-resistant depression and working very quickly, so it may be worth talking with your doctors about the option. I’d say find out more, if only so that you don’t have the terrifying images of what the therapy actually looks like.

But I’m not here to tell you how to cure your depression, I’m here to tell you how to try to live with it. I’m stressing live with it, because that’s the critical part. I think you’re trying to live like you don’t experience it and that’s a part of the problem. Sometimes the only thing to do is to learn to work with and adapt around things, rather than trying to force it away, and that only serves to make things harder. And honestly, there are only two things that I would tell you.

The first is that having depression doesn’t mean that you can’t be loved or don’t deserve to be, nor do you need to not have depression in order to find love. Things can be difficult – it’s hard to feel good about a relationship when nothing feels good – but that’s a challenge, not an impossibility. If you have friends and you’re capable of maintaining those friendships, then you’re capable of finding love. It means finding the right people, which will be a challenge, and it means working within your limits, which can be maddening. But a challenge is different than “impossible”. 

At the risk of making a cheesy, Tumblr-esque comparison, I’d suggest that maybe you should consider the case of Eeyore. Yes, Eeyore from Winnie The Pooh. And yes, I’ll be the first to say that I’ve mentioned that Eeyore isn’t exactly considered a sex-symbol. But this isn’t about being a sex-symbol. This is about looking at Eeyore and his friends. Because Eeyore, for all that he’s gloomy and always down… he’s still making an effort. He’s there with his friends, taking part as best as he can. He may not be the most enthusiastic, he may not be the most energetic or taking the lead in all the fun and games, he’s still there. He’s still showing up. He’s still participating both to the best of his ability, but also to the best of his capacity.

Those three things are important. Showing up, even when you’re dragging ass and not necessarily feeling it, helps you avoid one of the more pernicious parts of depression: the isolation. It’s very easy to slide into a sort of self-imposed solitary confinement when the depression is especially dire, and once you start, it gets harder and harder to get back out again. Hiding yourself away from the world also hides you away from the goodthings in life, things that boost you and carry you a little further, even if you’re not necessarily feeling it at the time. When you’re isolating yourself, the loneliness and the solitude serve to enhance those feelings (or the lack thereof), let them settle and become the status quo. The longer you stay isolated and lonely, the stronger the depression gets, and the harder it becomes to motivate yourself to push through it.

Trust me: I have been there and done that and I can tell you that the worst times with my depression were always because I had isolated myself from everyone.

But participating is also important because it reminds you that you’re alive. It reminds you that you have choices and options and agency; these are the things that keep you in contact with your friends and loved ones – the people who love you, care about you and have your back. These are some of the people who give you the strength and the desire to push through that fog, to go stay connected with others, even when it feels pointless or like there’s no reason for it. It may not change your mood or lift the numbness that surrounds you, but it does remind you that life is for living, even when it doesn’t feel like it.

And participating to the best of your capacity reminds you that you don’t have to exhaust yourself or break yourself into pieces to be considered part of the group or to maintain your friendships. Your energy levels are low to begin with and depleting them past a certain point can make the depression feel worse. Learning how to manage your energy – when to expend it, when to husband it, how to recover it and what kinds of recovery you’ll need – are an important part of keeping yourself going and not letting everything fall apart.

But the other important thing about Eeyore are his friends. Specifically: they’re not trying to fix him and they’re not demanding that he put on a happy face when he can’t feel happy because it brings them down. They’re just glad he’s there and they want him to know they’re glad. They want him to know that he’s a part of the group and that his showing up means a lot to them.

This is what you want in friends and in potential lovers; you want people who understand that this isn’t something that they need to “cure” or “fix” for you, nor do you want people who think that your depression is something that brings them down. You want folks who are willing to accept you, who will meet you where you are and understand that just because you may not have the full capacity that they do, that doesn’t make you lesser or worth less. It just means that you don’t have the spoons that they do.

The second thing I will tell you is very simple but also very difficult: don’t give up. I don’t just mean on life – but no, seriously, don’t – I mean on not giving up on living. On trying. On continuing to put one foot in front of another, dragging yourself out and finding reasons to go out, to participate in your life beyond the bare minimum and to continue doing your best to build and maintain those relationships.

It’s easy to say and in concept it’s simple to do. But the execution of it is hard, especially when it feels pointless. But it’s that feeling of pointlessness that makes it all the more important. Part of the problem with depression is that depression turns you into a weird sort of shark; there’s nothing you want more than to stop moving, to lay down and be still, but when you stop moving you quit living. The longer you stop, the harder it becomes to start again. And once that sets in… well, that’s when the depression starts to be at its worst and becomes ever harder to break out of.

Now this doesn’t mean going balls to the wall, beating down life’s doors like you’re demanding the money it owes you. Sometimes it means just gritting your teeth and deciding that you’ve got a job to do and you’re going to do it because you’re a goddamn professional. And then you let that sheer determination – or spite, for that matter – power you through until you reach the end of that day and drop back into your bed. And then, the next day, you resolve to yourself that you just need to get through this day. You take it one day at a time, literally, and each day, you learn a little more about what you’ll need to do to get through. You learn a little more about where to apply your limited spoons, how to manage your emotional energy and who to spend it with.

And as you do so, you get those little reminders that depression is a liar and it lies to you in your own voice. You get the physical evidence that your friends love and care for you, that people value you and that you make the world a better place for all of them. You get those little pebbles that you can throw back at the darkness when you feel it closing in, those tiny little specks of light that don’t feel like very much… but in the dark, even a tiny point of light can make a world of difference.

Refusing to give up means doesn’t mean not letting the depression “win” because it’s not about winning. It’s simply about continuing. It’s about remembering and building and loving, even when it’s hard. Especially when it’s hard. It’s about pushing the gloom back just a little bit and even that little bit can be enough for that day.

Will it be hard? F—k yes it’ll be hard. You don’t need me to tell you that, you’re living it. There’re going to be more folks who aren’t right for you and who aren’t going to respect that you have depression or what depression means. It’s hard to motivate yourself to pursue relationships when it feels like there’s no point and when you feel like your condition will get in the way.

But the fact that it’s hard doesn’t mean that it’s not worth it. Even at those times when “worth it” is a very small feeling at the bottom of a very deep well. It may be hard to see or feel, but knowing it’s there can make a world of difference, even when things are bad. Having those moments, however small, however sporadic, however little of an impact that it feels like they make means that you got through this day, and the next day will be a little easier. You’ll have the resources and reserves to push through another day – even when you’re doing so through gritted teeth and bloody-minded determination.

And keep going long enough and you might keep going long enough to find a new treatment that helps lift that fog.

Things are hard now, but they won’t be forever. Even when it feels that way. You’ll be ok. I promise.

All will be well.

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Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: Two years ago I started taking classes for a hobby of mine, with the main bulk of the attendees being women. Throughout my life I’ve found that I get along with women more than I do men, and it’s very clear that they enjoy my company and feel safe in my presence. As you can perhaps imagine, it’s been easy for me to form friendships within the group, as well as with any of the newcomers that join us.

Naturally, in circumstances where a guy has good relationships with the opposite sex, these friends of mine often wonder why I am single. By all accounts, I’m a cool dude. I don’t really have an answer for it, but there’s a couple of moments which have put me off from even trying.

During my first year at the class, there was a girl (A) who was a regular attendee. We got along well, and always had a good laugh or two. Many of us in the group had exchanged numbers to set up a group chat and arrange meet-ups, but she initiated a text conversation one-on-one for an unremarkable reason. She went on to initiate all of our conversations over text, always with a bit of banter, and this would usually happen after the classes despite having talked during them. From my understanding, these were all positive signs of a good connection and comfort level, as well as potential romantic feelings. After a few months of this going on, I discovered we had a shared interest in another hobby, so I invited her to join me for an event (that I was going to regardless). She declined and stated she was busy, but suggested another rough time-frame that we could do something. When I inquired as to when she might be free, she didn’t reply. In these situations I only ask once, so I bowed out gracefully.

She stopped attending the classes after that conversation. We did briefly reconnect a couple of months later when she messaged me to say she was returning, but she never came back and has been absent for over a year now.

These things happen. Unfortunately, they seem to happen consistently for me.

Fast forward twelve months, and there’s another girl (K) who joins our classes. We spoke on occasion, but nothing substantial. We did eventually exchange numbers, and it was then she began initiating conversations fairly frequently, and with much enthusiasm. On top of this, her interactions with me at the classes developed into a lot of playfulness, which again I took as positive signs. Once again, I learned we had a shared interest in another hobby, and so I extended an invitation for her to join me at an event. She accepted, and for weeks seemed very eager to go, but she cancelled at the last second.

Since then I’ve seen her at the classes, and while she will still talk to me if I approach, it’s clear from her behavior that there is a lot more distance. For instance, she no longer comes up to me to start a conversation, and she doesn’t make eye-contact when we talk. I will, of course, respect this distance.

On both these occasions, I’ve poured over text conversations and revisited interactions in my mind to try and piece together what, if anything, I have done wrong for these women to do a complete 180 in terms of their attitude towards me, and I’ve have had friends look at these conversations and declare I’ve done nothing bad. I went as far as to ask one of the other women at my class if I had ever done or said anything that would make a woman feel uncomfortable, and she confirmed that I was an incredible guy and was amazed I am single.

I understand it may very well not be anything that I have done, but the very idea that I may have made them feel uncomfortable is upsetting to me. It also annoys me that these relationships have been damaged, as I enjoyed their company (especially the second girl). It feels like these women have pushed for something more, but then have pulled back entirely when I do reciprocate. At the same time as being rejected, I’m also losing a friend in the process. This has happened at other times in my life as well, but these are the most recent.

As someone who doesn’t get a lot of romantic interest from women, it’s hard not to take things personally and to put me off the idea of dating entirely.

Three Times Is A Pattern

DEAR THREE TIMES IS A PATTERN: This is another one of those times where, absent documenting every interaction, text and conversation you’ve had with these women, it’s really hard to make any sort of substantive declaration about what you may or may not have done wrong.

However, there’re a couple things in your letter that I think at least hint at things that you should consider examining in yourself and asking if maybe there’s something you should be dealing with.

The first thing is that I think you take things far too personally when there’s absolutely no reason to, and I think you do so in a way that limits your ability to actually learn from these experiences and move forward. In the first example you give, nothing in what you describe suggests that A leaving the class has anything to do with you. Unless you were acting especially egregiously with her, I honestly think that whatever reason she had to drop out wasn’t related to you at all. You mention that you’ve had friends go over those texts; presumably they would’ve said “hey you’re kinda being a creeper as what creeps” if there was anything there.

The fact of the matter is that s—t happens, and s—t occasionally happens in ways that just happen to line up with what you were doing. Absent actual evidence that you had anything to do with A leaving and not rejoining the class, I think you can rest assured that this was just pure happenstance – bad timing that her being busy either escalated or other things were going on that meant that she had to leave the class and hasn’t been able to come back to it.

I would also point out that there’re plenty of times when folks may have every intention of returning to a project, class, interest group or whatnot but just don’t. Sometimes it’s bad luck, with one damned thing happening after another. Other times, they’ve gotten distracted or interrupted and by the time they came back up for air, the window of opportunity closed. Hell, sometimes it’s a hyperfixation thing and when the hyperfixation fades, that project/class/hobby/whatever becomes a source of stress and folks ditch it. This is how a lot of folks with ADHD end up collecting and discarding hobbies and have closets full of half-finished crap to show for it. ��ASK ME HOW I KNOW.

I would also point out that you give up very easily, especially in the face of a not-particularly strong refusal. “Hey, I’m busy that week, but I should be available around $TIME_FRAME” can be a soft no, but it can also be a “I don’t know what my exact schedule is, but let’s aim for this time and see”. I think it would’ve been fine to say “ok, want to tentatively choose a day, or would it be better to check in with you then?” If she didn’t answer one way or the other, I’d give it a day or two and then say “hey, circling back around, I wanted to double check if you’re still free around $TIME_FRAME”.

And honestly, I think it would’ve been fine to say “hey, you haven’t been to class in a couple of days, is everything ok?” That’s not being pushy, that’s just being a concerned classmate and friend. That might’ve at least given you an idea of what’s up, instead of leaving you with nothing but speculation and guesswork that you eventually turned inward.

I do have to wonder if this “bowing out gracefully” tends to look like “pulling back entirely” and leaving the impression that you’re hurt, no longer interested in them or otherwise were only interested in them as a potential date. That would definitely change the tone of the relationship between you and them and make them question just what you were looking for from them. While I doubt that had much to do with A leaving the class, it might explain why things changed with K and why she seems different now.

The other thing I’ve noticed in your letter is that I think you get a little excited when you feel like you’re getting interest from someone, and I suspect that this a) lead you to overestimate the level of interest they have, and b) that excitement means you get a little out over your skis.

I think you may have rounded up interest from both of these women to “potential romantic connection” when it was likely friendship with someone you found particularly appealing. And while I can absolutely understand and can relate to getting excited over the idea that someone may be interested in you… I think you let your excitement get away with you.

Now, I ask this as someone who has made this mistake back when I was younger, less experienced and way more excitable: is it possible that with K, you got a little too caught up in the excitement of going to this event to her and that might have motivated her to change her mind? Looking back on the messages between when you asked her to the event and when she bailed, were you going on and on about future plans or getting very intent on what was going to happen?

I ask because a lot of folks who haven’t had a lot of romantic experience (and I’m including myself from back in the day) can go into… let’s call it excitable puppy mode, where your eagerness and enthusiasm can be a little overwhelming. To you (the general you, not you specifically, TTAP) it’s innocuous. But to the person on the receiving end of it, it can be a lot. To them, it feels a lot like dealing with a cartoon puppy who’s always bouncing around going “hey Spike, what’re we doing today Spike huh huh huh, we gonna go chase some cats, I bet we can chase some cats, we’ll chase those cats good, wanna go chase some cats, Spike, let’s go huh huh huh?” That’s not necessarily malicious or even creepy… but it can give the impression that you’re reading too much into it and it definitely can be annoying and exhausting. Even someone who’s excited to go do the thing with you can decide that maybe she’s changed her mind after being on the receiving end of that sort of behavior. As a result… well, you end up snatching defeat from the jaws of victory and turning a “yes, absolutely” into “Oh look I forgot I have to shave my cat that day.”

AGAIN: ASK ME HOW I KNOW.

And to be clear: none of this is to suggest that you’re the bad guy here or that you did anything egregiously wrong. Without having observed everything or having all the transcripts and witness statements, there’s not much to go on – but nothing in your letter suggests that it was bad behavior on your part.

So it may be worth asking some of your friends if you’ve got a little too much golden retriever puppy energy with folks you’ve just met and if you need to slow your roll a bit. I get that the infrequency of the attention means that you feel like you need to leap on the opportunity, but I suspect that you’re getting more worked up than the situation merits and then being disappointed when it fizzles. I also think you need to not take everything personally, especially when there’s no actual reason to suggest that you were the root cause of someone’s actions. Most people have things going on in their lives that have absolutely nothing to do with you.

At the same time: I think you can afford to be a little less reticent in asking someone out or trying again another time. Sometimes “I’m busy” is a soft no, but sometimes it really is that they’re busy and their schedule’s a mess. You’re allowed to follow up later and see; if they are busy once again, well now you can assume that it was a soft “no” and they can come to you if and when they want to do something. And if they do give a soft no, pivoting back to being friends means just continuing to act like a friend. Part of why folks worry about things being awkward is because people make it awkward. If you continue to be the cool guy and good friend and your behavior shows that nothing’s changed between you and A or K or whomever else? Well, there may be some awkward moments, but you can both power through them and get back to being friends like you were before.

Otherwise, just be a little more chill. I suspect that once you do so, you’ll find that interest from women comes a lot more frequently… and you’ll be in a better position to take advantage when it does.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com