DEAR DR. NERDLOVE: I recently reconnected with a sexual partner from my past. We’ve always kept in touch over the past 8 years, but are now trying to have a “normal” intimate, next level relationship.

The problem is …I enjoy quicker “activities” – let’s say 30-40 minutes, including foreplay. He prefers longer sessions and can go for hours without an orgasm. This hurts (he’s well endowed) and even though we try all the positions, 40-50 minutes (at least) of straight penetration is painful. I don’t feel like I’m turning him on enough (although he remains hard and assures me that he’s turned on). Unfortunately, my feelings of “inadequacy” are starting to wear on me. And yes, we’ve tried blow jobs and hand jobs to give my girl a rest, but even a 20 minute blow job (plus foreplay and penetrating), doesn’t help him get there.

The thing I’m worried most about is, I think it’s starting to affect both of us mentally. The other night when we were making out, I asked him to grab a condom and he declined sex…saying he didn’t want to disappoint me. Well, you can imagine how that left me feeling. Part of me thinks he’s okay having sex and letting me get off (even if he doesn’t), but another part of me can’t believe a man doesn’t want to orgasm (I mean, what about, “blue balls?!”).

I’m bummed about it. He says, don’t worry, we’ll get in synch. I don’t know if either one of wants to have sex anymore. Which makes me sad because we have an amazing relationship outside of this. But sex is important to me (and I’m assuming to him, as well). And before you ask, we’ve explored all kinds of foreplay, positions, places, etc…all of that is good.

I think that we’re both starting to experience mental blocks when it comes to orgasms. By the way, before we reconnected, he admitted that he’s always had a hard time reaching climax (but he doesn’t know why). He can reach it if/when he masturbates. And, says, he’s guilty of faking orgasms (with others) in the past. He said, he’s never faked with me — he’s only reached orgasms a couple of times with me; we eventually stop having sex because I’m too sore to continue. Hence, why I try to add other stimulation and find out what he’s doing himself that helps him orgasm when he’s alone.

I don’t know what else to do and I’m afraid it’ll become a problem that we can’t overcome.

Burning Out

DEAR BURNING OUT: Alright BO, there’re a couple things to dig into here. We’ll tackle the easiest one first: blue balls aren’t really a thing — at least, not to the point where folks with dicks and prostates NEED to get off or else we suffer agonizing pain. While not getting off can be frustrating, even a little ache-y around the testicles on occasion, there’re also plenty of times when it’s just not gonna happen, no matter what you do. Sometimes you’re just not going to get whatever x-factor is needed to push you over that particular cliff; at those times, it’s less about pain and more just “ok, I’m never gonna even get close.”

And hey, if he’s ok with not getting off — or taking care of things later — but he’s willing to make sure you have a good time? That’s the mark of a caring and considerate partner.

The bigger issue here is that you and your boyfriend have a sexual compatibility issue. Being sexually compatible is an incredibly important part of relationships; as you and your partner are discovering, when things don’t mesh up well enough, it can damage your relationship overall. The problem is that when we talk about sexual compatibility, we tend to think about things like mismatched libidos. One partner may want sex every day and twice on Sundays, while the other would prefer it once a month, and so on. But sexual compatibility also is about the kind of sex you want to have. If one partner is a dedicated kinkster and the other has a strict preference for standard-issue sex, then there’s a fundamental incompatibility that has the potential to damage or even destroy the relationship.

Similarly, if one partner likes to take things slowly and sensually and the other likes mad, passionate, throw-each-other-around-the-room sex, that can also be an issue.

Duration can also be an issue. Normally the problem is not lasting long enough… but this can also swing in the other direction. A lot of men get it in their heads that longer is better, period. This belief gets hammered into our heads over and over again, from porn to jokes in pop-culture, to hearing about how this celebrity or that can f--k like a champion for HOURS. But  — as you well know — duration and pleasure aren’t the same thing, especially when you’re talking about penetrative sex… and you’re the one being penetrated. While having some hang-time can be useful when a partner needs more stimulation, you hit a point of diminishing returns pretty quickly. Things start to get sore and chafe, lubrication starts to dry up and those sensations can go from “hurts so good” to “ow ow ow STOP IT” damn quickly.

It doesn’t matter what porn tells you; stay at it for long enough and you run the risk of leaving your partner dryer than the Mojave and feeling like a car engine with no oil after a road trip from LA to Vegas.

However, I suspect that the problem you and your partner are having isn’t strictly about compatibility. You mentioned that your partner prefers longer sessions and can go for hours. I want to zero in on this, because I’m wondering whether this is actually a preference, or if that’s an adaptation to circumstances.

See, you mention that he told you that he’s always had problems reaching orgasm through partnered sex, but has no problem when he’s masturbating. That, I think, is an incredibly important clue. I strongly suspect that your partner may have what urologists call “an idiosyncratic masturbatory technique.” You might know it by the name Dan Savage gave it: death grip syndrome.

This is a common issue in folks with penises. They get used to masturbating in a way that uses friction or pressure or other sensations that the human mouth, anus or vagina can’t match. Sometimes it means grasping the shaft incredibly tightly. Other times it may involve using a textured object — anything from a wash cloth to a pillow to inserting themselves between the mattress and the box spring. If someone does this for long enough, they can functionally train themselves to need that particular texture or pressure in order to orgasm. At that point, it becomes difficult, even virtually impossible, to achieve orgasm during partnered sex. This can be frustrating for them and demoralizing for their partner, who often feels like they’re at fault somehow.

Fortunately, the cure for death grip syndrome is fairly simple: they have to retrain their penis. This is achieved by abstaining from their usual masturbation technique — or possibly from masturbation entirely. They can have partnered sex, but they also have to be willing to go without the sensations that lead to their orgasm. By functionally starving themselves of that sensation and denying themselves that orgasm, they’ll often reach a point where their penis will start responding to more typical stimuli and orgasm that way. Of course, this means that they have to forgo their old jerk-off technique for good, otherwise all they end up doing is reinforcing that groove they carved in their brain.

However, it’s worth noting that some folks just have a difficult time reaching orgasm. Just as many people with clits and vaginas require a lot of intense, direct stimulation in order to get off, some folks with penises can need a lot of time or sensation to pop their corks. That’s just how they’re built and wired.

Now that doesn’t mean that they’re stuck wearing out partners who may not be into the marathon f--k sessions they need. One of the options available to the two of you is to vary up how you have sex. And while oral sex and masturbating can get just as exhausting, those aren’t the only options available to you.

I recommend you incorporate toys in the bedroom. To start with, look into getting a masturbation sleeve, like a Fleshlight or a Tenga. There’re a number of options that offer different levels or types of sensation; a number of toys even allow you to adjust the level of pressure or suction from the toy. You can use these as a warm-up to help get him closer, a way of giving yourself a break, or even switch things up between you and the toy and let the different sensations pull him over the cliff.

You might also want to look into anal play and some buttplugs. Butt-plugs, once inserted, put pressure against the prostate, which produces seminal fluid and causes ejaculation during orgasm. Having that in during sex means that the plug will press up on his prostate while he’s having sex with you. The pressure of the plug combined with the nerve-endings surrounding the gland AND the sensation of sex with you could mean that he won’t need to go for hours to get off. And — as a bonus — the pressure against his prostate tends to lead to some truly thunderous orgasms for him.

My recommendation is that you take explore both options, possibly even simultaneously. Having ways to take the pressure off (and friction) off of you during sex and to overcome any death-grip issues can help the two of you overcome this obstacle and get into the groove in bed again.

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: I’ve enjoyed your YouTube channel and just bought your book! I really love your breakdown of topics from both the male and especially the female perspective. Listening to your work has validated for me, I am for the most part… on the right path for a deep, compassionate, loving connection.

Challenge/Problem: I think where my struggle lies or maybe that’s what I feel is that most women (not all) that I choose to date are not accustomed to a man with this much depth or emotions. Often don’t know how to respond, haven’t reflected on themselves or I’ve gotten “you just talk way too much for a guy”. (That lasted a brief 11 days lol) No worries.

I do not see my emotions as a “handicap” or negatively. I am very self-aware, ask a lot of questions, confident, giving and work on compassion and empathy daily. I try to understand a woman’s boundaries, how she likes to receive love and what is the best way to communicate with her. BUT my choices in potential partners to date seem to only want or go one maybe two levels deep in conversation about emotional intelligence and self-awareness. Those two are HUGE for me. I am a natural born conversationalist. I love to initiate interesting conversations via in person or on the phone (audio/FaceTime). Now more so, within FB groups. I’d rather talk than text because texting can only go so far to drive a deeper connection. I don’t offend easily and I like to create a safe space for people to be vulnerable (including myself) and speak freely. With COVID and our current environment my social methods deepened in the online space, both on apps and FB groups.

WHAT I am doing to overcome this challenge: I work in tech and been on dating apps for almost 8+ years. I have literally re-constructed/white boarded iterations of a new app that could pull depth in a person rather than preferences and looks. User experience of Bumble and Hinge seems to be the best for deeper connections. Woman making the first move shows “emotional availability” (they ready) rather than she’s good with seeing her match count go up like a scoreboard. OkCupid I thought was good at first because it lets a man write freely and introspective women love to read and therefore “hear” a man’s voice through his writing. Tried that BUT! I noticed that any guy can message ANY girl and so they are flooded with first time messages.

About me: I am an extrovert, I consider myself a loud “bag of s--t” who has many close platonic female friends “best friends”. I swear, my wedding line and bachelor party would consist of amazing GroomsWomen. I take pride in what I do, Tech Project manager (career) Yoga instructor (Passion to connect and help others)

SO! With that small snippet of what I believe is my challenge to find depth, passion, and emotional intelligence within an impatient, “I want it now”, technological, self-gratifying, unaware, lack of true connection dating pool. You either get lost within the millions OR she lacks the emotional maturity/experience to go deep with me.

……. HELP me

Reflect on this differently. The natural technique of approaching a woman in person to spark up a conversation safely, has gone out the window. Dating apps are saturated with people. It’s either too fast or too slow. Women don’t know how to respond to such depth and if you take the friend route….. now I feel like a mentor.

Cheers,

Talk To Me

DEAR TALK TO ME: I think I can tell you exactly what the problem is TTM: you’re going from 0 to 60 in the span of seconds when you’re talking to people. I’m going to take a wild shot in the dark: are you someone who prides himself in the fact that he hates small talk and wants to get right to the incredibly deep and intimate conversations?

I hear a lot from guys like that, often complaining how hard it is for them to meet women who want to talk in depth about philosophy or plans for the future or making deep emotional connections. The problem isn’t the grandiosity of their vision or the passion they have for philosophy or emotional intelligence or what-have-you… it’s that this is the FIRST THING they want to talk about. And while I get why you might want to leap off with a conversation about love languages or emotional cores… most people don’t want to get that deep with someone they’ve only just met. The issue isn’t that women aren’t used to a guy with depth or emotion, it’s that more often than not, those guys aren’t displaying actual emotional intelligence.

Here’s the thing: having depth of emotion doesn’t mean much if you don’t also have the wisdom to know when to reveal it or deploy it. If you’re trying to get into deep conversations about self-awareness immediately… well, most folks aren’t going to want to follow you there. You rarely have built up the connection with them that would make them feel comfortable with you. You may be proud of the depth and breadth of your emotions… but you’re not paying that much attention to theirs. 

One of the reasons why things like small-talk are important is that it’s the comfort and connection building phase of meeting someone. Think of the conversation you want to have like a freeway. Small talk is the on-ramp to that particular freeway. By getting to know someone, making those early, initial connections, you’re taking the on-ramp, merging seamlessly at the flow of traffic. The way you seem to be approaching things is the conversational equivalent of trying to just plow straight onto the freeway with no warning whatsoever. That’s a great way to either end up in a car crash or cause one for someone else. Which, in this case, is why you’re getting people who tell you that you talk too much “for a guy”.

If that’s all you want to talk about, especially with someone you’ve only just met? I’m not the least bit surprised that you’re getting resistance. That’s simply not how most folks operate. And your unwillingness to concede that maybe your approach isn’t working out for you is going to be the main reason that you aren’t finding these connections, rather than an impatient, pool of unaware people who lack true connections because of dating apps.

So, you basically have a choice. You can either keep going as you do and hope to find the rare bird who works on the same wavelength that you do. Or, you can adjust your approach and slow your roll. You can dial things back, spend some time getting to know somebody, getting comfortable with them and being more aware of their feelings, interest and comfort, instead of charging in like you’re auditioning for the conversational equivalent of the next Fast and Furious movie.

A little more time working on empathy and connection and a lot less time judging people and making assumptions about them because they don’t move on your exact schedule or your exact preferences will go a long way towards your meeting some women who actually do want to talk about emotions and get into deeper, more meaningful topics. But not if you either drive them away by not paying attention, or assume they’re shallower than you just because they aren’t your conversational clone.

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: I’ve enjoyed your YouTube channel and just bought your book! I really love your breakdown of topics from both the male and especially the female perspective. Listening to your work has validated for me, I am for the most part… on the right path for a deep, compassionate, loving connection.

Challenge/Problem: I think where my struggle lies or maybe that’s what I feel is that most women (not all) that I choose to date are not accustomed to a man with this much depth or emotions. Often don’t know how to respond, haven’t reflected on themselves or I’ve gotten “you just talk way too much for a guy”. (That lasted a brief 11 days lol) No worries.

I do not see my emotions as a “handicap” or negatively. I am very self-aware, ask a lot of questions, confident, giving and work on compassion and empathy daily. I try to understand a woman’s boundaries, how she likes to receive love and what is the best way to communicate with her. BUT my choices in potential partners to date seem to only want or go one maybe two levels deep in conversation about emotional intelligence and self-awareness. Those two are HUGE for me. I am a natural born conversationalist. I love to initiate interesting conversations via in person or on the phone (audio/FaceTime). Now more so, within FB groups. I’d rather talk than text because texting can only go so far to drive a deeper connection. I don’t offend easily and I like to create a safe space for people to be vulnerable (including myself) and speak freely. With COVID and our current environment my social methods deepened in the online space, both on apps and FB groups.

WHAT I am doing to overcome this challenge: I work in tech and been on dating apps for almost 8+ years. I have literally re-constructed/white boarded iterations of a new app that could pull depth in a person rather than preferences and looks. User experience of Bumble and Hinge seems to be the best for deeper connections. Woman making the first move shows “emotional availability” (they ready) rather than she’s good with seeing her match count go up like a scoreboard. OkCupid I thought was good at first because it lets a man write freely and introspective women love to read and therefore “hear” a man’s voice through his writing. Tried that BUT! I noticed that any guy can message ANY girl and so they are flooded with first time messages.

About me: I am an extrovert, I consider myself a loud “bag of s--t” who has many close platonic female friends “best friends”. I swear, my wedding line and bachelor party would consist of amazing GroomsWomen. I take pride in what I do, Tech Project manager (career) Yoga instructor (Passion to connect and help others)

SO! With that small snippet of what I believe is my challenge to find depth, passion, and emotional intelligence within an impatient, “I want it now”, technological, self-gratifying, unaware, lack of true connection dating pool. You either get lost within the millions OR she lacks the emotional maturity/experience to go deep with me.

……. HELP me

Reflect on this differently. The natural technique of approaching a woman in person to spark up a conversation safely, has gone out the window. Dating apps are saturated with people. It’s either too fast or too slow. Women don’t know how to respond to such depth and if you take the friend route….. now I feel like a mentor.

Cheers,

Talk To Me

DEAR TALK TO ME: I think I can tell you exactly what the problem is TTM: you’re going from 0 to 60 in the span of seconds when you’re talking to people. I’m going to take a wild shot in the dark: are you someone who prides himself in the fact that he hates small talk and wants to get right to the incredibly deep and intimate conversations?

I hear a lot from guys like that, often complaining how hard it is for them to meet women who want to talk in depth about philosophy or plans for the future or making deep emotional connections. The problem isn’t the grandiosity of their vision or the passion they have for philosophy or emotional intelligence or what-have-you… it’s that this is the FIRST THING they want to talk about. And while I get why you might want to leap off with a conversation about love languages or emotional cores… most people don’t want to get that deep with someone they’ve only just met. The issue isn’t that women aren’t used to a guy with depth or emotion, it’s that more often than not, those guys aren’t displaying actual emotional intelligence.

Here’s the thing: having depth of emotion doesn’t mean much if you don’t also have the wisdom to know when to reveal it or deploy it. If you’re trying to get into deep conversations about self-awareness immediately… well, most folks aren’t going to want to follow you there. You rarely have built up the connection with them that would make them feel comfortable with you. You may be proud of the depth and breadth of your emotions… but you’re not paying that much attention to theirs. 

One of the reasons why things like small-talk are important is that it’s the comfort and connection building phase of meeting someone. Think of the conversation you want to have like a freeway. Small talk is the on-ramp to that particular freeway. By getting to know someone, making those early, initial connections, you’re taking the on-ramp, merging seamlessly at the flow of traffic. The way you seem to be approaching things is the conversational equivalent of trying to just plow straight onto the freeway with no warning whatsoever. That’s a great way to either end up in a car crash or cause one for someone else. Which, in this case, is why you’re getting people who tell you that you talk too much “for a guy”.

If that’s all you want to talk about, especially with someone you’ve only just met? I’m not the least bit surprised that you’re getting resistance. That’s simply not how most folks operate. And your unwillingness to concede that maybe your approach isn’t working out for you is going to be the main reason that you aren’t finding these connections, rather than an impatient, pool of unaware people who lack true connections because of dating apps.

So, you basically have a choice. You can either keep going as you do and hope to find the rare bird who works on the same wavelength that you do. Or, you can adjust your approach and slow your roll. You can dial things back, spend some time getting to know somebody, getting comfortable with them and being more aware of their feelings, interest and comfort, instead of charging in like you’re auditioning for the conversational equivalent of the next Fast and Furious movie.

A little more time working on empathy and connection and a lot less time judging people and making assumptions about them because they don’t move on your exact schedule or your exact preferences will go a long way towards your meeting some women who actually do want to talk about emotions and get into deeper, more meaningful topics. But not if you either drive them away by not paying attention, or assume they’re shallower than you just because they aren’t your conversational clone.

Good luck.

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