DEAR DR. NERDLOVE: I’ve read some of your articles and wanted to first off say thanks! So here’s some details about myself:

I’m a 30 yr old male with a successful career. I’ve never had a hard time attracting attractive women but I’m very sexually inexperienced due to failed sexual encounters, lack of confidence and anxiety, which I believe has led to 0 serious relationships.

I got into porn at a very young age (13 maybe) and masturbate to it regularly with the initial emphasis being to get it over as soon as possible. I always lie on my back in bed while doing so and have never deviated. I also started with a squeezing motion at a young age as opposed to an up and down motion so I’m guessing I’m the victim of the dreaded “death-grip”. Only in the past few years have I adopted the stroking motion but still apply heavy pressure, especially near climaxing.

Upon my first sexual encounter (age 25) and numerous encounters thereafter, upon penetration, I go from erect to completely soft almost instantly. During foreplay I’m very aroused, and seldom never “lose it”. In addition, I’ve experienced situations where I get only like 70% of an erection, where I can’t even penetrate. Upon failure, I go to 0% and that’s pretty much game over.

I get great morning wood (100% erection) and can get these when masturbating alone, typically after smoking marijuana. Otherwise, I get about 70% when sober.

No woman has ever been able to get me to orgasm via oral, either

Now that I’ve set the table a bit, what can I do to get better in the bedroom and get/keep 100% erections? I find myself fearful of evening trying anymore due to the embarrassment that follows after failed performances. I just want to be able to make love like a normal person! I’ve already started working out and trying to eat healthier but any tips or advice at all to try would be immensely appreciated!

Thanks in advance!

Junk For Junk

DEAR JUNK FOR JUNK: You have two issue here, JJ.

The first issue is simple. You’re absolutely right: you’ve basically carved a groove into your erotic brain and that’s interfering with your sexual response patterns and making it impossible to get off when you’re having partnered sex.

You’ve set yourself up with a very specific pattern for when you masturbate, and since you never deviate from it, it’s become more or less what you need to get off. That’s going to be a problem, because people are almost never going to f

k the way you jerk off. You’ve trained yourself to need very specific form of stimulation — that squeezing motion you mention — that simply isn’t something that the human vagina, anus or mouth can recreate. Just as importantly, you’ve taught yourself that you need a level of pressure that, again, internal muscles will never be able to match. As a result, penetrative sex is never going to get you to where you need to go, leaving you frustrated and less than 100% solid.

Now the fact that you trained yourself into this pattern means that you can train yourself OUT of it. It’s just a lengthy and difficult process. The key is that you need to starve yourself of sexual stimulation, to the point that your junk, your nerve endings and your brain are all desperate for ANY sort of contact in order to get off.

So you’re about to go on a fap-free diet from now until… let’s say, Halloween to start. That means that you now have a strictly hands-off policy with your penis. It is now purely for urination and decoration. You don’t touch it except to use the urinal or avoid getting caught in your zipper. You do not masturbate. At all.

The point of the exercise is to to let that frustration build and build until you can’t take it any more. And then you let it continue to build because you’re not there yet.

This is going to be difficult. REALLY difficult.

(Notice how carefully I refrained from saying “this will be hard”. Appreciate my restraint.)

You’re going to want to get off in the worst way. You are going to feel like you’re at the bursting point and surely by now you can take matters into your own hands.

Well, no. Not yet. It’s still too early. And don’t call me Shirley.

When you reach the point where you think your prostate is about to explode because you are just THAT backed up… then and ONLY then are you allowed relief. However, you’re NOT going to use your usual masturbation habits. You are forbidden from jerking it — or squeezing it, really — the way you always have. You’re going to switch things up. You’re going to use your other hand. You’re going to use a feather-light touch. You’re going to get yourself a Fleshlight or a Tenga Flip and some lube. You are going to take things very slowly, instead of the “get it done as fast as I can” method you’re used to. You’re going to do ANYTHING other than using your squeeze-play… which, I note, you’ve been falling back to even when you’ve been trying to switch things up.

The point of this exercise is that once you’ve starved your penis to the point that it’ll accept any stimulation is to carve a different groove in your brain — one that’ll let you be able to get off through standard penetrative sex with another person. That’s why you need to start getting yourself in the habit of using techniques that don’t use a literally impossible level of pressure or friction. If you use your old technique, all you’re going to do is reactivate those old neurons and fall right back to where you were before, with a penis that won’t respond to anything but your very idiosyncratic masturbation technique. So from now on, your squeeze-technique? It’s off-limits, because no human body can replicate that level of pressure.

But here’s the other issue you’re having: your inability to get off with another person has destroyed your confidence and without confidence, your boner simply isn’t gonna work.

Erections are like faeries in Peter Pan: they only work as long as somebody believes in them. They’re little divas who want everything to be perfect and if anything is even a smidge off, they’ll throw a tantrum. That’s they melt like the Wicked Witch of the West as soon as you don’t believe it exists.

(Yes, I just crossed the fictional streams; I’m on a roll here.)

You were already anxious about being with someone else and so you were less than rock steady and ready to go; instead it was more like trying to shoot pool with a rope. Once that anxiety became part of your experience, your worries about being unable to come or to please a woman have become a self-fulfilling prophecy – you’re expecting to lose your erection, and so you do.

The solution here corresponds with the solution to your breaking your death-grip cycle: take penetration off the table. Your fingers never go soft. Neither does your tongue. Neither do sex toys. So bring all of those into play. Use your fingers on your partners like you’re back in high-school. Go down on for so long that you’ll have to learn how to breathe through your ears. Use a vibrator on them.

This will not only have the benefit of taking the fear of a soft or non-existent erection out of play, but it’ll make you a MUCH better and more desirable lover. Most women can’t achieve orgasm through penetration alone, and men rarely give enough time to foreplay. The more practice you have at pleasing women that aren’t centered around your penis, the better you’ll be overall.

And when it’s time for them to reciprocate… they can give you hand-jobs or oral, but no penetration until you’re starting to get past the whole “I can only orgasm in this one, incredibly idiosyncratic way.”

The more you start to realize that there’s more to sexual pleasure than just your penis, the more you’ll realize that not rising to the occasion isn’t the dilemma you think it is. It just means you switch gears and use the other tools you have at your exposure until you ARE ready.

It’s a matter of practice, endurance and some willingness to clap your metaphorical hands if you believe… but you’ll get there.

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’m in my late twenties, married, and very happy with my relationship. Both my spouse and I have a best friend we’ll call Keith. Keith has been our BFF for over 10 years, and I love him so very much. He’s befriended my spouse and I right after we started dating – so I’ve never been single around him, and he’s witnessed the whole gamut of my spouse’s and my relationship: falling in love, having arguments, making up, getting engaged, getting married, buying a house, etc. He’s a big part of our life: he hangs out with us almost every day, we go on vacations and trips together occasionally, we’ve leaned on each other for emotional support though job losses and family deaths, etc. Point is, he’s a REALLY important friend to both my spouse and me.

The “problem” is… I’m pretty sure Keith is in love with me. Like, for real in love. He’s basically admitted it, in a long round-about way. He doesn’t date, he hasn’t had a significant relationship (more than 2 weeks or so) in the 10+ years I’ve known him. He’s open about how attractive he finds me, and that I’m the “kind of” woman he wants. And while he is just as kind and close to my spouse, he has told me privately many times that he thinks I’m just the bees knees.

Now, let me be clear that my spouse and I have no problem with poly relationships and we’ve even discussed the fact that both of us would be OPEN to it if the right person came along (we’re both bisexual, if it matters). But neither of us are attracted, sexually, to Keith at all.

I don’t know if there’s a “problem” here – Keith isn’t pressuring me to leave my spouse nor has he explicitly asked to be romantic with him (with or without my spouse’s approval). But I’m beginning to worry he’s hung up on me and won’t move on to someone else. Every time he tries to date, it never seems to work out. A lot of times it seems like the other girl’s fault, but I’m only hearing one side of the story. From my perspective it doesn’t seem like he spends much time on grooming or pursuing them because he’s far more interested in hanging out with us. He compares all other women in his life to me, I’m afraid.

(And I just have to point out, I have no idea why. I’m trying to not come across as conceited)

I know he’s not asexual. I know he wants a girlfriend or boyfriend. I know he’s lonely (he talks about!) I KNOW he would want a partner if the right one came along. But I know firsthand how hard it is to move on when you’re REALLY hung up on someone else.

I don’t want to feel like I’m keeping him “on the hook” – I’ve never tried to give him any signals that we’ll ever be more than friends. But I’m just worried sick he’ll never be happy with someone else if he’s pining over me.

Part of me thinks I should try to distance myself from him, you know, “be cruel to be kind” and all that, but I love him (platonically) so much!!! He’s my best friend, and I know I’m his. Should I just… let him deal with it and stay out of it?

Help?

Putting the ‘Friend’ in Friend Zone

DEAR PUTTING THE ‘FRIEND’ IN FRIEND ZONE: I picked your letter PTFFZ because, for all the times we hear about dudes complaining about being Friend Zone’d (which, as I like to point out, doesn’t exist), we don’t often hear from the perspective of someone who’s been “girlfriend-zoned”.

So you’re providing a much-needed look into what it’s like to be on the other side of somebody’s inconvenient crush – you genuinely like the guy, but you don’t LIKE-like him. You’re legitimately worried that you’re somehow encouraging him to keep on hoping, knowing full well that it’s just never going to happen.

For all of my readers who’ve been friend-zoned… this is what your crush’s been going through. This isn’t a malicious “ha ha, dance on my string, puppet” issue or some bulls

t “ladder theory”, it’s a friend worried about another friend’s well-being.

With that out of the way, PTFFZ, let’s get to your situation.

It says a lot about you and your connection with Keith that you’re this concerned about him and the possibility that he’s holding out hope that maybe you’re going to come around on him. It’s very sweet of you to be concerned… but ultimately it’s ALSO not your responsibility.

The thing is, Keith’s a grown-ass man. He’s making his own choices. If he does have a nasty case of Oneitis for you, there’s really not anything you can do. I can tell you from bitter personal experience: Oneitis is not rational. It’s not logical. It’s not that they can’t let go, it’s that they WON’T. Somebody with Oneitis will take anything as reason to believe that if they just hold out long enough, the universe will reward their heroic devotion. They will pass up on other relationships because it would be a “betrayal” of their love.

It could be that he’s hung up on you. It could also be that he’s hung up on you and your husband. Some people get crushes of a sort on couples and see their relationship as a sort of surrogate for the one they want. And with all the time he spends with the two of you… well, it’s like he’s an unofficial third, no?

Are you keeping him on the hook? To be honest… probably not. It certainly can be worth interrogating your behavior with Keith, and examine whether you’re, say, being physical with him in ways that you might not otherwise be with other male friends. But really, unless you’re actually flirting with him or saying things like “you know, in another life, we’d probably be a scorching couple”, then odds are that he’s keeping himself on the hook.

9 times out of 10, the issue is that the guy in question is taking perfectly ordinary behavior – even friendly physical affection – and treating it as a sign of potential interest. And while it’s true that a lot of guys can be touch-starved or aren’t used to physically affectionate friendships, it’s ultimately on them to manage their expectations or emotions. He’s not your child. He’s an adult with agency and responsibilities and it’s not on you to do his emotional labor for him.

It’s good that you care for him and that you worry, but you can’t force him to not want you and you can’t force him to be interested in other people. That’s all on him. You can gently nudge him in the right direction. Hell, you can get him copies of some of my books in hopes that it’d help him develop the skills he needs. But you can’t make him do anything.

Honestly, the only thing you could do is dial back the level of emotional and physical intimacy you have with him in hopes that things will taper off. If he’s using you – or your husband, or both of you – to be his surrogate relationship, then this will pull back his emotional safety blanket.

In practice however, I suspect that this will be more likely to trigger a confrontation and conversation about his feelings for you.

Maybe that needs to happen… if you’re right and he’s hung up on you. But at the end of the day: any progress he makes is going to have to be his choice. You can’t live his life for him.

Wish I could give you a more clear-cut “this is what you need to do,” but like I said: dude’s a grown-ass man. The only person who can make him move on is him.

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: My best friend works at a games store. I visit her about twice a week in between days I have class to bring her food and keep her company when there’s low foot traffic. A couple weeks ago, I met one of her coworkers, who she’s talked about quite a bit. I’ll be honest, I was judgy and expected to not like this guy based on her description. She made him out to be a very extroverted person and that isn’t the sort of person I mesh well with. But this guy. He’s incredibly attractive and very funny. And he’s genuinely nice! My interactions with him have been limited, but there’s definitely the beginnings of a crush brewing. I mentioned to my friend that I thought he was cute and she immediately prattled off a list of reasons why he’s so great. Damn.

In the past month or so, I’ve unpacked a lot of my own emotional issues related to some past heartbreak. I feel now that I’m better equipped to try and seek out a relationship. But I’m not sure whether it’d be smart to take the risk on this guy. My friend told me that, although she’s only known him to date girls, everyone else at the store suspects that he isn’t straight. I myself am a bi guy, so that should be good news. But the uncertainty is terrifying. The thought of just straight-up asking this guy if he likes guys petrifies me. Another friend suggested I just ask him out and see if he says yes. That’s out too.

If I were to do either of those things, I’d want to get to know him better first, but I’m hesitant. I haven’t gone through the trials and tribulations of getting to know someone and then asking them out in a very long time, and I’m frankly scared to do so. I’ve had my heart broken too many times to count, and I’m just now coming back from it. Am I just setting myself up for that again by thinking of pursuing my interest in this guy? Is it worth the risk?

Sincerely,

Cryin’ Bi

DEAR CRYIN’ BI: There’s no reward without risk CB. No matter who you are, no matter what your circumstances, there’s never going to be a point where you can date someone without the risk of pain or disappointment. Whether it’s the pain of being rejected, the pain of being into somebody who isn’t as into you, the pain of breaking up or what-have-you, there’s always the chance of getting hurt. There’s no getting around that.

The key, then, is to decide whether or not that risk is worth it.

Now that doesn’t mean that pain is inevitable, nor does it mean that all pain is equal. Just as we can manage our odds when we play blackjack, we can manage the potential pain of rejection. Part of that is very simple: don’t f

k around and invest so much in somebody you don’t know that you give them the power to destroy you if they turn you down. One of the ways folks end up screwing themselves is that they spend time trying to maximize their chances of getting a “yes” when they ask someone out without actually getting around doing the asking. Before long, they’re so emotionally invested in that person that they don’t dare ask for fear that they’d be turned down and have all their dreams be destroyed.

On the other hand, asking them early means that if you do get turned down… well, it kinda stings, but it ain’t that bad. You’ll likely get over it within the span of time it takes to get a beer, if not sooner.

So, like ripping off a bandage, it’s best done early, quickly and in one smooth motion. As a general rule, I’m a big believer in the Just Ask Him Out, Already approach. By asking someone out on an unambiguous date – not to “hang out some time”, not to “get together” but an actual date – you find out whether they’re into you or not and get a date at the same time if they are. Waiting around “until the time is right” or “until you know for sure” or “know him better” tends to just up the stakes until they’re so high that you don’t dare risk it.

Now that having been said: the fact that you’re bi and you don’t know if this guy is into men means that there’s some legitimate risk here. Plenty of LGBTQ folks, as well as straight women, have been on the receiving end of full-scale freak-outs from sh

ty people, ranging from yelling to outright assault. That’s a legitimate reason to be cautious. But I’m assuming that your BFF knows this guy well enough to know whether he’s the kind of person who’d lose his s

t at a man flirting with him or if he’s the sort of person who would take it in stride. So if you want to be a little cautious here, I’d totally understand. You could conceivably try to thread the needle by inviting him into a convo between you and your friend while you talk about dates and boyfriends previous and see what he says. You could try to feel him out through questions, though that has a higher potential for comedic misunderstanding than actual, actionable intel.

Or you could just cowboy up and say “hey, I don’t know if you’re into guys, but if you are, I think you’re kinda awesome and I’d love to take you on a date sometime.”

But even if you don’t necessarily go for this guy, at some point you’re going to have to get back in the pool. And you can either torture yourself by trying to ease in one millimeter at a time… or you can just dive straight in and start splashing around immediately.

Up to you. You know my vote.

Good luck.

DEAR DR. NERDLOVE: I have a question for you. I’m a kinda short, black teenager in high school and this year (junior year) I decided I want to dress in matching clothing and have some style as much as possible.

So basically I’m not a “socially-inept nerd” but I am a sports playing nerd. I can match my clothes but being in style is hard. I would like your tips on style and maybe some of your style. Thanks.

Jumbled-Up Junior

DEAR JUMBLED-UP JUNIOR: My first rule about high-school is: try not to worry too much about high-school. It’s a giant morass of surging hormones, social Darwinism and a whole bunch of proto-sociopaths who’re busily sharpening their metaphorical knives on anyone and everyone around them where the rules of engagement seem to have been written by people who spent twenty to thirty years in the high-security wing of Oz (and I don’t mean they were trying to find ruby slippers for the Wizard).

Now that having been said, high-school is a place for laying the groundwork for who you will become later on. The sooner you master the basics, whether it’s with social interaction or sartorial mastery, the easier you will find that aspect of your life later on when it does start to count: in college.

So with that in mind, I’m going to advise you that you don’t worry too much about your personal style yet. Start off by making sure you have the basics down pat. This means making sure you’re wearing clothes that actually fit rather than trying to hide any flaws you may perceive in layers of clothing.

Next, keep some simple rules in mind:

First: don’t go overboard with flashy clothes; stick to one piece of clothing that’s the centerpiece of your outfit. Everything else should be basic, otherwise you start to make yourself look overly busy. Same with accessories: keep it simple and minimalist. The more attention-grabbing a piece is, whether it’s a hat, jewelry, a flashy watch or what-have-you, the more it’s going to overwhelm everything else. Think of it like a point system; the flashier it is, the more points it’s going to cost, therefore you will have less room for other accessories.

Next: jeans should be the work-horses of your closet; they can work with any outfit, provided they’re good quality and fairly minimalist in design. The more holes or unusual washes (sand-blasted, for example), the less you can do with them. Dark washes are ideal, as they will work with damn near everything you own and can be dressed up or down. And no decorations on the back pockets. The early 00s have many fashion sins to answer for.

Next: The last thing you put on is going to be the first thing people notice. Keep this in mind, especially in the autumn and winter months. Never underestimate the power of a cool jacket.

Regarding geek-oriented clothing: I’m a big fan of keeping displays of nerdery simple and understated. For example: I wear a custom-made Green Lantern ring, but most folks would never notice until they looked carefully at it. Graphic tees reproducing comic covers, movie posters or X-Men fight-scenes tend to be too much; something simple like the S-shield or the symbiote white-on-black Spider-Man logo are iconic and classic, especially when that’s your centerpiece.

When it comes to shoes: I realize some styles, especially hip-hop and streetwear styles prioritize tennis shoes or basketball shoes. Personally, I think athletic shoes are best used for being athletic in order to keep them from wearing out too quickly. Keep some casual shoes for every-day wear, whether they’re Chuck Taylors, Vans, Addidas or what-have you. You also need one pair of shoes that goes with a suit.

Related to that: your belt should match your shoes.

Also: white socks are best for working out. Dark socks work best for every other occasion.

Track suits are for warming up before exercising or lounging around the house when you don’t give a damn who sees you. Period.

You may notice I didn’t say much about style here. This is because style is an extension of who you are and at your age, your identity and archetype is going to be a moving target. This is a good thing; you should be experimenting with different aspects of your personality and identities as you try to find out who you really are. Find styles that speak to you and people who can serve as a fashion role-model. Just don’t try to lock yourself into who you think you should be or let other people tell you who you are.

This is also a good time to start learning how to shop for clothes properly. Start learning to take advantage of sales and where to find discounts. There are also sites that have daily sales and overstock sales that can help you find designer clothes at a fairly sizable discount.

More often than not, when it comes to clothes, you get what you pay for – but that doesn’t mean that you can’t get it for cheaper if you’re smart.

Good luck.

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