DEAR DR. NERDLOVE: I’m trying to figure out if I like my best friend’s sister and if she likes me back. In other words, I’m trying to see if it’s worth the pursuit. I don’t get to see much of her often but I think about her more than any other girl; I’m introverted and shy so I don’t keep in touch with a lot of my girl friends all that often. Oddly enough, I’ve known her since I was 12 and she just was eight years, I’m 25 and she’s now 21. I’ve kept in touch with her longer than any girl I’ve ever known. I definitely understand that a lot of this might just be that I’ve never been with anyone before and since I’ve known her the longest, I think I can certainly trust her if our relationship develops into passionate one.

One of the things stopping me is that her brother is protective of her. I completely understand this, but frankly, she is old enough to make her own decisions. Also, I think if she was interested she might’ve given me better clues. Although to be honest, I would guess she’d know me well enough to know that I would be very intimidated to start dating the little sister of my best friend.

Since I’ve discovered I had a crush on her, I’ve gone to the trouble of mentioning she looks nice, that I noticed she changed her hair, stating I was shocked she didn’t like how she looked, etc. Sometimes, when we’re all drinking altogether I’ve made sure she gets plenty of water and just makes sure she’s all right. Her stepmom has even commented that I would be a good match for her based how I treat her. However, I think it more like a carefree joke… and I was so embarrassed that I couldn’t say anything.

I’m just not sure how to go about talking to her about this; not just because of her protective brother but because I’m often a bit more sarcastic and I worry she might not take me seriously. If it’s just a simple crush do I even say anything? If I say anything to her about it, do I risk losing my best friend? Maybe I’m reading too much into this but she’s been dating a lot of guys who are ofter shyer than me and even some have looked a bit like me. She does go out of her way to introduce me to her boyfriends and they do seem to be a little protective, almost like they’re jealous. (If I knew better, I’d suspect it to be very Aaron Sorkin-esque relationship.)

Based on how complicated things are, I’ve been trying to meet other people. I’ve made a point to talk about other girls that I’ve gone on dates with and how I wasn’t very compatible with them. On just the couple of occasions that I’ve talked about girls she’s been strangely silent, even to the point where she actually leaves without a word. Her only advice was that she could see me with someone as young as 20. With other friends in our circle she’s a bit more curious how certain things have worked and what didn’t.

I’m trying to figure out if there’s something between us but I worry about what my best friend would say if he found out… I don’t know who to talk to about this stuff.

Stumped Over Sibling

DEAR STUMPED OVER SIBLINGS: Can we cut the bulls

t a little, SOS? Because between you, me and the entire Internet, it’s pretty safe to say you’re interested in your bro’s sister. You don’t need to keep hemming and hawing and throwing conditionals in there to make it sound like you’re not sure if you’re into her or not but you THINK you might be but…

Just be real here. Your buddy’s sister got hot, you have a thing for her. It happens. And that’s fine, man. You’re both adults. The fact that you’ve known each other all this time doesn’t preclude you from recognizing that she got cute, nor does it mean that she’s off limits because you two grew up together. It’s not like you’ve spent all this time waiting for her to come of age. You both grew up, you matured, you changed and now you’re starting to see her as an adult woman instead of an adjunct to your best friend.

So it’s not that you don’t know whether or not you’ve caught feels for her. It’s the potential for unnecessary drama you’re worried about that makes you hesitate to declare that yes, you’re into her.

But before you worry about your buddy, you should decide what you’re going to do about HER. After all, she’s the one you’re interested in, so she’s the one who’s going to be the one to decide whether or not she’s interested in you, too. If you’re interested in her, you should probably find out how she feels before you worry about literally anything else.

And to be perfectly frank, running to her brother for permission is a wee bit patronizing. Doubly so considering that she’s a grown-ass woman. Family is family and they certainly get to have an opinion, but they don’t get veto power – either overtly (“No, you can’t date him, sis”) or by fiat (“Talk to my sister again and I’ll kill you”) over her love life. So if you’re interested in her and want to try to pursue something with her, then maybe you should run things by her first before you worry about her big bad bro.

Of course, you’re not sure how she feels about you. You think you’ve been getting some hints, but the ol’ Magic 8-Ball keeps coming up “Signs Hazy, Ask Again”. So what do you do?

Well, the way I see it, you’ve got two choices. You can spend weeks and months trying to read the tea leaves and divine her intentions from subtle little things that may or may not mean anything. Or – and stick with me, this is a little crazy – you could always ask her out on a date.

Extreme, I know. But it’s a fairly reliable way of finding out if someone wants to date you.

If the two of you are into one another and you’re going to pursue this more than just the odd date or two, then you can worry about her brother. It’s entirely possible that this would be something he couldn’t possibly tolerate and it’d put a strain on your relationship with him. At that point — and not before — would you have to decide which is more important: your friendship with him, or your relationship with his sister.

But if he’s your friend and he knows that you’re a good guy who would be good for his sister, then that shouldn’t be as much of a conflict. It could be difficult if he does have a freak-out – especially since that’s insulting to both you and his sister. 

But as I said: he doesn’t get a veto.

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 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)