DEAR DR. NERDLOVE: Hi, it’s me again. I left a question earlier this year about my polyamorous boyfriend calling me controlling and now I’m back. I eventually broke up with him, reluctantly, and we were mad at each other for a while. But he told me he was sorry, and I said I was willing to try polyamory again.

That was clearly stupid. He shunned me a bit, and I broke up with him, to his later comments of “I was planning to break up with you soon anyway. She and I never have arguments like I do with you.” (that hypocritical butt. Like 2 weeks later he had three arguments with her in a row.) And also, before the first time he announced he was poly, he had spent a week trying to convince me that he didn’t like her.

Anyway, (you can clearly see I have ADHD) we became friends again and he helped me with my problems.

Then, at the beginning of this year, I realized I liked my best friend who lives pretty close. Just to get it off my chest, I told my ex-bf that I still liked him. I don’t know if I really do still like him, I just liked our relationship. I had a pretty terrible, abusive relationship before him, and he was like the only person I didn’t lose feelings for halfway through. So anyway, he tells me he doesn’t like me back, and I get set up with my best friend by a mutual friend of ours, and we start dating. Dating her feels more comfortable than being friends because for some reason it was always kind of awkward. It’s like it was meant to be.

About a week into our relationship, my ex texts me and says he still loves me, and is losing feelings for his girlfriend (who was the one he was dating while dating me) As you can imagine, I was like, REALLY MAN? I accidentally let it slip to his girlfriend later that he was losing feelings for her, and she was mad at him. I told her that it was better to break up than be in a failing relationship, and they broke up. Now, back to my relationship.

As much as I love her, I’m now for some reason starting to lose feelings for (my best friend). I want our relationship to be like the one with my ex before it went bad. But I know if I break up with her, the rest of our whole EXISTENCE together will be awkward and we might not even be friends. It’s so hard to avoid each other since we have a lot of the same classes. I don’t want our friendship to fail, but she’s also a great girlfriend (though she sometimes can be embarrassing). I’m kind of lonely in life, and my close friend group is crumbling. Most of us just date each other, scared to branch out. So yeah. In conclusion, my life is, well, a tornado would be an understatement.

I know this is a lot of questions and a lot to unpack, but HELP.

Life Is Like A Hurricane

DEAR LIFE IS LIKE A HURRICANE: I’ll be real, LILAH: it sounds like things are kind of a hot-mess express right now and maybe you should be dealing with that instead. Sometimes the problems we become most concerned with aren’t the ones we need to prioritize; they’re just the ones that just feel more important either because they’re the most recent or simply because they feel like one we can actually get our hands around.

The thing is: those problems tend to be symptoms rather than root causes, reflections of the real issue that just seem more manageable because they’re not so systematic. They’re often much simpler than they feel, but we put greater importance on them because we feel like maybe we actually can resolve those, even though there’re bigger and much more impactful issues lurking behind them.

I bring this up because you drop a couple pretty big clues about the real issues in the end of your letter: you feel lonely and you feel like your social circle is falling apart. And to be blunt, I think the group has already fallen apart; it’s just that nobody wants to admit it. 

And to be even blunter,  it sounds to me like some of this is a self-inflicted problem. Your situation with your ex-boyfriend is a prime example. I stand by what I said in your previous letter: I have no idea why in pluperfect f--kery you were dating him and why you’ve tried to stay friends afterwards considering the way you’ve both behaved. He’s either not able to be honest with himself or with you about how he feels and he seems to be stuck in a loop of wanting whichever person he ditched the last time. You on the other hand aren’t covering yourself in glory, either. I’m sorry but I’m going to have to call bulls--t on your ‘accidental’ disclosure that he was supposedly losing feelings for his girlfriend. You decided to chuck a bomb into his relationship, apparently out of spite for the way he’s been behaving and frankly that’s not cool. Even in a poly relationship, it’s not your place to get involved, especially since you had already decided you weren’t interested in seeing him again. Especially when you’re already feeling hurt by his seeming inability to decide who he actually wants to date and why.  

And look, I get it. I’ve got ADHD as well, I know how rejection-sensitive dysphoria can f--k with you and how ADHD plays merry havoc with impulse control. I can also see where the desire to be a chaos goblin with a vengeful streak can be very appealing. But this is precisely the sort of s--t that’s going to cause friend groups to fall apart. If the rest of your social circle is composed of similar drama llamas, I’m not exactly surprised that you’re locked in a cycle of dating Gotterdammerung. 

But the issue with your current girlfriend – and to an extent, your ex-boyfriend – is pretty simple and rather obvious in its simplicity. In and of itself, the problem is that you may be attracted to your friend, but you rounded that attraction up to “love” when there simply wasn’t enough there to sustain it. Under other circumstances, you might’ve had a one-off hook-up or a quick fling and learned that you weren’t compatible in the long-term. But because you were on a mission, you invested far too much and made things complicated.

And this was something you could’ve avoided if you addressed the actual underlying problem. You hit on the issue yourself at multiple points in your letter: you don’t want your ex-boyfriend back so much as you want The Relationship (in capital letters), and you thought your best friend would be able to replace him like an understudy filling the role when the original performer is unavailable. This is an almost literal example of trying to shove someone, anyone into a hole marked “Relationship”, regardless of whether they actually fit. When your ex-boyfriend couldn’t stop being an indecisive flake, you tried with the next easiest candidate and, surprise surprise, it’s not working there, either. But because you made this A Production, now your friendship with her is at risk too.

You’re lonely. I get it, I really do. I empathize with that. You want to stop feeling lonely and, like everyone else, you want to love and be loved. The problem is that you’re focused on The Relationship and not on people you might want to have a relationship with and unfortunately, that’s not going to work. The Relationship you’re thinking about – the one you theoretically had with your ex and want to find again – really only exists in your head. It’s not going to manifest in the real world, no matter how much you will it to, because you’re trying to cast people to play parts, not actually dating them. If you were to let things develop organically instead, you might find someone you could actually connect with. But then it wouldn’t be the exact Relationship you’re imagining; it would be a different beast entirely.

Here’s the thing: you’re lonely and you’re worried that your group of friends is about to crumble and leave you even more alone than you feel now. That’s the bigger issue at hand. I think you would do much better to stop worrying about dating and focus more on why your circle is falling apart and what can be done about it. And the answer may well be “nothing”; you may be in a period where this group simply cannot stay together the way that things currently stand and part of what you’ll need is to learn the lessons about why it crumbled so that you can avoid those mistakes the next time around. Owning your own part in it will be important. So too will recognizing how others contributed. If you can take those lessons, apply them and let them be an opportunity to grow, you may find yourself in a better position to build and grow a new network – one that’s stronger, more resilient and less prone to drama.

In the meantime, I think you may need to let your romantic relationship with your bestie simmer down while you process these lessons and deal with these feelings. If you want to be with her, you should be with her because you want to be with her specifically, not because you simply don’t want to be alone. That’s not fair to either of you, and that’s the sort of thing that will damage a friendship beyond the point of repair.

I’m sure you’ve heard the phrase “you have to put your own oxygen mask on first before helping others with theirs”. Well, this is one of those times. You need to sort out your s--t – processing your understandable complicated feelings about your ex and your behavior with him, your feelings for your BFF, your anxieties about your social circle – before you worry about actually dating. Otherwise, you’re going to run into the same problems over and over again. The only difference will be the faces they’re wearing at the time.

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: This isn’t really a dating question (we’re married) but I hope you’ll still consider answering it.

My husband is excellent. He’s kind, funny, I love to cuddle him. We have great fun together and are super compatible, but we are having problems in the bedroom.

We just can’t seem to make penetrative sex work for us. I suspect that he may have some death grip issues (he can only come from hand jobs, and likes a very firm grip, very fast at the end). He is considerate and always gets me off too (again manual or oral sex) but penetrative sex just doesn’t work. This is a problem because I really miss it.

We have been together for about 4 years total and he has come through vaginal sex only a handful of times. It has to be with me on top (not my fave) and working pretty hard, holding a particular angle that works best for him, usually for a long time. Lately it’s gotten to the point where I am starting to feel disappointed and I think this could harm our connection.

I don’t want him to sense disappointment from me, because I’m worried that could completely kill our sex life, but also I want to have a sex life that feels more full and varied. We talked about it recently and my husband was clearly very worried and feeling vulnerable. He is such a lovely, open person. He expressed that he has never really felt confident with vaginal sex, and puts it down to starting to have sex a bit later in life. He had other partners before me, but I think still feels like he doesn’t have a great range of experience. I think this problem isn’t particular to our relationship. I don’t want him to feel like it’s all his fault. I feel guilty and upset about this, and I just want it to work, but I don’t know what else I can do.

What would you advise?

Universal Serial Bang

DEAR UNIVERSAL SERIAL BANG: Alright USB, there’s a two-part solution to this problem. But first, let’s make sure we’re solving the right problem. So before I dig into what you and your husband can do, I want to ask you: is the problem his getting off, or is it how he feels about it?  You say that you can’t make penetrative sex work, and that he can’t get off except by masturbation, but that leaves a lot of unanswered questions about what that means. Is the issue that your husband is frustrated with not being able to orgasm during PIV and this makes it difficult to stay hard or remain engaged with you during penetration? Are you feeling the pressure to get him off during sex and that tension is interfering with your ability to enjoy sex with him? Is this a case of “it doesn’t count if he doesn’t have a ‘look-ma-no-hands’ orgasm in your hoo-hah” for one or the both of you? Or is it that he feels like not being able to get off during PIV makes him feel emasculated and that makes him less interested in sex in general? 

I ask because the nature of the issue changes whether this is actually a problem or just an unorthodox set of circumstances. If, for example, he’s totally cool with what he currently needs in order to climax, then this isn’t necessarily a problem so much as need to change how you two define sex and change up the way you’re intimate together. If, for example, he can stay hard during penetration to give you the kind of pounding you desire and then you can give him a handy when it’s his turn, then all you really need to do is adjust your expectations around what sex looks like in your relationship.

But if it’s bothering him, or you, or both of you and that discomfort is affecting your mutual willingness or desire to have sex… well, there’re a couple things to be done.

The first is to deal with the ahem root of the issue.

If the only way he can reliably get off during sex is through a hand-job with a very particular level of pressure and pattern of speed, intensity and stimulation, then yes, it’s probably a result of what doctors call “idiosyncratic masturbatory technique” – the dreaded “death grip” syndrome.

Because of the ways that some men discover masturbation, it’s possible for them to functionally train themselves to require levels of pressure and friction that human orifices simply can’t replicate. For some men, they discover masturbation by rubbing up against a pillow, sandwiching their penis between the mattress and box spring or the cushions on the couch. Others have more of a ‘grip it and rip it’ technique, where they simply are squeezing their penis much harder than they would experience from partnered sex. As a result: they’ve carved a groove in their brain where the level of sensation they need is very specific, and it becomes incredibly difficult to actually climax without it.

Now, the good news is that this is fixable. The bad news is that fixing it is a literal exercise in frustration; your husband would need to be willing to practice a very specific form of orgasm denial while he’s retraining himself. It comes down to having to starve himself of the required sensation – in other words, no masturbating, no hand jobs, nothin’ – until he’s so pent up and desperate to orgasm that the less-intense sensations of penetrative sex will get him there. If he can’t get off from penetration, he just doesn’t get off.

That, unfortunately, can take time and it requires some pretty significant dedication to not fall off the metaphorical wagon. If he’s already a bit averse to having PIV sex because of his condition, then he may still struggle to be motivated to have sex. A masturbation sleeve that’s more akin to the human body – such as one from Tenga or Fleshlight – might be an option for helping to retrain himself if he feels too awkward or self-conscious about sex with you.

Now that having been said, that doesn’t mean that you and he can’t still have penetrative sex while he’s retraining himself. In fact, this is an opportunity for the two of you to expand your sexual repertoire about what sex is for the two of you.

You’ve mentioned how this has been frustrating for you as well, especially since the way that he has been able to get off required positions and angles that don’t work well for you. One of the options for the two of you, both while he’s working on the issue and in general – is to start incorporating toys into sex. A penetration toy of some sort can give you the kind of sex you want and need without needing to worry about performance issues from your husband. There are a number of options that you two could experiment with, including ones that would allow you to have the sort of thrusting and positions that you like. There are strap ons, for example, that seat the dildo on the wearer’s pubic bone, allowing for the wearer to thrust and grind with their hips as though they were having standard penetrative sex. There are also ones that could be strapped to one’s thigh, so that you could sit on it and ride it and get the precise angles you need.

The important thing, however, is for the two of you to actually talk things through. I understand your hesitancy and his; this is an issue that can strike pretty deeply into male insecurities on his part, and you don’t want to make things worse by making him feel like he’s letting you down. But by not talking things through, thoroughly, all that ends up happening is that nothing gets resolved. He still ends up feeling weird and uncomfortable with the situation, your needs continue to not be met and nobody benefits.

Talking about it, however, doesn’t mean that it’s going to be an uncomfortable or upsetting experience. The key is that this isn’t about someone’s inadequacies or failure, it’s about the two of you collaborating together to solve an issue in a way that will benefit the both of you. Focusing on the fact that this is about the two of you coming together (er… as it were) to solve a problem and recognizing how this will not just fix the issue at hand but make your relationship better, stronger and more satisfying overall. It’s the sort of joint effort that brings you closer together, because you’re reaffirming that it’s not about who’s satisfying whom, it’s that you’re a team and you’re in this together.

Now understanding that intellectually doesn’t necessarily make it easier to have that conversation. It may be helpful to have a sex therapist or sex-positive couple’s counselor facilitate the discussion. Seeing a counselor together can help the both of you express yourselves to one another in ways that don’t feel accusatory or like a stab at one’s ego. If you don’t have a counselor you feel like you can go to, the American Association of Sexuality Educators, Counselors and Therapists has a referral directory to help you find someone in your area.

Again: if the both of you don’t treat this as a failing on his part but instead as a way to find options that work specifically for the two of you and your unique relationship, then it feels far less threatening and much more affirming. You would be encouraging him to feel empowered to open up and be vulnerable by showing him that he can trust you not to judge him or otherwise “punish” him for opening up, while he has active steps to take that will help you both while also getting positive validation and affirmation from you.

So talk things through – with someone to be your conversational Sherpa if need be – and collaborate on the solutions. It’ll make things much better for the both of you.  

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 have an ex-girlfriend who I’ve since maintained a friendship with. When we broke up, it was tenuous as break ups often are, but we both saw it coming and ended things amicably not long after.

After our initial breakup, we had an on-again off-again friends-with-benefits arrangement, partially at her behest. It petered out after a while, not for any particular reason, just that we needed space from each other.

Recently we’ve gotten back in touch as friends again, and it’s actually been pretty nice. However, I can’t lie, it would be nice to broach the FWB thing again. She’s said a few things here and there that give me the impression she’d be game for it too.

My problem is that I’m not sure if I’m just looking for those signs cause I want them to be there, or if it is a mutual desire. I love being friends with her, and I genuinely don’t want to ruin that.

Is there a mature way I can bring up the subject with her without it causing any issues?

I can take no for an answer, I just don’t want her thinking I’m only using this friendship for sex.

Friends With Benefits Package

DEAR FRIENDS WITH BENEFITS PACKAGE: It’s good that you’re aware that the signs you’re seeing might be dickful thinking, FWBP. Motivated reasoning is a motherf--ker and when you really want a particular outcome, it’s easy to turn even the most innocuous thing into a “sign”. Similarly, it’s easy to overlook or dismiss signs to the contrary or rationalize them away because at the end of the day, you don’t want it to be true. So when you think you’re picking up on “hints” or frustratingly vague “signs”, it could well be that you’re rounding things up to the result you want simply because you really want it.

So let’s break down how you can tell whether or not this is actually a thing, or if you’re just really horny. And so the first step is that I want to flip things around and ask you a question: when you and your ex decided to try being friends with benefits, how did it happen? After all, you’ve already done this once before, so examining past performances can give you an insight into future expectations. So what lead to you two giving it a go?

Was there this lingering sexual tension between the two of you that you could cut with a knife? Were the two of you constantly finding moments where you were standing so close that you could slip one, maybe two but not three pieces of paper between your lips? Did you keep having instances where a hug started to linger too long, a friendly kiss hello or goodbye seemed to be longer or more intense than expected? Did friendly conversation turn first to innocent flirting and then become increasingly less innocent?

Or was it more matter-of-fact? Was it a conversation where someone brought up the possibility and you both agreed that it sounded like a good idea?  Was it something that you all explicitly talked out, rather than the old chemistry continuing to burn hot and strong, relationship-suitability be damned?

The point of this exercise isn’t “if you’re not having to hold yourselves back from jumping each other’s bones, don’t bother”, it’s to compare how things proceeded back then with what you think you may be seeing now. If there’s a significant difference between then and now, then the odds are higher that this may be in your head (and pants) rather than in the air. That isn’t a guarantee, one way or the other; after all, this is would be your third go-round and you’re not the same people you were the last time you decided to start bangin’ again. But it least gives you a metric for you to measure the current relationship against.

It’s also good to compare those hints to what you know of your friend. If she’s not the sort of person who’s willing to just put it out there and was more subtle or talked around it the first time, then it’s more likely that she might be hinting at things this time. But if it was a more open or more obvious lead-up compared to now, then I’d put money on your hornt up imagination doing some creative editing.

The next thing to consider is why you stopped being FWBs last time. You say that there wasn’t any particular reason outside of needing space, but what did that look like? Was the steam running out of your hot and steamy hookups? Was it a case that the chemistry had always been there but the little frictions and irritations that happen in every relationship drive you apart? Did your dynamic fall back into the same pattern that you had when you were dating, leading to a second, less significant break-up? Did either of you start having second thoughts or feel like maybe this was keeping you two from moving on and seeing other people? Or is it possible that one or the both of you were just done?

Just as importantly: have things changed between you in such a way that would also mean that the reason you stopped being FWBs no longer apply?

Much like when deciding whether or not you should try to get back together with your ex, if the reasons why you stopped the “benefits” part of the FWB haven’t changed, then proposing you pick it back up again is likely not going to work. Even if she is feeling it, you’re going to end up right back where you were the first time – just a little faster this time around.

And the last thing I would ask is: are you hoping to revive the FWB with her because you two have this undeniable chemistry, even if you don’t work in a more committed relationship… or are you just horny and she’s convenient?

Now I know all of this sounds like I’m trying to lead you to giving up on the idea and I’m really not. I’m asking you to really interrogate what you’re feeling and what you think you’re picking up from your friend. Part of improving your social calibration is being mindful of what’s actually there – even if it’s subtle – and what’s just your brain trying to make it happen at all costs. You’ll save yourself an uncomfortable conversation if, after digging in, you realize that maybe you’re just hoping for something, rather than picking up on hints and signals.    

But the person who knows for sure whether or not she’d be into it is your friend. And presumably she knows you well enough to know that you’re actually her friend in good faith, rather than someone who’s hanging around to try to get in her pants one more time. If you’ve made it through a break-up and an FWB phase and you’re still close? You should be able to say “hey, do you ever think of trying being friends with benefits again? I’d been thinking about it recently, and I was wondering if you might be interested in giving it another try,” without worrying that she’s going to make unwarranted assumptions about your intent.

By the same token, you should feel comfortable enough to say “It’s totally fine if you’re not interested,” and hopefully she feels comfortable and secure enough in the friendship to give an honest answer if she isn’t. And if it does shake out that she isn’t feeling it? It may be awkward for a hot second, but you’ve come out of far more awkward moments before and you’re still good friends. Any awkwardness will be temporary and inconsequential, especially against the backdrop of your current friendship.

So take a little time to examine things first. Then, if you’re genuinely sure that there is some mutual interest, ask. Focus on being clear with your intent and interest more than trying to find the magic way to thread the needle; the more you try to dress it up to avoid awkwardness, the more you sacrifice understanding in the name of not making it uncomfortable.

Good luck.

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