DEAR DR. NERDLOVE: My husband and I’ve been together for many years now (married three, together seven) and while we’ve both been somewhat vanilla our whole lives, we’ve decided that our sex lives have gotten a little boring and routine and we’ve been branching out to spice things up. 

In addition to a lot of the usual advice about date nights and breaking up old routines, we’ve decided we’re both interested in threesomes. After a lot of talking about it, fantasizing about it and just getting each other turned on about the idea, we’ve started actually taking steps to make it happen. We’ve got a joint account on a couple of specific apps and we’ve made tentative overtures to some friends of ours who we suspect that would be into it. 

Now we have a couple of likely candidates and while I’m incredibly excited for this to happen, the reality of it is making me nervous. What if our lucky third decides they like one of us more than the other? How do I keep from getting jealous or freaking out watching someone else getting that intimate with my husband? What is the etiquette for afterwards? Do we just hand them a towel and a bottle of water and say “see you?” Is it ok to see a third individually as well as together? 

I’m looking forward to this, but I’m also starting to get the jitters too. We both want this to happen and not be a huge mistake. What do we do? 

Three’s A Party

DEAR THREE’S A PARTY: Before I get to the actual advice part of this, let me congratulate you and your husband on not just freaking out about your sex life going the way that pretty much all relationships, but taking steps to keep the sexy adventures going. Trying new things, taking risks and not falling for the trap that marriage and settling down is the end of adventure and exploration are all part of how you keep a long term relationship strong and vibrant.

Now when it comes to threesomes, you want to take things carefully. There’re a lot of mistakes that couples make by accident in no small part because, quite frankly, their ideas about threesomes come from porn, where they just “happen”. When you have a script and a director, it’s a lot easier for things to be “spontaneous” because the eventual outcomes are baked in. In the real world, this has the potential to blow up in your faces – and not in the fun, sweaty ways you’re hoping for.

One of the biggest issues is simply finding that guest star. My general advice if you are looking for a third is to start with exes that you’re on good terms with. Because there’s that pre-existing relationship with them, they’re a known quantity, and it’s often easier to discuss boundaries and limits and what to expect than it is with someone you just met at a bar or on an app. The chemistry you (or your husband) have with the ex also helps with any initial awkwardness and smooths over the potential for someone pulling a move that the other person just doesn’t care for.

My second choice would be to hire a sex worker to be your third, rather than going to the apps. Mixed-gender couples have an easier time hiring someone than finding a potential unicorn, even on apps designed specifically for kink, polyamory, group sex and so on.

(Gay and bi men tend to have an easier time finding thirds simply because it’s easier for people who sleep with men to find someone who’s down to clown.) 

Hiring an independent escort cuts out a lot of the worry, simply because they’re there to perform a service and leave when everything is done. It can often feel a lot easier to talk about expectations or who gets how much attention when the third is there to play a specific role, whereas telling a stranger – or even a friend – what is or isn’t on the table can feel uncomfortable and awkward. The fact that the sex worker is there to do a job also cuts down on any post-coital anxiety like “will this person be a threat to our relationship” or “what do we do if we see them in public?” or any of the other common worries.

The next thing is making sure that you, your husband and your potential guest not just have chemistry, but that you are all on the same page regarding things like testing and safety, boundaries and so on. If your guest for your upcoming threesome is from the apps, then I’d recommend that you, your husband and your potential guest star meet up on a date for a vibe check – and this part is crucial – on a day when you are not going to go back and f--k. You want to get a feel for whether the three of you will vibe together, whether there’s chemistry and if all of you are going to play well together. Considering the potential stakes, you want to do this when you have time to let things percolate, rather than feeling the pressure of “well, we’re gonna do this tonight, so let’s get through this part and get straight to it.”

Part of this due diligence meeting should be about laying some ground rules – ones that you and your husband should work out between yourselves in advance. One of the things that often helps people who are having a bout of nerves before their first threesome is to have some guidelines about what is or isn’t permitted with the third. This includes what you both expect: is this supposed to be your husband and your guest star lavishing all the attention on you, on your husband, both of you teaming up on the guest, or what. Being up front about what you expect, how you want it to play out and what is and isn’t permitted (and for whom) takes away a lot of the uncertainty and worry. It’s a lot easier to relax and be in the moment when you know what to expect, rather than assuming it’ll all be fine and getting an unpleasant surprise at the worst possible moment.

One rule of thumb that’s often helpful is to take full penetration off the table entirely and just let your first time together be an extended makeout session. It’s a lot easier to process any weird feelings about seeing someone going down on your husband (or your husband seeing them going to town on you) when you know there’re limits and lines that aren’t going to be crossed. If all of you have a good time and you’re amenable to another date, then you can escalate things.

I’d still recommend that penetration be off the table (or at least, reserved for you and your husband as the couple in this scenario) until you’re both sure you’re going to be ok with it. This may mean a couple of play dates before y’all are ready to share; that’s fine. It’s better to take things slow and let the excitement build than to go all gas, no brakes and deal with the potential repercussions when someone suddenly gets in their feels about things.

Speaking of which: there is almost always a part in threesomes where it becomes a twosome for a bit. It’s as much about logistics and the limits of who’s got how many bits and the ability to multitask as it is about one person REALLY getting into the other. Ideally this happens in such a way that everyone feels like they’re getting roughly equitable amounts of attention, but that’s hard to organize in the moment. It’s important to a) realize that this is likely to happen and b) not to freak out about it. You don’t necessarily want to insist that they include you (or you two include the other) immediately, but also you don’t want to let it go on for so long that folks start feeling hurt or neglected or left out. If one person is feeling left out, it’s ok to gently say “hey, don’t forget I’m here…” and let things get centered as a threesome instead of a couple with a third wheel in the room.

I would also say that whatever rules and boundaries you agree to in advance are sacrosanct. There is no changing them in the middle of things, no matter what. Doing so is a very good way of guaranteeing that someone is going to get upset, even if it feels like a good idea at the time. If, in the middle, y’all decide that you would like penetration to be an option, plan a follow-up date where it’ll be allowed. Otherwise, you all have a plan and there should be no changes from what is or isn’t allowed.

On the night of, I’d recommend keeping drinks and intoxicants to a minimum. Leaving aside potential performance issues and the risk of someone being too intoxicated to give meaningful consent, staying sober helps prevent you from making some poor choices in the moment. People tend to make a lot of dumb calls when sex is involved. Don’t up the risk by having impaired judgement on top of all the f--k chemicals surging.  

Another thing to work out in advance is how you’re going to handle things afterwards. One of the worst things that can happen in a threesome is when the couple treats the third like a toy instead of a person. While I know it can feel a bit awkward in the post-orgasmic clarity, you don’t want to just hand them their clothes and push them to the door. This is a horrible thing to do to a friend or a stranger. I’d recommend having a plan in advance about what happens afterwards and making the arrangements in advance. An ex, for example, might stay over in the guest room, if you have one. Or you may all agree to get a hotel room so you don’t necessarily have the awkwardness of a stranger in your space. Again, these are things you should discuss with the third when you’re having your vibe check date, so that this doesn’t come as a surprise afterwards and someone gets the short end of the stick as everyone scrambles to figure out what to do now.

Consider how you would want to be treated if you were the third. At the bare minimum, I’d recommend factoring some time to clean up, decompress, maybe have a snack and some water before calling it a night and calling them an Uber or making up the couch (or possibly letting them have the hotel room while you head home).

Even if you’re hiring a sex worker to be your guest – where the entire point is to come and go – they’re still a person, not a robot. Being courteous, considerate and respectful is important. And be sure to tip well; it’s just polite and it’ll help for a better client/provider relationship if you decide to hire them again in the future.

You don’t say if you’re poly or non-monogamous or not, so I would err on the side of not playing separately, either before or afterwards. If, after a successful threesome, you or your husband talk things through and agree, that’s one thing. But if you don’t already have a baseline of experience with non-monogamy, I’d suggest holding off; the risks of someone tripping over their junk and causing problems is just too high.

Now I know this sounds like a lot of groundwork in advance of what is supposed to be a fun adventure, but trust me: preparation makes everything better. It’s a lot easier to relax into the moment and enjoy things when you don’t have that nagging voice of anxiety in the back of your skull or the uncertainty of how to handle X, Y or Z. The more you take care of in advance, the more fun you can have when the time comes, simply because you don’t have to think about it.  

Oh and one more thing: one of the issues people often run into when they’re planning a threesome or a swap or other group sex activities is actually getting things started. If you find that you all are standing around talking and not actually doing anything, I’d recommend using the magic words “Hey, I’ve got an idea…” and then suggesting either that the clothes start coming off or you all adjourn to the bedroom.

Good luck.

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

DEAR DR. NERDLOVE: Last year, my girlfriend of six years and I broke up. That’s not why I’m writing though. She had to move across the country to take care of her aging family, I can’t move because I have too many obligations here and neither of us can do long distance and so we decided to end it while we still loved each other. It was as healthy and friendly a break up as you could want but it still hurt and it took me some time to recover. Now I find myself in a really odd place, emotionally. While I can say I’m well and truly over the break up, I think I’m afraid to actually date again. 

It’s not that I don’t think I’m attractive or that I couldn’t find someone. I know for a fact that I can attract someone in the short term. It’s that I’m afraid that I won’t be able to find someone who could put up with me and all my weird little habits and lifestyle needs. To give an example, I’ve got a sensitive stomach and lots of things will send me running to the bathroom with very little warning. Who’s going to want to date someone long-term who’s going to have to poop six or seven times a day at random intervals? Or there’s my sleep routine: melatonin gummy, mouth tape, specific memory foam pillow, white noise generator, fan on and air conditioning going, otherwise I will be up all night and miserable the next day. Or any of a number of other weird little things that just seem like they’d be too much for anyone who might want a serious relationship with me. 

I don’t want to live the rest of my life like a priest or a monk, but the idea of someone learning about all my weirdness and deciding that they can’t make a life with me after all literally makes me wake up at night in a cold sweat. 

Any ideas about what I should do? Do I need to start forcing myself to rawdog sleep and a rigorous eating schedule to avoid embarrassing myself with trying to find a men’s room at the last minute? 

Freak Like Me

DEAR FREAK LIKE ME: Let’s leave aside things like “have you been to the doctor about your gastric problems” and instead, FLM, let me tell you a story.

In the Before Times, the Long Long Ago, I was out on a first date with a woman – someone I had a crush on for quite some time – and I was very invested in making this work. Which of course, meant that I might as well have directly invoked Loki, Coyote, Anansi, Eris and Sun Wukong all at the same time and told them that they were s--t at their job.

The date as planned was pretty prosaic – literally dinner and a movie, with a brief interlude between for a sappily romantic ride on a carousel. Well, five seconds after having sat down on the carousel horse, dinner decided to come back to haunt me. A couple very loud warning gurgles later and I immediately have to hop off and make my way – gingerly but at speed – to the nearest men’s room. It was, to put it mildly, a very near thing. And naturally because the universe works by fairy tale logic, I would leave the bathroom, head back to the carousel and then a VERY loud gurgle would announce that no, dinner was not in fact done with me two more times. So my date would see me emerge from the men’s room, be half-way back to the carousel, before I would immediately turn around and race back to the bathroom.

Twice.

And then the faucet on the sink burst and sprayed water down my front.

Things could not have possibly gone worse and the level of cringe set off seismic detectors in Beijing.

The movie wasn’t great, either.

My date and I were together for four years after that.

I bring that up because, by all rights, this should’ve ended the date right then and there. This wasn’t even a “ok, we’ve been dating for a year and now I’m comfortable enough for you to see this side of me”, it was the first time she and I had ever been out in a romantic context after nearly a year of my pining for her. This wasn’t my worst first date but it was pretty damn close.

But it still  worked out.

As it turns out, when someone likes you, it’s pretty hard to turn them off, especially if you don’t treat those things like a world-ending disaster.

Here’s the thing: you’re putting the cart way before the horse. The horse isn’t even in the same county as you right now. You are worried about things that aren’t going to be an issue for quite some time. You’re not – or at least I hope you’re not – going to leap from being single to shacking up with someone with no in-between. You’re going to have a pretty standard courtship period, and a lot of these issues simply aren’t going to be A Thing for a while. By the time any of it is actually going to be an issue, you’ll have had a decent amount of time together and you’ll be in the grip of New Relationship Energy. Let me tell you, the golden haze of NRE obscures many, many sins and makes all sorts of things little quirks and cute little idiosyncrasies. By the time the NRE fades, those oddities are going to just be Part Of Who You Are, and not nearly as much of a problem as you think.

But what about before you reach that point? Well, like I said: if someone likes you, they’re willing to roll with a lot of stuff. I’ve dated quite a few people with all sorts of quirks of their own, things that could be seen as being anywhere on the spectrum from cute and eccentric to legitimately limiting – from lifestyle choices to chronic conditions to “I have a very short list of foods that won’t kill me” – and none of them have been so egregious that I didn’t want to date them. The same goes the other way, too; I’ve got my own picadillos and oddities that can make living with me frustrating at times and it was never the deal breaker that I feared it would be.

(We had entirely different issues that would end the relationships, but that’s neither here nor there.)

And honestly, it doesn’t matter how supposedly “perfect” your partner is, there will absolutely be stuff about them that will make you grind your teeth with frustration at times. And they’ll feel the same about you. But you know what? While those things may make you roll your eyes to the heavens or grumble under your breath (and vice versa), they’re very rarely something that makes you say “Nope, deal breaker, I’m out” or “nope, can’t handle that”. Most of the time, you’ll just sigh and deal with it because as weird/outré/frustrating/inconvenient/genuine hard limits as it might be? They’re still them. They’re still the person you fell in love with and you’re still the person they fell in love with and those weird little things that make up your life are what make both of you uniquely yourselves.

Sure, there’ll be people who can’t roll with it. But that’s always going to be true… just as there’ll be people who won’t want to date you for other, entirely random reasons. There’ll be people who won’t want to date you because of the way you cut your hair or the smell of the product you use, just as there’ll be people who you will ultimately not want to date because of the way they pronounce aluminum or how they whistle through their teeth. But all any of that means is that someone who wasn’t right for you took themselves out of your dating pool, leaving you free to look for someone who is.

Those issues you mention may be a deal breaker for some. But for someone who’s right for you – and there are many who will be – they’re simply not going to be the problem you’re afraid they are.

We’re all f--king weird, we’ve all got quirks we think only a tiny, select few could tolerate and we’re all wrong about how big of a deal they actually are. Don’t worry about future problems that don’t exist. Just focus on meeting people who are right for you and you’ll be fine.

Good luck.

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

DEAR DR. NERDLOVE: I’m writing in to get advice about how to conquer my mindset, which I know is both unhealthy and unhelpful. I’m not entirely sure what question I am trying to answer here, so I’m praying you’ll have better insight into this than I do.

Ultimately, I feel that I have an obsession with the topic of dating.

Every day, from the moment I wake up to the moment I go to bed, there are many times throughout where I struggle to shift my thoughts away from the subject. I find myself reading a lot of advice columns, or perusing Reddit to see what people have to share about their experiences, only to find myself thinking back to my own life and ending up stuck in rumination and over-analyzing events, to the point it can consume much of my day. While I partly attribute this to my friends and family always inquiring about my love life and thus reminding me on a regular basis, fundamentally it’s become a habit to “go down the rabbit hole” with this way of thinking.

I’ll give you an example. Today I happened across a thread on Reddit about “missed hints from women”. I’ve never been able to determine if a woman is interested in me, but in hindsight I thought back to moments where this may have been the case. I also started fantasizing about the prospect of a woman showing interest, in some made up scenario or perhaps based on what I had been reading. So I’m sat there with this thread open, getting lost in thought, and…boom…two hours have gone by.

Now, don’t get me wrong – my entire life doesn’t revolve around trying to get laid or finding a relationship, as I know there’s people out there whose every living, breathing moment is centered around trying to get notches on their bedpost or finding true love. I’m not actively dating and haven’t been on one for thirteen years. My lifestyle isn’t adjusted or governed in any way in an attempt to find someone. I’m quite fulfilled and successful, so in theory there’s no reason why I couldn’t be someone’s lover, but I’m not here today looking for advice on how to date.

If I were to try and answer my own question, I’d say it’s me being overwhelmed with the knowledge of having not been able to experience this part of life, and not being able to accept the idea that I could ever do so. FOMO? Whenever I read these discussions online, or listen to friends talk, I can’t relate to these stories of having met a potential partner at a house party, or being in the “talking stage” with someone they met online, or that brief sexual encounter while on holiday. How does one even get to this point? Talk to people? I do that and nothing happens. And there we go, the cycle of over-thinking has now begun. It all feels so alien to me. Perhaps I am the alien. The very concept of these events is just not something I can wrap my head around.

I don’t think it’s having too adverse an effect on my life. Although I do feel lonely at times (naturally), I simply get on with things. My realization today was that I’ve been engaged in this habit since I was 18, and I just don’t want to reach my 80’s with these thoughts stuck in my head all the time.

Broken Record

DEAR BROKEN RECORD: As someone who is professionally obsessed with dating, this isn’t exactly a mystery, BR. In fact, it’s kind of obvious what’s going on.

When we get hung up on a particular topic like this, to the point of near obsession, there’s always a reason. It’s a little like someone with an anxiety condition who doom-scrolls through worst-case scenarios and reads up about disasters. You would think that someone who is always afraid of the worst happening would want to avoid thinking about it, not marinating in the topic… except that’s not why they do it. To them, reading about the worst that could happen is almost a relief, a way of easing that anxiety. It’s almost literal magical thinking – focus on the worst and it won’t happen – but it brings an ease with it.

This behavior is an adaptation to a particular need, the mental equivalent of dealing with a persistent itch. Indulging in it like this is, functionally, scratching the itch. You have a mental itch, and reading subreddits or dating advice columns, indulging in those daydreams and so on make the itch go away.

The problem is that, like actual itches, scratching it doesn’t actually make the itch go away. It just overwhelms the nerves so that you don’t feel it for a little while, before it comes roaring back. What’s also significant is how much the resurgence makes the itch worse, because this behavior doesn’t actually fix the underlying issue. It’s your brain trying to resolve discomfort, but doing so in a way that no longer meets your need.

So the first step is to pay attention to the need that your brain is trying to meet. And to be perfectly honest, I don’t think your analysis is right. I don’t think this is about being overwhelmed by anything, nor do I think it’s FOMO. The fact that you’ve been doing this since you were 18 is the key that unlocks this particular mystery. This is straight analysis paralysis and has been for a long, long time.

Were I to hazard a guess, what I suspect happened is very simple: like a lot of 18 year olds, you wanted to date but a combination of anxiety, unfamiliarity and frustration lead you to try to figure out what x-factor was missing or what you needed to learn in order to date. The problem is that if you ask five people questions online about dating, you’re going to get six opinions and there’s a part of you that feared rejection far more than you feared being single. So, again, like a lot of people, especially young people, you decided research was the answer. Research and study would eventually lead you to the magic formula that would lead to perfect success with no risk.

The problem with this, as any author will tell you, is that research is not the same as action. It feels like action, because you’re actively doing something that you tell yourself is going to make the end result better. But what it doesn’t do is actually move you forward. The author who gets stuck doing tons and tons of research isn’t actually putting words down on paper, and the person who is constantly reading and studying about dating and reading subreddits and watching YouTube videos isn’t actually out there trying to date.

(And honestly, I don’t include dating apps as taking actual steps, for a lot of reasons. Like research, it’s the sort of thing that feels like you’re taking steps, but it’s very much the illusion of effort. Especially as the monetization strategies of the dating apps makes them increasingly less useful.)

The problem is that, as I said: dreaming isn’t the same as doing. Research isn’t the same as doing. Collecting the gear you “need” isn’t the same as doing. Neither is making a Pintrest board, visualizing or anything that isn’t actually going out and putting in the effort and – importantly – making a lot of mistakes. 

Because here’s the thing: the folks who succeed are the ones who didn’t spend all the time preparing and researching and studying. Preparation, research, study… that’s all good and important, don’t get me wrong. But they’re not the same as actually going out and f--king up. Your favorite artist has hundreds upon hundreds of drawings and paintings and illustrations that went straight into the trash. Your favorite writer has pages upon pages that will never see the light of day, novels that are stored away in a forgotten corner of their hard drive or shoved in a desk drawer. Musicians have s--tty songs, computer developers have oodles of spaghetti code and so on. The people who are successful at dating? They’re folks who’ve gotten rejected a lot, because they put themselves out there a lot.

Because anything worth doing is worth doing badly. Doing things badly, without trying to be perfect or avoid all mistakes is part of how we learn and grow. Trying to avoid errors and look for the critical path that will give us the magic formula or teach us everything we need and let us avoid the Pain Period ultimately leads nowhere. And analysis paralysis is precisely that: trying to avoid the pain period.

The thing is: do this for long enough and the task itself becomes the point. It’s still scratching the metaphorical itch – kind of – but the point of it has changed and mutated and now instead of being something that you’re doing for a supposed purpose, it’s become the thing you’re doing, end of. Find an excuse to put off doing a task for long enough and eventually you start just doing the excuse instead. You’re still scratching the itch, but scratching the itch has become the point.

In your case, that itch is still “wanting to date and to date successfully”. Reading those threads, falling down those rabbit holes and daydreaming about it are all ways of saying to yourself “ok, I could still do this if I wanted. I can still make this happen. I’m closing in on the exact steps I need to make this work”. There’s a part of you that’s still trying to find the magic formula that will make it all make sense, so you can step out of the house and say “3X2(9YZ)4A” and off you go. It may not be your conscious motivation anymore… but it’s still there.

So now that we’ve identified the need going unmet, the question becomes: what would be a better way to deal with this need? If you ask me – and you did – then I’d say the first thing is to start taking actual responsibility and recognize your agency in what you’re doing. You use a lot of passive language in your letter to describe what’s going on and I think that’s part of the problem. You didn’t find that thread through sheer happenstance, nor did it fling itself before your eyeballs while you were unable to resist. It didn’t appear on a billboard in Time’s Square or pop up on your smart TV. You were reading a dating subreddit. The same with reading advice columns or watching videos on the topic, etc. You’re making a series of decisions that lead to your going down these rabbit holes.

The way you describe it makes it sound as though these are less choices and more coming out of a fugue – as though you suddenly woke up and realized that Edward Hyde had been reading Dear Prudy before you shifted back to Dr. Jekyll. And they’re not. You’re the one deciding to chase that particular white rabbit down its hole. Start by acknowledging that you’re the one making these choices and remind yourself that you actually have agency.

Now, if you have truly made peace with never dating, I’d say that the answer is to just go cold turkey. Quit reading the advice columns, block those subreddits in your browsers and so on. Classic “Doc, it hurts when I do this”/”Ok so stop doing that.” But I don’t think you have. I think you’re resigned to it, but clearly you still want it. And my advice would be to echo a different doctor: don’t dream it, be it. Start working on your social skills, start practicing your flirting and start asking people out on dates. You don’t need to do all this research and all this trying to find the Rosetta Stone of dating, you need to go out and make mistakes. You need to go get rejected, brush yourself off and start again.

Because here’s the thing: despite what your anxiety tells you – and you’re not alone here – nobody really cares about how long it took you to get to the party, the point is that you got there. Nobody is dating your romantic history, they’re dating you. The only time the window is well and truly closed is when they’ve closed the box and lowered you into the ground.

Will this require adjustment? Sure. Will you need to upend your life a bit to make room? Well, yeah. That’s how it works. But it seems pretty clear to me that this is something you want, so perhaps it’s time to start actually trying again instead of trying to convince yourself that you don’t want it.

But that’s ultimately up to you. The choice is yours, one way or the other.

Good luck.

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