How Do I Find The Sex I Actually WANT?

Estimated reading time: 16 minutes

Hey Doc,

I find myself in a bit of a weird place. I’ve just ended a long stint as a caretaker for an ill parent, and with this newfound lease on life, I’ve been putting myself out there a lot over the past year looking for casual sex. And while I’m still a bit stumbling and awkward, I’m actually occasionally finding women who are interested in me! But it’s always been in situations that have made me wildly uncomfortable where I retroactively find myself wishing I hadn’t.

I’ll spare the full itemized list, but a few examples of the sort of thing I’m talking about: There was a time a group of regulars at a bar very kindly welcomed me into their circle, but when it came up that two of us were interested in each other, we kind of got thrown together and demanded to start fooling around for the group’s amusement, which I very quickly discovered was NOT my thing and kind of scared me off. There was a girl I met up with through a dating app, but the date suddenly started multi-track drifting right off the rails in the eleventh hour and I was already starting to feel on the fence about things. But I was dumb and horny and said yes anyway, and after getting pulled through a whirlwind couple minutes, I just kind of sat there with this sinking feeling of regret.

In the grand scheme of things, I understand that these examples are all fairly benign, common even, but the point is that I just have not been enjoying these experiences. Just bad times all around, man. The first few times, I just dusted myself off and moved on, but every time it happens again, I get a little more confused about what I actually want.

This, unfortunately, also maps to most of my experiences historically. In my blissfully dumb college years, I’d stumbled dick-first into just about every bad decision I could’ve in the name of sex — helping people cheat, getting back together with exes, getting over one girl by getting under her friend, just the full laundry list of every stupid game you could possibly play to win a stupid prize, and unsurprisingly, none of those were positive experiences! And when I got back out there this past year, a little older, wiser, and a lot more sure of what I wanted, I thought I could find casual sex without any of the moral compromises or uncomfortable situations I was used to attached, but here I am again. I just want to find sex I actually feel *good* about, where I can give that enthusiastic yes and not look back on it and feel regretful a day or a week or a month after.

I feel like the obvious answer here is that casual sex just isn’t for me and I should just go find a dedicated relationship, but I’m hesitating about whether that’s what I actually want, or if I’m even in the right place to try. The parent I was caring for just died a few months ago and I’m in the middle of a “career transition” if you catch my drift, so I’m already going through a time of great upheaval and I’m not really sure I want to add a relationship on top, or if it’s even a good idea. And I’m already blessed with a fantastic support network of multiple groups of friends, so I don’t even feel particularly lonely or in need of companionship. I’m just horny. And “getting into a committed relationship so I can get laid” feels like exactly the wrong kind of energy to enter into one with.

But the alternative, my attempts to dive into casual sex, have led me to a lot of places I just haven’t enjoyed, and at this point, I’m all spun around and need a reality check. Do I need to just get over myself? Do I just need to keep going, and eventually I’ll find what I’m looking for? Is there some other way I can be going about this? It feels like such a weird “first world” problem to have, but I really don’t know what to do about it.

Goldilocks

So, before I get into solutions for you, I just want to double-check with you whether the issue is that you want casual sex, or you feel like you’re supposed to want it? Because the two aren’t necessarily the same, especially seeing as how it seems to always blow up in your face. And not in the fun, sticky way.

Now, I ask, because there’re a lot of guys who have experiences similar to yours – they pursue no-strings sex with people they don’t really know (or like) because they feel like that’s what they’re supposed to want. They frequently have “reasons” why a casual hook-up or one-night stand is what they should be pursuing, but more often than not, the real reason is that they feel pressured to choose that option. Sometimes they’re trying to prove something – whether to an ex, themselves or even to society at large. Other times, it’s just that they feel pressured to go for something casual or without expectations, even if that’s not really what they want or need.

So while your list of reasons why you feel weird about possibly pursuing a more committed relationship are valid and understandable, it may be worth digging into them. Is that how you actually feel, or are those how you feel right now, and you’ll have different reasons a few months from now?

But let’s work from the position that you know yourself well enough to know that right now you can’t offer what someone might want in a more committed partner… but you still also want sex. The issue I think you’re bumping up against is that this isn’t a binary decision – either sex with randos that make you feel weird about yourself or committing to the long-term. There are options in between those two poles that might work better for you.

On one end of the spectrum, you might find that a casual relationship or friends-with-benefits relationship might work a bit better for you than a “relationship” per-se. Now, to be sure, both of these are relationships of a sort, but they don’t carry the same expectations of monogamy or long-term commitment. In both cases, the general idea is that you enjoy each other’s company and have plenty of sexual and physical chemistry, but neither of you are looking for anything more than “we hang out and we bang”. In both cases, you have more of a connection – you may not be seeing each other exclusively, but you’re also not just coming and going… er, as it were. This has the benefit of feeling less impersonal or mechanical, but doesn’t necessarily feel like either of you have the responsibilities that might come with a more committed relationship.

It also has the benefit that you and your friend/casual partner aren’t expecting this to go the distance. Most casual and FWB relationships tend to be short-term. With FWB relationships in particular, more often than not people either end the benefits aspect or they end the friendship.

(However, often “ending the friendship” actually means “they transition into a more committed, romantic relationship”, not “we stopped being friends.”)

However, just because your relationship is casual doesn’t mean that you can treat each other casually, nor does it mean that you can just coast along without needing to actually think about things or communicate with your partner. These are still relationships, and it’s important to at least have a defining-the-relationship talk where you make sure that you and your snugglebunny are on the same page about what you want, what you expect and what you’re available for. It’s also worth checking in with one another and making sure that the relationship is still meeting your needs and theirs.

On the other end of the spectrum would be to embrace short-term relationships – essentially, serial monogamy, but with the understanding that this isn’t a relationship that’s intended to last a lifetime. It may not even necessarily be a relationship intended to last more than a couple years, if that. A lot of folks tend to discount short-term relationships, especially a relationship that is short-term by design.

There’s a lot of cultural baggage around dating and relationships that longevity is the most important factor in determining a relationship’s importance, significance and emotional weight. That’s not the case. Just because a romantic connection didn’t last for years or end with one or both of you dying in the saddle doesn’t mean that it was meaningless or less valuable. The success or failure – or the meaning and import – of a relationship isn’t defined by length or longevity; it’s defined by the connection between the people involved, how they feel during and after and what they take away from it. A short term relationship that ends where you feel like you’ve had a strong and meaningful connection with someone, possibly learned things about yourself or discovered new things and still have affection and respect for one another is a resounding success to my mind. A relationship that curdled into mutual resentment but lasted until someone died, to me, is a failure, even if it “lasted” as long as it did.

Those options are open to you. However, regardless of which direction you may choose to take, you want to be mindful of what it is that you actually want and to communicate this to the people you might want to date or hook up with. Being clear about what you want and and what you can offer is vital. If, for example, you know you are going to want to see someone semi-regularly but can’t offer a more emotionally invested connection or more of a focus on your physical connection, then say so. Alternately, you may say that while you want to date someone and are willing to be monogamous, your life is in a shaky place and you can’t offer long-term commitment.

And when you do decide what you want and what you want to pursue, make sure that you stick to it. One of the reasons why a lot of women dislike “casual” relationships is that a lot of guys will blur the lines between “casual” and “committed” – expecting more of an emotional investment from their casual partners while still not offering commitment or monogamy. The whole “want a bang-maid” or “extruded relationship product” thing is real.

This doesn’t mean that you’re locked in forever. There may be a point where you realize you’re developing feelings for your casual partner or you’re starting to feel that maybe your FWB relationship is coming to an end and you want to move towards “romantic relationship”. But in those cases, you want to actually have a conversation about where things are going and what you want, not just hoping that you can kinda, sorta just fall into something without saying the words.

You don’t seem to suffer for finding casual sex, Goldilocks, which makes this a little easier. The skills are functionally the same. The difference is that, instead of just letting things happen, you approach things with a little more intentionality and mindfulness. Know what you want, so you can ask for what you want and things will proceed much more effectively.

Good luck.

Hi Doc,

Not sure if you’ve gotten these sorts of questions before, just found your site – but I have what I think might be a slightly different question from most.

I have a crush on someone at work, and I need to find a way to *stop* having it. Basically, there’s a woman my age in my department, and aside from being a really cool person in general, she’s one of those people that seems to just be naturally friendly and mildly flirty – nicknames and pet names over chats, leans on me sometimes when walking to lunch, asks me about my life outside of work, etc. I know this is mostly just how she acts, but the affection-starved mind goes “Maybe…?” And all of a sudden I find intrusive thoughts battering down the gates to my brain. This is inconvenient and undesirable for a few reasons.

First, I have to work with this girl near-daily in a small room with four other people. As much as our industry loves to present itself as having “laid back” company culture where we’re “all family” and whatever, I need to maintain at least some level of professionalism. Acting on any sort of feelings, mutual or not, would overcomplicate things, because real life isn’t an episode of the Office.

Second, I’m autistic – and while I’m pretty high functioning and high masking, I have a history of blowing these situations out of proportion or convincing myself I see possibilities that aren’t there. I’d rather not take that risk, even if I did think this was something more than just friendliness.

Third – I’m not even planning on being here much longer, as I have plans to go back to school in September in a different city, so what would the point even be?

All this to say, I would like to expunge these feelings. I’d like to avoid making my work life awkward and my social life embarrassing, because again, she’s a genuinely cool person I want to stay “work friends” with, but not so much I’d risk my job dynamic and my already fragile self-esteem, much less make her feel uncomfortable.

What’s your prescription?

Best,

Feelings F’in Suck

Not gonna lie, FFS, this sounds like a “who’re you trying to convince, me or you?” kind of situation to me. The way you lay things out sound to me like it’s less of an objective “it would be better if I didn’t feel this way” or “these feelings are a problem” so much as “I would want this but I don’t think I deserve it/it would never work out for me because REASONS”.  

I also wonder if part of the problem is that you spend a lot of time masking – and let’s be honest, masking is exhausting to maintain. A lot of times, I see autistic people who work themselves into knots trying to hide being autistic or trying to force themselves to operate like they’re neurotypical when it would be easier and better for them in the long run to stop and work with who they are. To be sure, there’s a lot of social pressure for neurodiverse folks to mask and perform as though their divergence didn’t exist… and I think that ends up contributing to the neurodivergent feeling that acknowledging their divergence as anything other than a negative is wrong somehow. Or that asking for accommodation is somehow worse or more taboo than needing to expend twice the effort to get the same results.

But hey, you know you and your life better than me, so what do you do about these inconvenient feelings? Well… the short version is that you treat her like a friend and let the rest be. The thing about inconvenient crushes and the like is that they’re like fire – if you feed them, they grow. If you just let them be, they burn down and eventually burn out. So a lot of dealing with a crush you’d rather not have is learning to not feed the crush – both with your effort but also your mental bandwidth.

Part of why a lot of people struggle with crushes and can’t get rid of them is that, as paradoxically as it sounds, they try to get rid of them. But what this does is have the opposite effect; trying to force those feelings away just makes them that much more present in front of mind. All you’re doing is the emotional equivalent of trying not to think of Rue McClanahan dressed as Bluey; actively trying to not think it means that it’s just going to pop up more and more.

If you keep trying to tell yourself it would never work for reasons X, Y, Z and Z3, then you’re ensuring that those feelings are going to stay right where they are. You’ll even have tasked part of your brain to start possibly trying to find a work-around for those feelings. But if, on the other hand, you just note and name those feelings – “ah, there’s my crush on $CO-WORKER” – and gently redirect your attention, you aren’t reinforcing them. You’re not shoving them away so much as just choosing to look elsewhere at something that actually needs your attention just then. That other thing will then take its rightful place and necessary bandwidth, which won’t be occupied by fifty different processes that all involve your coworker.

Now, another thing to pay attention to is how much you’re investing in the relationship – that is, how much time and effort you’re putting into your relationship with your coworker beyond what’s necessary for work. This includes reaching out to talk, make plans and so on… the sorts of behaviors one might have with a friend or partner, but not with someone who’s strictly a work friend.

One of the truisms of the human experience is that the more effort we put in for something, the more we end up wanting it. This is part of why, for example, online and service games will often emphasize the grind; the more you’re trying to grind for a specific reward or result, the more invested you’ll become in trying to get it. So while the game itself may have ceased to be fun for you, you’ll have sunk so much time and effort into it that you’ll have changed your priorities from “having fun” to “keep playing the game because I NEED this”.

The same is true for relationships. A lot of people ensure that they stay stuck in “The Friend Zone” (standard disclaimer: there is no Friend Zone) or in one-sided relationships because they keep watering a dead plant. The plant isn’t gonna grow, but they’ve invested so much time in watering it that they have a much harder time letting go of it or letting it not be a priority. If you’re putting a lot of effort in your relationship with her that goes beyond what you might for a casual friend or a coworker you don’t have a crush on, then you’re ultimately reinforcing your own emotional investment in her.

This is why another part of easing a crush is to dial things back and not put as much work into things. Now, this often can end up feeling like you’re pulling away from them and dialing back the connection you already have… and in fairness, that’s what you’re doing. But to someone who genuinely likes you and wants to be your friend… well, that can be hurtful. So it’s hard to do, on many levels. It takes a delicate hand, especially if you want to maintain an actual friendship with her.

But there’s one more thing about your letter that leapt out at me: you describe yourself as a “affection-starved mind”. I think that, in and of itself, is something that you really should be taking more of a look at for your own sake. I wonder, for example, if that this is another way you beat on yourself and tell yourself that you aren’t “allowed” to ponder the possibility or actually believe that maybe someone could actually be into you. While I don’t doubt that you feel starved for affection and connection – most men do, especially now – I wonder if that’s less of a symptom and more of you running yourself down instead.

I do think that, regardless of what ultimately happens here, you should pay attention to how you think of yourself and how you define yourself. There’re hints in your letter that make me think that you, like a lot of autistic folks, see the autism label as a demerit or disqualifier, rather than a neutral fact. It gets easy to say “no, I’m just being realistic”, but it’s a little like “brutal” honesty; the people who most pride themselves on being brutally honest tend to focus on the brutality rather than the honesty. Running yourself down and being relentlessly negative about yourself isn’t honesty or practicality or realism; it’s just good old-fashioned masochistic epistemology. So while you’re allowing this crush to fade… maybe it’s a good time to remind yourself that you’re allowed to have crushes and be attracted to people, to want to puruse relationships and to be open to the possibility that hey, sometimes people really do like you, and a relationship with them isn’t inherently a bad thing that you have to deny yourself.

Good luck.