This Is Why Dating Sucks for Everyone (and How To Fix It)

This Is Why Dating Sucks for Everyone (and How To Fix It)

Over the last couple of weeks, the Internet has been alive with the sounds of Discourse as multiple videos, TikToks, and columns have covered the latest Worst People In The World who are making dating a misery for everyone.

So… business as usual, then.

Whether it’s been the hosts of PUA podcast Fresh ‘n Fit losing their minds after getting bodied by Instagram model Brittany Renner and flipping tables over the idea that women have sex with dudes who aren’t him, or the antics (and subsequent doxxing) of Wes Elm Caleb, it’s been a bonanza of people yelling about the current state of dating. Arguments about what fits the definitions of lovebombing and gaslighting, whether ghosting is a The Sin That Can Never Be Forgiven or whether sex for men is like taking a piss have raged for days, alongside bemused takes memes about the chaos of it all.

Needless to say, it’s been a smorgasborg of relationship drama for folks like me; which trending topic should I share a hot take about first?

Spoiler alert… none of ’em, really. At least, not directly. To be honest, I’m not really interested in detailing and debunking shitty PUA podcast takes, nor am I interested in adjudicating anything about what West End Caleb did or if the fallout was out of proportion. Plenty of folks have covered all of that.

(Plus by the time this column goes up, there will be some new Main Character of the week and my attempt at blatant SEO juice will be laughably out of date.)

No, instead, what I am interested in is how much these incidents provide an illustration on just how dating has become an utter shitshow for everyone involved. In both of these incidents, we have amazing examples of not only toxic masculinity and believing the worst about men and women, but also how many barriers we put between ourselves, our desires and other people. So much of why dating has become a miserable slog comes about because of how often we get in our own way. The little tips, tricks and accepted wisdom we’ve all accumulated over the years seems like solid advice when, in reality, it only serves to make things harder for everyone.

So rather than join the chorus yelling about the Discourse DuJour, I’d like to talk about how we trip ourselves up and practices that make dating better – for ourselves and for others.

Stop Taking Advice From People Who Hate The Folks You Want to Date

You wouldn’t think this is something that needs to be said. And yet, here we are because – quite frankly – so much of what passes for “advice” in the dating sphere comes from people who apparently despise the very people they’re supposed to be dating. Hell, half the time, the people giving advice seem to despise themselves just as much.

screenshot from the Off The Record livestream; Brittany Renner sits across from Fit N Fresh hosts
Look, a dude who declares sex for men as being the same as taking a piss is basically telling on himself.

The appeal of podcasts like Fit and Fresh or subreddits like Real Female Dating Strategy isn’t advice so much as catharsis. It’s about having people tell you what you want to hear while also yelling at the folks who stubbornly insist on dating people who aren’t you. So much of the advice is a tell, revealing their own fears, angers and insecurities. Terms like “small dick energy” and “pick-meshas” get tossed around to create artificial in-group/outgroup divisions and provide a permission structure to not listen to dissenting voices. It’s the same self-aggrandizing in-group labeling as PUAs calling everyone else “AFCs” or “average frustrated chumps”.

(Also… Christ, “pick-meshas”? Really?)

It’s notable that the advice given by so many – whether from The Rules, The Game, r/seduction or any of the usual suspects – is centered around the idea of sex and dating as a competition. This creates a contentious, even combative framework. When you have a framework for relationships that have winners and losers you are, by definition, creating a situation where one person gets their desires fulfilled at the expense of someone else. This is, needless to say, a great way to set up bad sex and worse relationships. Advocating concepts like “last minute resistance” or how to “prove” a woman is lying about having a boyfriend aren’t about fostering connections but trying to not accept someone’s stated desire that they don’t want to fuck you.

The same applies to declarations about how to Be Alpha Bro, 1% men, Chads, Stacies and so on; this isn’t advice, so much as people trying to externalize their own insecurities. By declaring themselves to be Alphas/Omegas/Sigmas/whatever and You Can Too, they’re revealing more about themselves than they’re teaching self-development.

Animated gif of Tywin Lannister from Game of Thrones. Text reads: "Any man who must say 'I am the king' is no true king"

The truth is that this advice will never help. Half the time, it’s just a new skin over the same old talking points and same old, outdated “rules” around sex and gender roles that have no basis in either biology or reality. The advice that gets peddled will never address your real issues, it will never help you heal your trauma or overcome your phobias. It’s all slight of hand, a shoddy illusion designed just to confirm what you already believe and what you already fear. Trying to follow it – in as much as some of it can be followed – will only insure that your hookups and relationships will be toxic and filled with conflict and strife.

All relationships, even hook-ups and one night stands, are inherently collaborative exercises. They’re about two (or more) people building something together, not in competition with one another. When done right, everybody involved gets something from it and what’s built is bigger than the sum of its parts. This is the collaborative model of sex – treating sex like a jam session amongst musicians rather than a competition between opponents. You’re bringing your contribution to what others have brought in order to create a greater whole, not to just do your bit and leave like a hipster bro at a poetry reading.

hipster guy reading poetry in coffee shop
Seriously, there’re few people more obnoxious at the open mic than the dude who’s there to read his piece and leave without listening to everyone after him

But making dating more enjoyable and fulfilling for everyone goes beyond than just ignoring the haters, grifters and habitual line-steppers…

Know What You Want (And Own It)

It’s easy to assume that so many of our dating traumas come from shitty people doing deliberately shitty things. It’s nice to think that so much of why dating can suck comes from a small pool of assholes and if we could just excise them from polite society everything would be better.

screenshot from tiktok video about West End Caleb, purporting to be his hinge profile
“Ladies and Gentlemen… we got him.”

Unfortunately, reality is rarely so convenient and narratively satisfying. The truth is far messier and far less black and white. Not everyone who makes dating a nightmare is some mustache-twirling villain rubbing his hands over how he’s going to add another body to his arsenal. In fact, many of the headaches and heartaches that come with dating come from people who aren’t aware of the issues they cause. There are many, many people who are trying to date in good faith, but don’t realize what they’re doing. The problem is that many folks in the collective dating pool either have no idea what they’re looking for or – worse – are afraid to own it.

You’ve almost certainly seen this in action. Perhaps you’ve seen folks whose dating profiles run the entire gamut in terms of what they’re looking for. They’re down for hookups and long-term relationships, new friends and sexting partners, seemingly all at once. Now, to be perfectly fair: I’ve just described a solid 70% of the profiles on OKCupid. And, again, to be fair, it’s the sort of thing that seems kind of innocuous. Why wouldn’t you be open for any of those if they came your way? What’s wrong with someone being interested in a no-strings hook-up and looking for a committed relationship?

Well… because of the inherent contradictions involved. Are you looking for something committed or are you looking for someone to make 20 to 30 minutes of squeaky noises on Saturday night? Yes, it can be both – plenty of relationships start as one-night stands that just don’t end – but looking for both simultaneously can get in the way. There’s nothing wrong with being open to whatever comes your way and a charitable read would be that they’re open for all of these things. A slightly less charitable reading is that they’re not sure what they want and they’re trying to figure it out, which is precisely the problem.

(A third and less charitable reading is that they’re lying and only want hook-ups but want to create the illusion they’re open for more. More on that in a bit.)

The problem with casting your net quite this wide is that you run the risk of setting yourself up for confusion and mixed signals. If you’re someone who’s looking for a committed, long-term relationship and you go on a date with someone who has clicked all the “looking for” boxes, you might reasonably believe that they too are looking for something long-term. Except, after a lovely date that ends in good sex, you learn that while they may be open to commitment, they’re prioritizing something casual… something you only learn after you try to set up another date.

While they may not have actively lied or intentionally misled you, it’s still something incredibly frustrating. You thought you were meeting someone who was on the same page as you only to discover the truth after the fact. Even when there was no malicious intent and everything was safe and consensual, there’s still the gut-punch that comes with learning how mistaken you were.

Young man using smart phone and holding his head in pain at home.
Whomst among us haven’t had THAT conversation?

Most of the time, when people – especially but not exclusively men – say they’re open for everything, including long-term commitment, what they are saying is “I’m looking for something serious and committed… eventually.” And hey, that’s legit; nobody needs to go into every date assuming that this will be the last date will ever go on with a stranger. Unfortunately, most of the people who are looking for a long-term relationship are looking for someone else who also wants a relationship now, not down the line. They’re looking for somebody who’s on the same page as them, not somebody who’s dating around and figures that if they meet Mr/Ms/Mx Right, that’s a bonus not a goal.

As I said: there’s nothing wrong with being open to commitment if you find the right person. But if your current pursuit is “go on dates, see what’s out there and have fun,” then saying that you’re looking for long-term is misleading. You’re not looking for it now, you’re looking for it eventually. If that’s the case, then you want to say so, rather than letting folks believe that it’s something you want to find today. Dating is about where you are and what you want now, not where you’ll be later.

If you’re open the possibility of an LTR but don’t necessarily want one now, it’s far better, more honest and less confusing to focus on casual dating or short-term relationships. It’s much easier to go from a short term relationship to something more serious than it is to convince someone looking for exclusivity and a future to accept a casual relationship with no expectation of monogamy.

That same outlook applies to more than long-term and short-term relationships. If you’re someone who can’t or won’t do monogamy, you need to state that up front. In practice this means making it clear that you only want an open or non-monogamous relationship, not that you’re open to either. If you’re a kinkster or someone who needs a partner who’s into or up for non-standard-issue sex, that’s something you need to ask for up front and in your profile. Hiding it because you’re worried that it’ll affect your potential matches or that people will freak out and bail on the first date is a mistake. While it can suck to have someone decide to smokebomb out when they find out you’re into feet (or whatever), this is actually a good thing.

A smaller pool that consists entirely of folks who want what you want is far better than a huge pool of people who don’t. The former means that you’re dating people who crave the things you have to offer. The latter is a series of bad first dates and frustration for everybody.

animated gif of East Asian man in a ninjitsu uniform in an alley throwing down a smoke bomb and disappearing
“Oh, you’re into crypto…? NINJA VANISH!”

To be clear: there is an argument to be made – one I’ve made before, even – that leaving something divisive out of your public profile and bringing it up later isn’t the worst thing. In theory, it allows folks to get to know you as a person instead of the stereotype they picture when they hear about someone who’s kinky or non-monogamous or what-have-you. However, it’s very difficult for most folks to make that leap without leaving someone feeling tricked or mislead. As a rule of thumb, it’s far better to be up front and let the other person make an informed decision.

Similarly, there’s a difference between not knowing what you want at the time and hiding it. People do learn more about themselves as they go, and what you’re looking for or need can change as you learn more about yourself. However, if you go looking for things all at once, you tend to end up with bad matches. In general, if you’re not sure, it’s better to pursue the lower commitment options first. As I said: it’s much easier for a casual relationship to become serious, than to convince someone looking for a serious relationship to accept something else.

Embrace Honesty and Clarity

Here’s a lesson that most of us should’ve learned in Kindergarten: say what you mean and mean what you say.

Miscommunications and misunderstandings are among the most frustrating part of dating. We all have a tendency to assume that we’re all reading from the same handbook and playing by the same set of rules. It’s all too easy to think that our understanding  of the rules and definitions of terms are not only the correct ones, but that they’re universal.

Of course, this tends to fall apart as soon as you try to date in a new city or new community. There’re few dating rites of passage like the first time you run headlong into entirely different and unexpected “rules” around dating. Hell, half of the discourse surrounding West End Caleb has been “bruh, this is just dating in New York…”

Kristin Davis, Sarah Jessica Parker, Cynthia Nixon and Kim Catrall attend the German premiere of 'Sex And The City'
“They made two tv series’  about it and everything.”

But, West End Caleb is, in fact, a prime example of this. Leaving aside the allegations of sending non-consensual dick-pics (which is inexcusable), part of the conflict are the assumptions someone assuming that of course the othjer person would stop seeing other folks after going on a few dates. The problem is, nobody actually agreed to that. This lead to people getting caught off guard when it turned out they were the only person who expected that. It’s an easy assumption to make, in part because that’s what they wanted. It may even have been the norm in their social circles. But that doesn’t actually track to anyone outside that circle… certainly not without having actually having a discussion about it.

Honestly, it’s difficult to justify getting mad at someone for breaking an agreement that nobody told them that they were entering into. Not, mind you, that folks don’t try…

Kristin Davis, Sarah Jessica Parker, Cynthia Nixon and Kim Catrall attend the German premiere of 'Sex And The City'
“Seriously, it even got two movies. No, don’t watch them.”

However, for every good-faith misunderstanding or miscommunication, there’re also people who will deliberately use vague, unclear or misleading language to avoid clarity. Plenty of people go out of their way to allow people believe what they want to believe without actually lying; would-be Aes Sedai who try to surf the ambiguity wave and pull the “technically I didn’t say…” routine as their “get out of consequences free” card.

Here’s the thing: it doesn’t matter if you supposedly have the moral high-ground; that never means that people aren’t going to get pissed at you for misleading them. Technically correct may be the best kind of correct, but it’s never stopped people from being hurt because of wordplay fuckery.

If you want dating to suck less, then you need to focus on clarity and mutual understanding. In fact, you may need to do so to the point of bluntness and beating someone about the head and shoulders with a clue-by-four. In practice, this means saying what you actually mean in a clear and understandable manner, rather than talking around it or using colorful but confusing or misleading language. If you’re saying “yes” to something but what you say doesn’t actually include the words “yes”, “I agree”, “let’s do that” or something equally clear, you’re going to run the risk of being misunderstood. Don’t assume that your personal idiom or favorite phrase is as easily interpreted as you might expect; plenty of folks need to here a clear and explicit “yes”.

By that same token, you need to ask for clarity if you don’t understand  – again, to the point of bluntness, if need be. If you aren’t sure what they’re saying or you feel like they’re hedging their bets, you need to get comfortable with asking “what does that mean?” or “what does that look like to you?” If someone isn’t willing to be clarify what they mean or they refuse to give a straight answer, then you need to be willing to leave. Somebody who dodges direct questions or won’t give you a straight answer has a vested reason to prefer confusion to clarity, and it’s never in your benefit.

Upset woman hiding her face in her hands and man talking in cafe
“Look, I can’t help it if my incredibly evasive answers and constant deflections meant that you assumed things that I clearly wanted you to assume even though they were obviously not true…”

Of course, this means that you need to be willing to ask questions that you understand might mean you won’t see them again. I can’t tell you how many people I’ve worked with who’ve avoided asking important questions because they knew that just asking would jeopardize the relationship. The problem is that they prioritized avoiding the momentary discomfort of advocating for themselves over getting an answer they needed and, as a result, ended up in an awful relationship. If you’re afraid to ask for fear of not seeing them again, then that’s a sign you shouldn’t date them in the first place.

Unfortunately, this also means that it’s hard to justify being upset about a result you could’ve avoided if you actually did choose to use your words. Not that hard… but harder.

Part of the way you can bring more clarity to dating is to model the behavior you want from others and to be the change you’re hoping to see. That means being willing to state your intentions and needs. Not hint at, not imply and not ask: state clearly. Nobody is a mind-reader; if you’re afraid to say what you want or need, you’re never going to get it.

Now that having been said: it’s important to remember that you can’t prevent people from hearing only what they want to hear or even agreeing to your clearly stated goals or limits while they quietly think that they can change your mind. I’ve been on both sides of that equation on different occasions and it never ends well. Similarly, you can’t stop people from trying to wiggle around what you’ve said, no matter how clear and plain…

But you don’t need to make it easier for them either.

Take People As They Are (Instead of Getting Mad For Who They Aren’t)

Let’s talk about one of my personal pet-peeves when it comes to dating: getting mad at people because they’re not who you expect them to be… or who you think they should be.

Part of dating means accepting people as they actually are, rather than trying to mold them to your expectations. It doesn’t matter how universal you think your expectations are, nor how much better things would be for them if they would act just the way you want them to. Letting your expectations overrule their reality is a recipe for conflict and heartbreak.

Idina Menzel as Maureen and Freddi Walker as Joanne singing "Take Me or Leave Me" in Rent
I may have gone on a rant about this on Twitter the other day…

It’s one thing to get mad at someone becuase they break promises or act disrespectfully towards you. It’s another thing entirely to get mad at someone because of things that you’ve assigned to them without their consent, or even their knowledge. Doubly so if you’re getting mad about things that you knew about them from the start. Not even in the sense of “you knew I was a scorpion when you met me…” but about things that you thought would change in time.

The most obvious example is somebody’s sexuality. If, for example, you’re going to pursue a relationship with a kinkster, you can’t exactly be surprised when they want to do kinky shit. Similarly, if you’re dating someone who’s non-monogamous, you can’t be caught off guard when they persist in being non-monogamous. Demanding that they stop being who they are for you is a bad idea and – spoiler alert – it never works anyway.

However, it goes beyond obvious examples like sex. Some people, for example, aren’t prolific texters.


They may not always be online or always available, or they just may not be the type to get back to you right away. And while you can spend a lot of time and misery getting mad at someone for not being who you want them to be, accepting someone for who they are and adjusting your expectations accordingly will make your relationship a lot smoother. And if you can’t accept that part of them… well, nobody said you need to stay.

The same goes for other quirks, idiosyncrasies and bits that make somebody uniquely them. If you’re someone who thinks adults shouldn’t play video games or own stuffed animals, then hey: more power to you. You do you, superchief. However, that means you’re better to just not date someone who does those things. If you date them anyway or continue to date them after finding this out about them, then that’s a “you” problem, not a “them” problem and trying to force the issue is how you get both dumped and shared around Twitter as an Am I The Asshole post.

Nerdy Guy with an exploding Notebook
“Bruh, they’re roasting your ass in the QRTs…”

Yes, I know that you think this is a change they “should” make or that it’s something they “need”. It’s still a “you” problem. If they’re happy and their quirk or choice isn’t hurting others, then you can accept it or not as you see fit. However, you don’t get to force them to change. And if you can’t accept it or respect it… well, hey you know where the door is.

Nobody wants to be somebody else’s fixer-upper, especially if they don’t think they need fixing and didn’t ask for it in the first place. No matter what happens, they will not thank you, nor will they appreciate it when you try.

It’s very simple: you can take them for who they are. Or you can leave them.

Speaking of which…

Quit Chasing People Who Don’t Chase You Back

OK, let’s get the “but nobody chases me in the first place” responses out of the way so that we can move on to the actual point of this section.

Relationships – whether casual or committed, short term or long term – are group exercises. These require that everyone participate and while not every relationship is going to be perfectly equitable, it requires that everyone put in a genuine and sustained effort.

The problem is: a lot of times we find ourselves putting in most, if not all of the effort. Often without getting anything in return from everyone else.

Consider the times you’ve found yourself chasing after someone, but getting them out on a date – or even to reply to a text or DM – is like pulling teeth. Or the person who’ll agree to dates and get-togethers but always, always ghosts or cancels at the last minute. If you’ve experienced any of these, then you know exactly how heart-wrenching and frustrating it can be. It would be one thing if they just never responded; that would, at least, be a clear-cut sign. But what keeps the cycle going is that they never give that final moment that would set you free. Instead, you’re left like Charlie Brown, hoping that Lucy means it when she promises that won’t pull the football this time.

Look at those eyes. Black, like a doll’s eyes. She’s hoping to hear that sharp SNAP before the body goes ragdoll…

This isn’t even a phenomena that’s restricted to sexual or romantic relationships; plenty of folks have lopsided platonic friendships, where one person does all of the heavy emotional lifting and the other(s) just coast on giving just enough to keep the giver on the hook. They’ll give back the bare minimum – if that – but they also won’t cut ties or make it clear that they’re uninterested.

There’re any number of reasons why people do this. Some folks are playing “hard to get”, creating an artificial feeling of scarcity in order to keep someone on the hook until they’re ready to progress the relationship. Some get off on having “orbiters” – people who are always hanging around, hoping that some day they’ll actually come in contact with that particular heavenly body (and they won’t.) Others like to keep their options open and never fully cut things off because they might – might – decide that they’re bored and a blowjob would be nice tonight.  And still others want all the benefits of a  relationship, sexual or otherwise, without the attendant responsibilities and obligations that come with them.

The thing that all of them have in common is that none of them will ever be genuine partners. They’ll allow folks to live in false hope, even encourage it, but they’ll never invest in the relationship to any meaningful level beyond the absolute bare minimum. And sometimes not even then.

This behavior knows no gender nor sexual orientation. PUA and Red Pill gurus promote these techniques as “plate spinning”, while books like The Rules and dodgy subreddits encourage similar behavior so that women control and dictate the terms and pace of the relationship. Gay, straight or pan, cis, trans or non-binary… nobody is exempt from pulling this kind of shit, and, unfortunately, people buy into it all. THE. TIME.

Woman trying to kiss a man and he is rejecting her
Ah, the classic “Go away a little closer”. I know it well…

The reason why this technique works is that preys on other people’s insecurities. Call it the sunk cost fallacy, call it Oneitis, call it a scarcity mentality, hell call it “the only game in town”, but it relies on the other person being more afraid of confrontation or a break-up than being upset at being treated so disrespectfully.

As the sage said: a curious game. The only way to win is not to play. This is behavior that requires two people to participate, which is why the perpetrator will never give a clear sign that the relationship won’t happen; certainly not the way the other person hopes. The only way to break this cycle is to refuse to play along and just leave. Not “threaten to leave”, not “demand a discussion about the relationship,” or even to ask for more from them. It’s to accept that a dead plant is never going to grow no matter how much you water it and there is no amount of effort that’s going to turn this around. There’s been more ink spilled about how to get folks to quit playing games and actually commit and none of them work.

Here’s the truth. People who play games like this aren’t going to stop playing games just because you ask. Even if they decide that they’re “ready” and choose you, then staying in the relationship means signing up for even more stupid competitions for frame control and dominance within the relationship. Everything will be on their terms; your concerns, needs and wants will be secondary, if that. The only way to win is not to play at all.

This is why the single most powerful thing you can do is love yourself, to say “I may love you, but I love me more.” Loving yourself enough to not let someone screw with you is an act of power. It means that you’re willing  to be single, rather than to let someone jerk you around. And, just as importantly, it means that you won’t make the same mistake in the future. Part of refusing to chase people who won’t chase you back means that you date with intent. You don’t let relationships “just happen”; you make a concerted effort to find and build the relationship you want, with someone who wants to build it with you instead of someone who graciously “allows” you to be around.

And in fairness: sometimes you’ll run across folks who don’t realize they’re doing this, or folks who aren’t necessarily malicious so much as ignorant or misinformed. It doesn’t matter; refusing to play along disincentivizes these games and the folks who promote them. If they actually want a relationship, they can quit playing stupid games and actually ask for what they want.

Making dating better isn’t easy. It requires inner strength, a willingness to face rejection and a willingness to ask for what you need. These can all be terrifying. But they’re also what lead to clearer, more rewarding and more fulfilling relationships.

Nobody said it would be easy. Just that it would be worth it.