It may occasionally come to pass in your romantic life, that you’d like to get in the pants of an entrancing person who appears to be too shy to undo zippers of any sort. To put it less vulgarly, you may like someone, even really like someone, who seems to be too shy to respond to your normal attempts at establishing possible romantic connection.

Such a situation can seem hopeless, or at the least frustrating, even more so if you classify yourself as among the romantically shy. What to do? How to seduce, charm, and woo the shy one you’ve set your sights on, with some hope of success and future satisfaction and yes – the thing you’re really after – true love.
The answer is – it’s not hard, but it is tricky. Therefore, it’s important that you do it right if you want to keep your hopes alive.
As is our wont here at getprettyfedup.com, we’ll attack the problem logically, which means exploring the theoretical underpinnings of shyness, breaking them down into analytical little bits, discoursing at length, and so on. You may or may not find this the slightest bit helpful in your endeavors.
Then we come to the advice part, which tells you exactly what to do. Similarly, you may or may not find this helpful, but what the hell – it’s worth a shot; you’re not getting anywhere on your own. So let’s dive in.
First step: the components of shyness.
Component of Shyness #1: Fear of Other People.
Component of Shyness #2: A Central Nervous System that Tends to Freak.
Component #1 is not only perfectly natural, it’s universal. Everybody is occasionally frightened of Other People and their potential reactions. Everybody is occasionally shy in certain situations or intimidated or hesitant, uncertain, and insecure. If you are never ever shy – there’s something drastically wrong with you. Having something drastically wrong with you in this regard may actually be helpful to you in achieving your life goals as you will be willing to take risks with Other People that others would find daunting. On the other hand, it will almost certainly win you some enemies along the way. If you can handle that, there is no reason whatsoever, from your point of view, to develop a socially appropriate level of shyness. Other People will sincerely and at times desperately wish you would but you don’t care – so fuck ’em.
The object of your desire, however, has socially appropriate shyness in spades however – too much from your point of view – and so we need to look at what generally causes this.
The most common fear that leads to shyness is the fear of getting our delicate feelings hurt. Being rejected, mocked, humiliated, embarrassed, excluded, and otherwise being given the message that whatever intimidating cohort of Other People we are shy around does not like us. As human beings, we tend to dislike that feeling. Our very survival as helplessly social creatures absolutely requires that a certain sufficient contingent of Other People like us well enough to forego doing us any active harm. So that they don’t abuse us, take advantage of us, toss us out of society, steal our money, and reject our loan applications. Basic stuff like that. We need support and assistance to get through our daily lives and if people are busy stamping REJECT on our foreheads or our paperwork, it tends to make things difficult. Most of us experience more of the REJECT phenomenon than we’d really care to, and this leads us to develop healthy (or unhealthy) levels of shyness and fear when dealing with the bewildering mass of Other People that permeates our lives. Basic stuff. Human Being 101. No-brainer.
Logically Enough Then, When Dealing with Your Shy Person – you are going to need to send the I LIKE YOU message as opposed to the I DON’T LIKE YOU message. Hopefully you could figure that one out on your own. But maybe you didn’t think of it quite so straightforwardly or consider in depth how to fulfill this important task in wooing your shy person.
So stop right now, take a moment, and think of it very straightforwardly – I need to send the I LIKE YOU message to this attractive specimen of humanity.
Consider this basic underpinning of your strategy in depth. Ponder for a moment on how to send the I LIKE YOU message. A simple and fairly obvious way to begin your campaign in this regard is the use of sentences that contain the magic ‘I like’ phrase. I like your dress. I like your hair. I like your ideas on that. I like how you handled that. I like your poetry, your website, your blog, your approach, your attitude, your taste in music, whatever the hell you can think of that reasonably approximates the truth. Presumably if you like this person there is something that you like about them. Say it aloud.
Special Tip for the Tact Impaired: It is frequently not advisable when deploying the initial ‘I like’ strategy with a shy person to start out with things along the lines of I LIKE YOUR BOOBS. Or even I JUST REALLY REALLY LIKE YOU A LOT. There are some people you can get away with this kind of direct approach on. Shy people are not usually those people. You want to like something that is uh, detachable, from the person themselves, and boobs, however inconveniently, are not usually detachable from the person who has them. Hairstyle, dress, etc., these things come and go, boobs preferably don’t. The importance of beginning your campaign with a shy person more subtly partly has to do with the Central Nervous System problem we talked about earlier. And it partly has to do with the nature of shyness itself.
So let’s get back to the nature of shyness itself. The principal danger the shy person confronts in dealing with people such as yourself is, as we noted earlier, the danger of getting delicate feelings hurt. The person you like has them. So do you. Even if neither of you is all that fond of your delicate feelings, and even if one or both of you has embarked upon an active campaign to destroy them, you still have them. Everybody does. Delicate feelings are part of the operating system of the normal human being. The Delicate Feelings Feature comes pre-bundled with the infant at birth and starts operating immediately even during the squalling, squirming and screaming stage of early life, and keeps on going til you die. Whether you like it or not, and sometimes you won’t, because delicate feelings do get hurt.
The reason is this. In order to live, we all need certain expectations of the future. Our brains cannot operate without them. There is no point in them doing anything unless there is some sort of a fucking future in which what they do now will make some sort of a difference to how things work out then. People who become acutely depressed often realize this with excruciating clarity. They experience the agonizing sensation that nothing they do will make any difference in their future and this sensation is so dangerously painful and unpleasant to the human brain that it starts saying hopeless and despairing things like ‘What’s the fucking point, anyway?’ And eventually, ‘I might as well just kill myself right now.’ And so on. This kind of shit is dangerous to the human brain and even little tiny newborns come pre-loaded with an expectation of future affection. If they don’t get it – the disappointed infant will on occasion just fucking die. Their brain will fold up, pack up its shit and announce gloomily to itself that there’s no fucking point in living anyway, and the stricken infant will just die. For no other discernible medical reason than disappointment of its pre-existing expectations. The future is a big deal to the human brain. We need it.
Feelings are based, in large part, on our expectations of the future. In many regards, that’s what they’re there for. To help guide us toward the most desirable future we can imagine and avoid the most undesirable future we can imagine. For example, being liked feels good, we want to go in that direction in our futures; being disliked feels bad, we want to avoid that in our futures. It’s more complicated than that, of course, how this is all arranged brain-wise, but the basic principle is easy enough to grasp.
Therefore, obviously, in our dealings with the Shy Person of our desire, we want to create expectations of a Desirable Future to safeguard those all-important Delicate Feelings they are carting around. We want, cleverly, to create the impression that not only do we like something about them in the present, but we may very well like things about them in the future. This is one reason why we don’t leap immediately to the boobs or the passionate declaration of Deep Like. We don’t want to shoot our wad at the outset. We want to give the impression that there are possibly more and better things to come. We want to create a desire for those more and better things by administering small, inherently unsatisfying, yet addictive doses of Like until the person we want is hooked. We want this person to come to regard you as the legal equivalent of heroin, and we do this by using the natural chemistry of feeling.
Sudden Ethical Note: Since I am going to tell you how to get a shy person as powerfully addicted to you as they would be to heroin by manipulating natural feelings – I sincerely and deeply hope you are not going to use this ability for nefarious purposes. Be nice! It is not a good thing to go around seducing shy people you don’t really like and don’t intend to be nice to – just because you can. Some people do this. They figure out how easy it is and they run around seducing shy people they have no real respect for, break their hearts, ruin their lives, and fuck things up for everyone else. They do this, usually, because they under the impression that no one would actually like them for real, and so they come to rely on whatever they can get – artificially induced emotions. You do not need to do this. You wouldn’t be reading this if you did need to do this, so don’t do it.
Okay, so now that you have been warned, you naturally want to know how to cash in on this addictive like heroin thing.
The thing that makes those feelings we are interested in inducing in the shy person of our dreams so goddamn delicate is the obvious and yet frequently alarming fact that the future does not exist yet.
We don’t know what it is, the future, or what it will be, in our own particular case. Often we’d like to, and sometimes we don’t, but in either case, we don’t actually know. We can predict, we can even feel certain, but the truth is – we are forced to guess. And our guesses, in the nature of things, will usually tend toward the I Guess Hopefully My Future Will Be Kinda Good, or the I Am Afraid My Future Will Not Be That Great. We will call the first kind of guess a Hope and the second kind of guess a Fear. Again, we are paddling around in the waters of obviousness here, but since it is in the realm of obviousness that most of us get really screwed up, we’re going to do some exploring.
Some of our Hope guesses and our Fear guesses will be correct, and a lot of them will not be. This element of incorrect guessing is what makes everybody’s feelings so damn delicate. They’re built on air. We’re just fucking guessing! We don’t actually know! Everybody knows this, that our feelings are based on air, although we often forget it. Forget it or not, it makes us nervous. Sometimes really really nervous. We are always dancing at the edge of fatally embarrassing wrongness – our most cherished Hopes and our most worrying Fears can all be proven at any moment to be equally groundless – making us look like a complete fool in front of everyone we know. No wonder we’re so delicate – and no wonder we so often hide the Hopes and Fears that are most important to us.
Meanwhile, your shy person has got a lot of nervousness going on. See, the thing about Hopes and Fears is that, wrong as they potentially are, we really really need them. Particularly Hopes, although Fears come in handy sometimes. But Hopes, those wishful longing Guesses, are both essential and very very fragile, built as they inevitably are, on the expectation of an airy future that does not exist yet.
The reason we need Hopes is, as we explained earlier, that our brains need some expectation that the shit they do will be helpful in gearing us toward a better future than we’d have otherwise, the most Desirable Future we can reasonably set our sights on. If a brain looks around and assesses its situation to be one where there is no possible More Desirable Future and nothing it can do will produce one, it gives up. It twists and thrashes around in a monstrous panic and then it self-destructs.
Not a pretty picture, and even if no one ever explains this to you, you know it, or at least your brain knows it, and it safeguards its Hopes with jealous ferocity. DON’T MESS WITH YOUR SHY PERSON’S HOPES! There is no surer ticket to shy person dating disaster than to endanger or injure Hopes. It is precisely because the brain is fiercely guarding Hopes that your potential favorite person ever has become shy. You should already know this on a subliminal level, that shy people are fragile because their Hopes are both critically important and fiercely guarded.

Now you need to know what your secret weapons in the care, feeding, and manipulation of Hopes will be. They are:
Secret Weapon #1: Patience.
Possibly your least favorite secret weapon. You probably already knew you needed Patience and you don’t like it, and your own Hopes are being endangered by the excessive deployment of Patience, but it is part of the deal with shy people – yourself included. So we’ll deal with Patience Issues in a bit.
Secret Weapon #2: Attention.
One of your shy person’s jealously guarded Hopes is for optimum quantities of Attention. Attention is a vital Hope-sustaining nutrient, that is paradoxically toxic when inappropriately applied. So you will need to get used to using it wisely.
Secret Weapon #3: Kindness.
This is the super-duper secret weapon, often overlooked, ignored, or clumsily deployed. This is the heroin-addiction secret weapon and you’ll need to pay close attention to mastering its secrets for maximum effect. Kindness, by the way, is not exactly the same thing as being nice, although to the Kindness and Niceness Starved, Niceness can be a form of Kindness. Confusing? Sure, but in our logical fashion, we’ll parse it out.
So our shy person is hoping to be treated well, to be liked, loved, understood, supported, admired, respected, listened to, encouraged, helped, valued, appreciated, praised, needed, recognized, sympathized with, and all the rest of that stuff that everybody wants really, whether they’re loud about it or not. They are hoping for satisfying human relationships, and even more secretly hoping for romantic bliss with a member of their favorite sex whom they love. You are hoping that you are a member of their favorite sex. This is all pretty universal, even among people who say they aren’t hoping for any of these things.
Meanwhile, your shy person is fearing that they will be treated badly, ignored, mocked, misunderstood, criticized, rejected, disliked, excluded, overlooked, unloved, unsupported, un-cared for, unappreciated, embarrassed, interrupted, dismissed, degraded, looked down upon, considered unimportant, and generally shoved away from the sunshine of human affection by Brutal and Powerful Other People who will steal and destroy the vital nutrient of Hope they are attempting to survive on.
This pretty much describes everybody all the time. The difference with your Shy Person is that the Hopes are More Important because the Fears are More Powerful. Fear has taken the upper hand in the Hope/Fear equation and is running the show. Fear has decided that it is more life-preserving to avoid rejection and embarrassment, than to obtain understanding and appreciation or whatever other good stuff your person is actually desperate for. It thinks this because it’s come to the conclusion that any dose of rejection over a certain limit will prove Fatally Toxic to all Hopes – and while a person can live a long time on the hope of love, even if they aren’t actually getting any, the projected lifespan of a person without Hope is dreadfully short.
So your shy person is in a dilemma. They can’t get what they want – because if they tries to get it and fail (always a possibility with the Unknown Future), they could die. It’s a life-threatening situation from their point of view. This may seem overblown, and in the case of some shy people, it is, but the cold, hard logic underneath applies to everyone. This is the prison of shyness, and everyone’s subject to it, even if not in this dating area, because we all require airy Hopes for survival.
Logically Enough Then, When Dealing with Your Shy Person – you must GUARANTEE that the dreaded Rejection will not happen. This is partly why the enterprise requires patience. It’s all logical enough, even overly logical, and you could probably figure it out on your own, and maybe even have. But you need to actually act on it. You need to guarantee that you are not going to reject your Shy Person or otherwise fatally injure their Hopes. What makes this tricky, the thing that’s bedeviling you is – how can you prove you won’t reject them if they’re too fucking shy to do anything you could reject? You know that if they flirt with you or say they like you or sleep with you, that you won’t reject them. But they won’t fucking do any of these things. So how can you prove you won’t reject them?
It’s a chicken and the egg situation. You are waiting for your person to lay some sort of egg of emotional vulnerability and they don’t want to because they’re afraid you’ll smash it and laugh. Make a mockery of their Hopes. Prove their fragile unreliability. Reveal the Hopes to be horribly mistaken over-optimistic Guesses. And so on.
You can’t wait for your shy person to lay an egg! You can’t wait for them to say or do anything that even vaguely resembles emotional vulnerability or availability.
No, my friend, you are going to have to un-reject your person in advance, repeatedly, and subtly. For example, if you’re going to try to slide into their DMs, or see if you can get somewhere with someone you met on Facebook, or get something besides a hookup with a shy person you met in an app – you’re going to need to get subtle.
It’s not all about I like you, it’s about how likeable you are in general. Your hair, your political opinions, your religious background, your life experiences, your podcast, your passion for animals, etc. In other words, you are laying the groundwork for it being obvious that you will be reject the person by implying that anyone who would is just downright crazy.
The advanced move is to go from the obvious sources of un-rejection to the potentially less obvious ones. Here is where Attention pays off. You ever so casually make a non-obvious guess as to what their potential sources of ‘oh my god this is so embarrassing no one will ever love me’ thoughts are and ever so casually indicate they’re not a problem. Which makes you wonder out loud why anyone would have a problem with someone with bipolar disorder. Or autism. Or cosplay. Or hair loss. Or whatever.
You crank up casual acceptance mode and let it rip.
Of course, do not do this if casually accepting bipolar disorder is going to be a nerve-grinding impossibility for you going forward. You’d be wasting everyone’s time if you go to great and subtle lengths to convince someone that their obesity doesn’t bother you if in fact it does. I mention this because, strangely enough, people who are desperate for human connection will often try to put up with things they can’t put up with just because they want someone, anyone, in their lives. Give yourself a break and don’t do this. If you can’t hack it, don’t try.

The thing about shy people is that they often lack confidence. Again, this is something you can probably figure out. Because shy people often act like they lack confidence. When you are shy, you often feel a lack of confidence. And so on. Confidence, for our purposes, is the thing that brains develop when their Hopes in a given area come true more often than their Fears. Sometimes this happens, and brains automatically start making something like a mathematical and statistical calculation – ‘if 7 out of every 10 people seems to like me pretty well and 2 out of every 10 doesn’t seem all that enthusiastic but not real hateful, then the remaining one of 10 is obviously an aberration and an asshole. Therefore I, the majestic future-predicting brain, predict that approximately 7 out of every 10 people will like me, which means I ought to approach most people as if they like me, and if someone doesn’t, it means they’re an asshole and statistically speaking, another person who likes me ought to come along soon.’ You don’t ask your brain to do this kind of analysis and sometimes you wish it wouldn’t, but it does. In making its predictions, your brain is much like a stock-market watcher and it relies a great deal on current trend. So that if 3 people are mean to you today, it says to itself, ‘jesus what the fuck is up with people today. This is a really bad day.’ And it tries to adjust its expectations for the day. If things go well, on the other hand, it gets all elated and thinks ‘this is my lucky day!’ and so on. It responds to the chemical effects of current events and uses them in its prediction process.
What happens, or happened, to your terminally Shy Person, is that the opposite analysis took place. A critical mass of Important Other People didn’t like them, treated them badly, ignored them, didn’t listen, criticized, thought they were ugly, or whatever mean thing people can come up with to do (and people can come up with a lot of mean things) and their brains made the appropriate adjustment. It started saying to itself ‘these fuckers aren’t worth it. they’ll probably just laugh at my passion for the violin like everyone in high school did. forget ’em. i’m not revealing any Hopes for destruction and I’m paying big attention to Fears of future misery.’ Brains learn by experience, and logically enough, they often learn unpleasant things from bad experiences. Assume, even if there is no other reason to, that your Shy Person has an acquaintance with Bad Experiences. Most people do, so your guess is likely to be correct, and it will make the secret weapon of Kindness easier to deploy later on.
Shy people are often more affected by certain kinds of Bad Experiences than your boisterous outgoing people. This is partly the result of the Shyness Component #2: A central nervous system that freaks out. Some people, including many of your boisterous, outgoing people, have central nervous systems that don’t really notice anything unless it hits them with an atom bomb. People shout at them ‘Shut up, for chrissakes, SHUT UP!!!!‘ and what their central nervous system actually hears is ‘mumble….shut up….mumble….’ Their own internal sounds are so loud that they can barely hear anything anyone else says.
Such people can have their Delicate Feelings massively wounded when the very loud SHUT THE FUCK UP NOW, PLEASE FOR GOD’S SAKE, SHUT UP AND STOP TALKING!!! message finally gets through because it never occurred to them before that anyone was anything but pleased with their non-stop chatter. Indeed, boisterous, outgoing people can often seem extremely solicitous of other’s feelings because they have absolutely no clue what they are unless they ask very loudly ‘Are you okay??? Can I get you something? God I hope you’re not completely devastated!’ And so on.
These people are practically forced to be boisterous and outgoing to get any contact at all because their Central Nervous Systems are basically deaf. Chronically shy people, however, often have Central Nervous Systems with extremely acute hearing and they can hear everyone’s else feelings at a deafening level whether they want to or not. Excessive stimulation by other people swamps their CNS’s and makes them want to bail. So when someone tells a shy person, or a person with this kind of CNS to ‘shut up’, their CNS hears it as a devastating explosion rocking several ports in the South Pacific and undoubtedly causing permanent damage to their shattered CNS eardrums. One little ‘shut up’ at the age of 7, and some central nervous systems are disinclined to say anything again until the age of 70. They don’t like being yelled at. It hurts and their CNS’s just freak.
Therefore, paradoxically, in our dealings with the Shy Person of our desire, we are either going to have to be very quiet and centered or we are going to have to be very loud. Either will work. If you are a certain type of loud person, you can eventually wangle yourself into an ongoing relationship with a shy person by completely ignoring the fact that they have been extremely hesitant the whole time. This method, in fact, is how lots of shy people get into relationships – they never have to lay an egg, reveal any Hopes or Fears, or actually do anything but be swept along by someone Loud, Boisterous, and Confident. This is a perfectly acceptable way of doing things and if this works for you, you don’t need my advice. Deploy your natural Boisterousity.
I am not going to guarantee whether the relationship will work out, but you can usually get one going. You may like your Shy Person very much because they balance out your loudness with their quietness. And they may like you because you do all the work of outgoingness that they can’t. On the other hand, you may come to sincerely hate each other, if you ever actually get to know each other. It’s a gamble, as love so often is.
On the other hand : If boisterousity doesn’t work for you, then you are going to have to deploy Quiet Centered Listening. Some of you are naturally talented quiet centered listeners and some of you are just terrible at it. But either way, Quiet Centered Listening is the means by which you will activate your secret weapons of patience, attention, and kindness and so next we’ll delve into how you actually do that shit, so that if your other attempts are getting you nowhere, at least you’ll know what you’re doing now. That wasn’t a very good sentence but you know what I mean.
If you still have any interest in pursuing your Shy Person and haven’t completely given up under the nervous strain of reading about their quirks and foibles, then we’re heading into the homestretch. This is where we tie all the threads together.
First, I want you to think of your shy person as a housecat. This may be an unfortunate metaphor if you don’t like cats, but it’s the best one I can think of. Cats have a reputation for being rather mysterious, unlike dogs, who seem incapable of mystery, although they can occasionally pull off being very strange.
Anyway, cats are reputed to be independent, capable of fending for themselves, prideful, standoffish, aloof, and so on. Again, unlike dogs, who more closely resemble the boisterous, outgoing people of the world. But the thing about cats is that once a cat gets to know you, or feel comfortable with you, it often devotes itself assiduously to obtaining physical affection from you. It’ll jump on your lap, purr, roll around lasciviously, rub against you, and so on. Even if a cat doesn’t know you, it may very well seek love and attention from you, especially if you are allergic to or don’t like cats.
There is a certain myth that ‘nice guys’ and ‘shy girls’ are the most wild once their reserves have been penetrated. There is some validity to this, although you shouldn’t bet the farm on it. The point is, that like cats, shy people are gluttons for love and attention and affection and frequently phsyical contact of all kinds (including some kinds that are hopefully among your favorites), given any sort of decent opportunity.
There is a reason why a cat will go straight toward the one person in the room that hates them or is allergic to them. It has to do with their central nervous systems – like a shy person’s, a cat’s is easily overwhelmed, and thus they gravitate naturally toward people that aren’t making loud noises, or frantic gestures to get their attention, and so on. People who hate cats are often trying to avoid them altogether, which cats much prefer to someone that chases them around yelling ‘kitty, kitty!’ The cat sees the person who’s trying to avoid them, and thinks to itself, ‘ah, calm centeredness, exactly what I crave, appreciate, and adore – what a wonderful human – I shall reward them by seeking their company for comfort and companionship.’
There’s a lesson here. Shy people are like cats in a remarkable number of ways – and calm centeredness attracts them. What we want to do is make the shy person comfortable, so that they will eventually entertain and fascinate us for the rest of our lives with their mysterious knowledge, playful tricks, hunting ability, and exotic allure. Like cats, shy people have excellent memories, which means they don’t tend to forget anyone or anything that injures them. Be careful!
Time for the Step-by-step Plan
All right, let’s stop screwing around with domestic animals and get down to brass tacks. We’ve already established that 1) we have to convey the message to our favorite Shy Person that we like them without being overly direct about it; 2) that we want to string things along by cleverly planting the expectation of a More Desirable Future with us in our Shy Person’s mind; 3) that we cannot wait for them to make open up first; 4) that we must guarantee them that we will not reject them – in advance of them doing anything that we could actually reject; 5) that sometimes we have to be indirect and general in our ‘I like’ statements and 6) that we are going to use Calm Centered Listening to deploy our secret weapons of Patience, Attention, and Kindness. So we already know a lot. Let’s turn this information into a step by step plan.
Step 1. Attack Uncomfortability.
Being too shy to get into a relationship is not the end of the world, but it is often inherently uncomfortable. We attack uncomfortability with our ‘I like’ statements directed to some aspect of how our Shy Person functions. Remembering that our Shy Person is like a cat with easily overwhelmed Central Nervous System, we strictly limit our ‘I like’ statements. If we don’t, we run the risk of making them more uncomfortable, over-exciting their CNS and making them want to withdraw and get away. So we dose out one ‘I like’ statements slowly, carefully, and judiciously, always checking for attempts to flee physically or mentally. This is why we needed patience.
There’s an upside to this patience though. People who get over-enthusiastic with the ‘I like’ statements and the compliments and the wooing and the whatnot right off the bat – they’re often narcissistic charmers who end up hellish to live with later. Or easy come easy go people. People are naturally, and unconsciously more invested in things that take patience to build. You and your shy person have a better chance of an enduring relationship because you had to craft the damn thing with so much care.
Meanwhile, while judiciously doling out our ‘I Like’ statements, we are making use of the Future Expectations module that creates feelings to subtly create a feeling in your crush that you will dose them with compliments whenever you are around them. Their brain will, in most cases, start expecting that positive feedback, look for it, want it, and be magically drawn to you as the dispenser of reliable ‘I like’ statements.
It’s the opposite of the ‘insult them and they will be attracted to you strategy’ that some others swear by but which is poison to our passionate shy person.
So we are slowly getting your shy person addicted to you. As a source of comfortable likingness. Pretty simple. This works with just about everybody, not just shy people, and this technique’s use is limited only by how willing you are to like various aspects of the Other People. In this case, we hope that you already like the person you’ve spent so much time reading about, so it’s not much of an issue.
Note that these ‘I like’ statements are a form of Attention, the vital nutrient we alluded to earlier. Notice how careful we are not to overdose our person. Remember that too much attention is toxic to shy people. Don’t be deterred if your Shy Person does not compliment you back or make similar ‘I like’ statements. They might, or they might not. It’s irrelevant. You are in control here, at least you are until your person leaps into your lap demanding physical attention, so make use of the control you have now and just don’t fucking worry about any lack of response.
Step 2: Attack Lack of Confidence.
Now that we have established our ability to comfortably deal with basic ‘I likeness’, we move on to establishing interest in love and romance. We make the person confident in their real relationship desirability by, again, making statements about the person that indicate they’d a good relationship partner. Like when they want to talk exclusively about how everything in their life is going backwards these days. We simply smoothly and eloquently say ‘well you seem to handle it really well. Seems like that would be the kind of quality people would really appreciate in a relationship.’ And so on.
Again, we dose this out slowly. This is why we have to be so goddamn patient. After a month of this, your person is going to know that you’re interested in love actually and it’s going to drive them crazy. Good. You are building things to a critical mass, where something is going to have to happen to resolve the tension. That’s what you want. In the meantime, you are establishing that you will not go into reject mode if love were to develop and be articulated. But you are doing it slowly, so their CNS can get used to it. Your person may still have their doubts and questions about you, but something is building.
Step 3: Remember that cats and Shy People are easily embarrassed.
You may not know much about cats but one of their interesting features is that if one takes a risk and fails, as for example, by trying to leap onto the dining room table and missing, the cat will often walk away haughtily, as though trying to give the impression ‘I meant to do that. Turning into a panicked falling mass of outstretched claws and landing ungracefully on my butt is exactly what I was trying to accomplish.’ Shy people are like this. They feel inadequate at the drop of a hat, don’t like this, and try to hide it.
Dogs, like boisterous outgoing humans, are frequently too stupid to realize they should be embarrassed, but unfortunately or not depending on your point of view, Shy People rarely are. Thus, when a Shy Person shows signs of embarrassment, we ignore it. Important point! In Step 2, you will have established multiple opportunities for deeper realms of affection. Some of these will embarrass your Shy Person.
They may make a pathetic, or awkward attempt to respond, or otherwise reveal themselves to be romantically incompetent. Ignore this! It is vital to ignore the Shy Person’s failures and inadequacies, they don’t like them and they don’t want any attention drawn to them. This is why we are careful with attention. We don’t tease the Shy Person or make fun of them, etc. Shy People are too much like haughty cats for this. You can play with a Shy Person, but not make fun of one. If you need a mate you can embarrass, pick someone else. Drop the whole endeavor right now and pick a boisterous, outgoing person you can embarrass with impunity. By ignoring the Shy Person’s embarrassments, and there will be some, quite possibly, in areas beyond the realm of romantic engagement, you are establishing yourself as a non-rejecting person. Shy people are notoriously sensitive, you may or may not be yourself, but don’t get anywhere near this particular mistake with a 10-foot pole. If they act all embarrassed over something and don’t want to talk about it – don’t talk about it! Don’t try to shore up their confidence by pointing out at length that embarrassment is misplaced, just fucking ignore it –act like there is nothing wrong whatsoever, and just move on. This is a common blunder in dealing with Shy People and it’s left many a hopeful out in the cold. Take heed.
Step 4: Lure. 
A shy person’s first line of CNS defense is withdrawal. The antidote to withdrawal is luring. You are going to lure your shy person with attention, kindness, and goodies. Let’s say your shy person got embarrassed, which you cleverly ignored, but now they seem to be trying to pull back or withdraw into their shell.
So now you have to withdraw too. It’s a cat and mouse game, since we are using the cat analogy. You have to find out what they like by drawing them out with patient questions. Shy people are notoriously passionate, just not in front of people they don’t trust. Shy people, and introverts in general, are also notoriously talkative – on the subject of their passions, which they generally assume no one else shares.
Without apparent bouncy enthusiasm, you just ask about it, so they’ll do the talking. At least 8 times out of 10, they will, once you get them going. Now you simply pay attention. Not obsessive attention, just attention.
If you can’t do this – shy people are not for you. Ditch the enterprise at this point. Shy people love love love to delve into their passion, whatever it may be, animals, music, novels, what the hell ever. Notice that we have cleverly gone forward in the romantic arena and pulled back. We have made this game interesting to their brain. We are applying intermittent reinforcement, piquing interest and then pulling back. This is the most addictive form of reinforcement a human being can encounter. So we use it.
Shy people are often easily bored by others! We circumvent that difficulty by luring the shy person into doing much of the talking on occasion. It is a hugely common mistake to try to overcome a shy person’s withdrawal by doing all the talking yourself! Don’t make this mistake. Ask gentle questions. Gentle. Not – so what’s your passion? More like – you have a lot of books on the newspaper business, are you interested in journalism? This is why we use Attention. We look around for things to ask questions about. Then we ask them. ‘That painting on your wall looks really interesting. Do you know a lot about art?’ The answer may be no, but your person knows a lot about something.
I’ll say it again in a different way – to a Shy Person, having someone to share interests with is a form of attention so powerful, it is indeed like morphine or heroin. This is tremendously important to shy people, and since it’s a powerful drug be careful with it. Paying attention to a shy person’s interests is a form of Kindness. Kindness is the Killer App. Be aware of that. You can’t think of shy people as being normal; shy people are more interesting than normal. They are particular. You can’t just dive into – ‘hey wanna make out?’ and hope that turns into love. You’ve got to love by taking the route of their passions. Once you get the passion button turned on in them, the chemicals will start swirling.
Step 5: Attack Fear.

Remember that shy people are afraid – like everyone else is. They’re just more afraid than most. Your kindness is the magic antidote to fear and it’s powerful, so proceed accordingly. What kindness is, in this context, is the application of pain relief. Let’s say our Shy Person is distressed by pandemonium. Uproar, tumult, chaos – they hate ’em. Miscommunications really bother them. Loud people who don’t listen bother them. Having to speak in a crowd bothers them. Trying to concentrate in a noisy room or where lots of people are talking or yelling, these things bother them.
Maybe they don’t, but lots of shy people are bothered by this kind of shit. So what you do – the kind thing to do – is make the pain go away. If miscommunications bother them – then you listen – until they’ve communicated everything they wanted to but screwed up in whatever encounter bothered them. If they’re trying to do something nerdy like read in a crowded cafeteria, offer to take them to some place quiet. If they has to do some work and are bothered by distractions, make those distractions go away. If they wants to know something and are afraid to ask someone the answer – ask it for them. Whatever causes the pain that they’re too fucking shy and embarrassed and haughty and reserved to deal with themselves – step in and make it go away without acknowledging any inadequacy.
This is the essence of kindness. Helping someone without belittling them. The resulting pain relief produces a tremendous numbers of chemicals and if you do this your Shy Person will bond to you in a gushing helpless way even if they doesn’t want to. You may not want to do the things that will make your shy person’s pain go away and so you’ll have to make a choice. If you can do them and you like doing them – you’ll have yourself a possibly life-long deal with your Shy Person, I can almost guarantee it.
The problem is – you may not know exactly what causes your Shy Person’s pain or embarrassment or inability to be bold or even straightforward. This can make you feel helpless. This commonly happens. That is why you pay Attention and you use Calm Centered Listening to figure out what is causing the distress. Again, Kindness is the Killer App when it comes to shy people.
What happens is that the pain relief produces a gush of endorphin-like bonding chemicals (endorphins are the body’s own naturally produced heroin type substances, we were using the heroin analogy on purpose) in the shy person and the bonding will inevitably go towards you if you are the one who came to the rescue. This bonding has a good chance of destroying the shyness barrier.
So let’s go over this again. First – you patiently pay attention until you can see when your Shy Person experiences the pain, embarrassment, distress, fear, etc. that shy people are prone to. If you cannot see outright, you use your questioning and calm centered listening skills you used in the Luring stage to see if you can figure out what this person needs.
Second, you think real hard (if necessary) of something you can do to make alleviate distress and initiate pain relief. If it doesn’t require hard thought – you just do it. Third, and most importantly, you do not acknowledge that there is anything wrong with your Shy Person. You don’t say ‘huh, you’re a real nerd. I guess you need quiet, huh?’. You just offer to take them to a quiet place. You just ask the loud people to pipe down a bit. You just do it, and you never acknowledge that their fear or pain or reaction might be over the top.
4th – you watch for feedback clues. If your person appears flushed and really grateful, look adoringly at them and see if they respond with an equally adoring look. If she does, now’s a good time, give yourself a big thumbs up and allow yourself the fantasy of receiving that adoring look for many years into the future.
However – if your person is showing signs of ‘I could have done that myself, don’t be so pushy, or something similar – hang the fuck back. You will annoy your Shy Person big time with a miscalculation here. So pay attention. Chalk it up to experience and look for an alternate way to deploy kindness.
Once you’ve unleashed your Shy Person’s passion by tapping into their areas of interest- and you need to do this for maximum chemical effect before deploying the Kindness Killer App, you’ve pretty much got things stirred up enough that you can just skip any awkwardness. Remember, you’ve carefully laid the groundwork for this moment, you are both stirred up by the equivalent of your emotional rescue of Shy Person and there is no need to overthink things at this stage. You just want to get to this stage.
Step 6. If an initial deployment of Kindness does not lead to adoration (and it may not), use Reassurance.
You can use Kindness a multitude of times with a cumulative effect, so no worries if it doesn’t produce nirvana during your first foray. With Reassurance, we are merely going to take our initial techniques and bump them up to the next level. What you do is you scout around for some sort of project your person is interested in, and then you support it. If your person seems unwilling to divulge any sort of project, go back to tapping into their passion and use your Calm Centered Listening skills to ferret one out. Shy people very often assign themselves projects that are inherently difficult for them, involving as they do, some sort of overcoming of shyness.
Say your Shy Person wants to ask for a raise or negotiate one. They will likely find this intimidating; most people do. This is a good project for you to deploy Reassurance on. What you do is make Positive Declarations of Support. You offer to let your person role-play or try out her arguments on you. You state that you’re on their side, that you think it’s a good idea, that you have confidence, and so on. The confidence is important, because you are essentially allowing someone else to borrow your confidence to supplement their own low reserves. This is extremely helpful.
This is more or less what good friends do for each other anyway, and this actually sort of pushes you sideways into the friendship zone, but it’s okay, we’re willing to take that risk. Why? Because shy people, or people who are romantically shy, are often of the opinion or experience that their romantic liaisons do not lead to Reassurance and support. You win bonus chemicals if you get your person to reveal insecurities, doubts, hesitations, lack of self-assurance, all those Fears we talked about earlier. At this point, you are at the magic intersection of Hope and Fear where feelings begin and if you can get yourself in here in a positive way, the Shy Person will bond to you with perhaps alarming loyalty.
Everybody wants someone like this in a mate, and if you’re willing to do this, you can write your ticket. There’s a myth that what people want in a mate is good looks, status, money, power, a huge number of followers on social media and other Impressive Shit.
In reality, the vast majority of people on the planet (and there are more than 7 billion), go for kindness and a sense of humor. Go figure!
Bottom line, if you make it all the way to Step 6, you own this person’s heart – or at least as much of it as they’re willing to let anyone have a claim on. Good work! And look at you – you did it all by being a disgustingly good, nice person. You didn’t even have to compromise your principles or change your character or even be that brave. Now it’s time for:
Step 7. Don’t wait.
If you’d been willing to just go for it earlier, it wouldn’t have taken you this long. But you weren’t, for whatever reason, you actually wanted to win this person over, be sure they were ready; you didn’t want to be rejected yourself. Maybe you’re just as shy as they are. Maybe you’re more scared of rejection than any Shy Person you’ve ever met. Don’t worry. By this time, it really doesn’t matter how shy either or both of you are. You’re past that point. You trust each other. You know each other. It’s too late for shyness, really. You’ve already done all the work. All the hard parts are over. Your chemicals have melded. The barriers have essentially fallen.
So you just say it, whatever it is, or you just do it. Thanks to all your shyness attacking techniques, which you’ve been using for maybe 3 months, if you’ve been very methodical, the level of intimacy between the two of you is actually quite high. Your shy person can now tell you things no one else gets to hear. And you can say things you wouldn’t tell other people. This is just a side effect of doing the various things that win trust, the Calm Centered Listening and so on. You’re not making a proposal in the dark. You know something about this particular person because you’ve been paying attention. And you can therefore get an honest answer. The risk of pain is actually quite low.
You’ve just done the opposite of what most people do, that’s all.
Most people establish a relationship first – and then do the labor of building up trust, assurance, confidence, and so on, in whatever areas they are needed. They get to know the person while they are in a relationship with them. You simply did the homework first. You got to know them before either of you decided it was love.
It’s a cautious approach, but there’s nothing wrong with it. It reduces risk, and the fact is, you’re going to have to do some of this shit, regardless, either before or after the fireworks. There’s nothing wrong with doing it first. In fact, it often makes things more smooth and long-lasting once things get going. And this can be greatly to your advantage, because if you are a shy or cautious person, god knows, you don’t really like the strain and the wear and tear of getting yourself into and out of god knows how many romantic relationships before finding one that works. So you’ve saved yourself a lot of stress and found someone you can be reasonably assured of. Good work. Props to you. Most people aren’t like you – but screw ’em. If they like stress and strain, let them take that route.
Finally, if fear rears its ugly head at any point – in either of you – deploy your Calm Centered Listening skills to get through it. These puppies will get you through anything with your shy person. Arguments, misunderstandings, embarrassments, you name it. If something absolutely needs to be said, wait until you’re calm, and then say it. Calm Centered Listening Skills don’t work for all things or all situations – but they do work with your Shy Person and they do work in alleviating fear or insecurity. So fucking deploy them. Use them to your advantage.
All right – by now you have done so much work that I sincerely hope you end up marrying your Shy Person so you never have to go through this again. And I have every confidence that you will – anyone who made it through all seven steps deserves marital bliss and I am here to wish it on you and the Shy Person you worked so hard to get.
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