How to Overcome Awkwardness
Aristocratic advice on finding your confidence....
It is an unfortunate truth that even the wisest and most well-intentioned of men can be undone by social stumbles.
No matter how much we may wish to be judged on our words and convictions alone, an astounding amount rides on matters as simple as how we enter a room, how we deal with a pause in conversation, and how we physically stand when either speaking or listening.
One man who understood this well was one of the most colourful personalities of Georgian Britain. Philip Stanhope, the 4th Earl of Chesterfield, was indeed a talented speaker and distinguished statesman. But one problem threatened to undermine his legacy — his son.
As the result of an affair with a French governess the boy was illegitimate, and his father knew he would face an uphill battle to enter aristocratic society. So to try and give him a better chance at life, over many years Lord Stanhope wrote a series of letters to guide him, which in 1774 were published posthumously as Lord Chesterfield’s Advice to His Son on Men and Manners.
Unusually, the Earl’s advice begins with the subject of social embarrassment, and a focus on three specific “odd tricks, ill habits, and awkwardnesses”.
Today therefore we take an in-depth look at how Lord Stanhope can help you identify the cause of your awkwardness, and overcome it…
The Three Forms of Awkwardness
Lord Stanhope immediately clarifies to his son why he considers this subject to be such a priority:
“No man is, in any degree, fit for either business or conversation, who does not command his attention to the present object, be it what it will. When I see a man absent in mind, I choose to be absent in body; for it is almost impossible for me to stay in the room, as I cannot stand inattention and awkwardness”
The 4th Earl of Chesterfield, Advice to His Son on Men and Manners
The clear implication therefore is that awkwardness is either a consequence of, or gives the impression of, a lack of attention. The injustice of this of course is that our bearing may well be betraying us. Perhaps we are engaged in a conversation, but if it looks like we are not, then it ultimately does not matter. The effect is either repelling or unsettling, and other parties in the conversation are going to start feeling uncomfortable.
As a result, Lord Stanhope urges us to recognise three behaviours which indicate inattention and foster awkwardness:
1 - Awkwardness of Manner
First impressions of course are crucial. But the first impression has already been made before you speak. It was not based on your words, but on your manner, or Gait.
Lord Stanhope gives an extensive list of common physical stumbles that are off-putting to observers, and difficult to recover from. These range from the most obvious and ‘cartoonish’…
“When an awkward fellow first comes into a room, it is highly probable, that his sword gets between his legs, and throws him down, or makes him stumble, at least; when he has recovered this accident, he goes and places himself in the very place of the whole room where he should not…”
The 4th Earl of Chesterfield, Advice to His Son on Men and Manners
…to the more subtle:
“His hands are troublesome to him when he has not something in them, and he does not know where to put them; but they are in perpetual motion between his bosom and his breeches…”
The 4th Earl of Chesterfield, Advice to His Son on Men and Manners
Into this category falls any physical habit or tic that the passage of years has normalised to us, our family and longstanding friends, but which will be noticed by anybody new and likely distract them. How we cough or blow our nose, for example, or how we respond to accidentally spilling something on our clothes.
For the Earl of Chesterfield however, this is “not in any degree criminal; but it is highly disagreeable and ridiculous in company, and ought most carefully to be avoided by whoever desires to please”. Paradoxically, the most ‘obvious’ awkwardness is usually the one that is easiest to forgive, though that does not mean we should neglect it.
Indeed Lord Stanhope hints at the solution in his discussion of the second form of awkwardness….
2 - Awkwardness of Expression
The Awkwardness of Expression, as Stanhope calls it, is more nuanced. It is a stumble that may well go entirely unnoticed by many observers. But for those who do see it, it tends to be a particular pet peeve:
“THERE is, likewise, an awkwardness of expression and words most carefully to be avoided; such as false English, bad pronunciation, old sayings, and common proverbs; which are so many proofs of having kept bad and low company. For example: If, instead of saying, that tastes are different, and that every man has his own peculiar one,” you should let off a proverb, and say, that what is one man’s meat is another man’s poison;” … every body would be persuaded that you had never kept company with any body above footmen and housemaids”
The 4th Earl of Chesterfield, Advice to His Son on Men and Manners
The use of bad language is obviously repelling. But as Stanhope points out, ‘bad language’ encompasses more than just swearing. It is ‘poor language’, with lazy grammar, limited vocabulary, bungled pronunciation and the treatment of clichéd phrases as though they were pearls of original wisdom.
The truth is that everybody likes words and can appreciate when they are used well. Every cliché exists because the first time it was uttered, all those who heard it marvelled at how this novel combination of words had captured a complex sentiment so beautifully. Repetition however has divorced the words from the creativity which birthed it. An excessive reliance on cliché therefore indicates much time invested in reading, but little in reflection. It has an ‘immersion-breaking’ effect not dissimilar to hearing poorly written dialogue in a film, or realising that a text was written by AI.
However, note that Stanhope uses the word ‘company’ here twice. We will be returning to that shortly…
3 - Awkwardness of the Mind
Awkwardness of the Mind is often the most immediately repelling, for the simple reason that it gives the strongest impression of either intentional or accidental disrespect:
“THERE is likewise an awkwardness of the mind, that ought to be, and with care may be, avoided: as for instance; to mistake or forget names; to speak of Mr. What-d’ye-call him, or Mrs. Thingum, or How-d’ye-call her, is excessively awkward and ordinary. To call people by improper titles and appellations is so too; as, my Lord, for Sir; and Sir, for my Lord. To begin a story or a narration when you are not perfect in it, and cannot go through with it, but are forced, possibly, to say, in the middle of it, I have forgot the rest,” is very unpleasant and bungling”
The 4th Earl of Chesterfield, Advice to His Son on Men and Manners
Let us take heart for a moment that even in the 18th century our ancestors were fumbling around and referring to people as “What’s-His-Name”. But three hundred years have changed nothing as regards the social dynamics. If we are introducing somebody to the conversation only to then scramble trying to remember the name, intrigue rapidly degrades to awkwardness, and the listener is going to be frustrated.
Worse is forgetting to call someone who is actually in front of you by the respectful address to which they are entitled. A ‘Sir’ or ‘Madam’ goes a long way even and especially in 2026. So too does telling an anecdote coherently, rather than interrupting the flow of it with uncontrollable laughter or by realising partway through that you have forgotten key details essential for a third party to follow it.
Now that we have identified the three forms of awkwardness, Lord Stanhope directs us to that word ‘company’ again:
“Now, awkwardness can proceed but from two causes; either from not having kept good company, or ſrom not having attended to it”
The 4th Earl of Chesterfield, Advice to His Son on Men and Manners
Simply knowing what habits to avoid and trying to dodge them in the moment, after all, is a remedy and not a solution. So how can you prevent yourself from even being vulnerable to social stumbles in the first place, and how is the company you keep the key to it?
Here, the Earl of Chesterfield lets us in on an aristocratic secret. He reveals an incredibly common mistake that people make, but which always makes things worse. He also reveals a simple strategy to ensure you are never awkward, or afraid of being awkward, ever again…
