To deal with fear of being judged while dating, stop trying to guess a woman's verdict on you and give both of you a real chance to decide whether you enjoy one another. Wear something that feels like you, speak honestly about your interests, ask questions you're genuinely curious about, and treat differences of taste as information rather than humiliation. If she doesn't fancy you, accept that; if she treats you unkindly, you may choose to leave. A date is a meeting between two people, not an inspection in which only one gets to hold the clipboard.
There is a gentlemen's club in a decidedly fictional corner of London where every member's portrait hangs above an enormous fireplace. Our man Percy is convinced he would be judged less harshly by the painted ancestors than by the beautiful woman he's meeting for a drink.
Before leaving home, he changes his shirt four times. He rehearses his job description until it sounds vaguely like he owns a shipping empire. He nearly throws away his favourite purple pocket square because he worries it might be “too much”.
Percy is doing an extraordinary amount of work to make sure the woman will meet somebody other than Percy.
That's the trouble with worrying what a date might think. You can end up disguising the very personality that might have made the meeting worthwhile.
She is deciding what she likes, not awarding your worth
An attractive woman is allowed to notice your appearance, hear your opinions and decide whether she wants another date. You are allowed to do precisely the same.
Neither assessment is a ruling on the total value of the person being met.
Perhaps she likes sporty men and you love a Sunday wandering through antique shops. Perhaps she admires your humour but wants to live overseas while you plan to stay near family. These things matter when you're considering a partnership.
They don't make somebody superior or inferior. They tell you whether a particular connection might work.
If Percy spends the whole evening trying to establish that she approves of his suit, salary, manners and knowledge of French wine, he may never discover whether he enjoys her company.
A useful change of attention: instead of “Does she think I'm impressive?” ask “Do I like talking to her, and does she seem interested in talking to me?”
That question leads to observable behaviour. The first may lead to twenty minutes of speculation about a raised eyebrow.
The judgement you've imagined may never be made
She looks at your shoes. You decide they're too cheap.
She asks where you work. You decide she's measuring your income.
She says she loves travelling. You decide she's noticed you haven't left Britain for two years.
Notice the enormous leap between what happened and the meaning you've assigned to it.
A woman may look at shoes because she admires them, because she's noticed a loose lace or because shoes are simply located beneath trousers. A question about work is often a question about what occupies your week.
Answer what she actually asks.
“I restore old furniture, mostly tables and cabinets. I love rescuing pieces that look as though they've been thrown through a window.”
That tells her something real. The invented response—“I lead a dynamic international restoration operation”—will be rather difficult to maintain when she asks how many employees you have.
If she genuinely makes a snobbish remark about your occupation, that's new information about her manners. You can respond to it then. Don't conduct the entire conversation with somebody's imagined future insult.
Dress for the meeting, not for an imaginary critic
Making an effort is delightful. Monty is unlikely to argue with a well-cut jacket.
But consider what you'd choose if your date were being held somewhere you already enjoyed, with somebody you hoped to like rather than somebody you feared might dislike you.
Clean, comfortable clothes appropriate to the venue are enough to begin. Add personality where you want it.
If Percy enjoys the purple pocket square, he should wear it. A woman who finds it ridiculous may say nothing, tease him kindly or simply prefer another style. A woman who likes the touch of colour may smile. Percy cannot know in advance.
What he can know is whether he feels like himself while wearing it.
The same goes for hair, height, a modest car or an ordinary flat. Present yourself tidily and truthfully. There is no way to make a first date immune to individual preferences.
Nor should you claim to adore a lifestyle you dislike just to avoid being judged. Being accepted for a borrowed identity would be an exhausting sort of victory.
How to answer a question that makes you feel exposed
“Have you ever been married?”
“Why did you change careers?”
“Do you own your home?”
These may be ordinary attempts to understand another person. They can also feel sensitive depending on your circumstances.
You aren't obliged to provide your full financial history to a stranger before the olives arrive. You can give an honest answer at a sensible level of detail.
“I rent at the moment. I'm happy where I am, and I'm saving towards my next move.”
“I changed jobs because I wanted work I actually enjoy.”
“I haven't been married. I've had relationships, but never quite found the right long-term fit.”
Use the truth of your own life, not these exact lines if they don't apply.
And if a question feels intrusive for a first encounter, there's no disgrace in setting that boundary with good humour: “That's probably a story for when we know each other a little better.”
A date should allow curiosity without demanding every private fact immediately.
Give her the chance to disagree with you
Percy believes a proper holiday involves old buildings, excellent food and absolutely no organised team games. The woman opposite him adores activity holidays involving helmets.
If Percy is desperate to seem agreeable, he'll announce that he too dreams of throwing himself down a mountain on a bicycle.
Within six weeks he may be spending a romantic weekend halfway down a Welsh hillside, regretting a lie that began over a harmless drink.
Better to smile and say, “I'm afraid my ideal adventure ends with a good lunch rather than a broken collarbone. What do you enjoy about it?”
Now she can tell him. He might even discover something that appeals to him, without pretending they're the same person.
Disagreement is not a failure of attraction. It is part of finding out how two people fit together.
You can be playful about camping versus hotels, opera versus rock music or spicy food. Matters of values may need a more thoughtful conversation. Neither requires a performance of total agreement.
A person who must win every discussion isn't excellent company either. The pleasure is in the exchange.
What if you embarrass yourself?
Percy orders a drink, gets the name wrong and somehow asks for a cocktail that doesn't exist.
The barman looks puzzled. Percy's date laughs—not cruelly, but because it was a funny moment.
He can laugh too. “I appear to have invented a new cocktail. I shall expect royalties.”
Then choose something the bar actually serves.
A small mistake needn't become a confession that you're socially hopeless. Nor should you spend the evening explaining why you never normally make such errors.
If you accidentally insult somebody or interrupt her, make a proper apology and adjust. But a botched drink order doesn't require a written statement.
There's a particular freedom in letting a small embarrassment be small.
And if she enjoys holding minor mistakes over your head, you are allowed to notice that, too. The woman across the table is showing you her personality just as you're showing yours.
If she asks something about your looks
Perhaps she notices you're bald, have a beard or are shorter than the man she previously dated. Most people don't make a lengthy discussion out of such observations, but an occasional rude remark happens.
You don't need to argue that she ought to find you attractive.
If she says something unkind, you can say, “That's a rather unnecessary comment,” and decide whether to continue the evening.
If she says something complimentary, accept it rather than telling her she's mistaken. “I'm glad you like it,” is a perfectly decent response.
The important distinction is between a woman privately having preferences and a woman treating you without consideration.
You cannot manage the former. You needn't tolerate the latter.
Nor should Percy spend the evening boasting about his salary because he's convinced she thinks his car is unimpressive. Nothing kills a potentially charming exchange more thoroughly than a man trying to answer an accusation nobody made.
Forget the invisible spectators
Some men walk into a busy restaurant imagining every table is inspecting their date. Others picture an audience of friends who will demand to know whether the evening went perfectly.
A restaurant is full of people mostly concerned with their own food, conversation and occasionally getting the waiter's attention.
You have no need to give a performance for them.
If you're meeting through an app, your private conversation needn't become an account for the lads' group chat. A woman deserves the privacy to be herself without six strangers passing judgement on her messages.
You can also make decisions without announcing them on social media. A lovely dinner remains lovely even if nobody else knows about it.
Return to what you can actually participate in: her story, your reply, whether you have something in common and whether the evening feels mutual.
The imagined audience can order its own dinner.
Remember that you can say no as well
Suppose a woman is accomplished, attractive and terribly fashionable, but she dismisses everyone in the restaurant as beneath her.
You don't have to decide that winning her approval would prove something wonderful about you.
Ask whether you want another evening in her company.
Likewise, if she wants a kind of relationship you're not seeking, you can say so. “I've enjoyed meeting you, but I'm looking for something different.”
A man frightened of judgement sometimes mistakes a woman's interest for an offer he must accept. He begins planning a future before asking whether he genuinely likes the present.
The ability to decline gracefully matters just as much as the courage to invite.
Romantic confidence includes being selective without arrogance, curious without pretending and considerate without surrendering every preference.
It's a considerably more pleasurable way to date than trying to achieve full marks from a complete stranger.
Percy's pocket square
At the end of the evening the woman asks about Percy's purple pocket square.
He is expecting criticism. Instead she says it reminds her of the absurdly dressed magician at her cousin's wedding. Percy laughs and tells her that his grandfather wore purple to practically everything.
She tells him a story about the magician getting trapped inside an inflatable swan. They end up laughing so hard that the waiter glances over.
Perhaps they'll fancy each other enough for another date. Perhaps not.
But Percy has finally learned something about her, and she has met a man who actually owns a ridiculous purple pocket square and likes it.
If you fear being judged, bring your ordinary, interesting self and pay attention to the individual woman rather than the verdict you've imagined.
And if the painted ancestors in the gentlemen's club object, they may take it up with my tailor.