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CONFIDENCEAROUND WOMEN

DATING CONFIDENCETHE ART OF MONTY ✳ EST. 2026
THE GENTLEMAN'S READING ROOMARTICLE FILE 075 / 560ALL THE MONTY FILES ↗

To be more confident around women, stop trying to impress the women you meet and concentrate on having an enjoyable, two-way exchange with one person at a time. Start conversations in situations where a chat is welcome, show genuine curiosity, share a little of your own personality, and express romantic interest when it feels appropriate. You become more at ease by doing these ordinary, rather human things—not by learning a spectacular entrance or pretending rejection cannot sting.

Let me introduce you to a gentleman standing beside the cheeseboard at a friend's birthday party. He is perfectly capable of arguing about football, ordering a complicated cocktail and explaining why the local council has ruined the high street. Then a beautiful woman asks whether the blue cheese is any good, and he replies, “Thursday.”

He has not suddenly lost his personality. He's temporarily placed her on a pedestal so high that normal conversation looks impossible from the ground.

The aim isn't to become a man who can charm an entire room of women in matching evening gowns. The aim is to be the same interesting, courteous fellow who could manage a lively conversation with anybody—and, when he fancies someone, let that interest show.

01 / FROM THE MONTY FILES

Stop treating women as an audience

Monty editorial portrait for: How to Be More Confident Around Women Without Putting on an Act
THE ART OF MONTYFILE 075 / AN ILLUSTRATED SCENE

An audience judges a performance. A woman you're talking to is participating in an encounter. Those are very different jobs.

If you're convinced you must be handsome enough, funny enough, rich enough and smooth enough before saying hello, the conversation becomes a competition with an imaginary man wearing a very expensive watch. Nobody else has met him. You invented him, then lost to him.

Try a different opening thought: I wonder whether we'll enjoy talking.

It turns your attention towards something you can actually discover. Perhaps she's brilliant company. Perhaps you have opposing opinions about the merits of camping. Perhaps there's no connection whatsoever. All perfectly useful information.

Notice the change when you stop delivering a sales pitch. You can disagree mildly, laugh at something unexpected and admit that your knowledge of opera begins and ends with somebody wearing horns. You can ask a question because you'd genuinely like the answer, not because a website called it a “high-value conversational technique”.

You're not beneath her because you find her attractive. Nor are you entitled to her attention because you've gathered the courage to approach. You're two adults who may or may not enjoy a few minutes together.

02 / FROM THE MONTY FILES

Choose the right setting before you choose your words

Confidence isn't the licence to interrupt a woman's day wherever you fancy. Timing is part of charm.

A mutual friend's party, an event with mingling, a shared hobby night or a dating event gives you a reason to be talking. A woman concentrating on her laptop, hurrying for a train or working behind a counter has something else to do. Leave her to it.

Suppose you're both at a wine-tasting evening. She examines the tasting notes as though the grapes have written their own autobiographies. You might ask, “Do you actually taste the blackberry and cedar, or are we all being terribly polite?”

That's a situational invitation. She can laugh and join in, answer briefly or return to her glass. All three responses give you useful direction without forcing her into a conversation.

At the birthday party, the cheeseboard is fair game. Her appearance doesn't need to be the first subject. A man can notice a gorgeous woman without announcing that observation across the buffet.

Sometimes the confident move is not to make a move at all.

03 / FROM THE MONTY FILES

Give yourself a first sentence you can genuinely say

You do not need an opening line that will one day be engraved on a statue.

“You seem to know half this room. I'm James; how do you know the host?”

“Have you tried the food yet? I'm trying to work out whether that spectacular-looking thing is pudding.”

“I've seen you at these classes a couple of times. How are you finding them?”

These are ordinary sentences. Excellent. Ordinary sentences are much easier for another human being to respond to than an elaborate declaration that she has stolen your heart while standing near a fire exit.

Avoid rehearsing an entire exchange. If she says she's the birthday girl's sister, respond to that. If she says she's just arrived, ask how her evening's going. If she gives a polite half-answer and turns away, wish her a good night.

Confidence is an ability to respond to the moment, not the ability to control it.

And for heaven's sake, don't deploy a compliment like a fishing hook. If you genuinely admire her jacket, say so once and move on. A compliment is pleasant; a relentless inspection is not.

04 / FROM THE MONTY FILES

Find the conversational rhythm instead of filling every silence

Here's a useful rhythm for a man who becomes rather too conscious of his own voice around attractive women: notice, ask, listen, contribute.

You notice she's holding a programme from a comedy show. You ask whether she's seen the performer before. She says she came because a friend insisted. You share the story of the worst comedy night you ever attended—the comedian spent fifteen minutes arguing with a broken microphone. Then you let her tell you about hers.

You're offering enough of yourself to be knowable while leaving room for her to be interesting too.

Do not turn the rhythm into a mechanical formula. If a subject takes off, enjoy it. If she's animated about restoring furniture, you needn't drag her back to your prepared question about holidays.

The especially unappealing extreme is a man who asks nineteen questions and reveals nothing, then wonders why the exchange resembles an insurance application. The opposite—delivering a speech about himself—hardly improves matters.

Your job is to contribute, not dominate. The conversation should feel less like being interviewed by a celebrity's publicist and more like discovering whether you share a sense of humour.

05 / FROM THE MONTY FILES

Let your attraction show without making it her problem

Some men manage perfectly friendly conversations but become so determined not to seem interested that they never allow a spark. Others leap straight into flattery intense enough to alarm the chandeliers.

There is a rather enjoyable middle ground.

Make eye contact naturally. Smile when she says something amusing. Offer a compliment about a choice or quality you've genuinely noticed. If you've enjoyed meeting her, say, “I've really enjoyed talking to you.”

That sentence isn't a marriage proposal. It's a warm, honest signal.

If she responds with warmth and keeps the conversation going, you can be a little more playful. “You may be the only person in this room who's defended pineapple on pizza convincingly. I shall have to investigate your other controversial opinions.”

If she doesn't join in, don't escalate the flirtation to manufacture a reaction. Return to ordinary conversation or let it end. Different people enjoy different styles of banter, and there isn't one script that wins everybody over.

Being clear about interest is more attractive than acting permanently mysterious. Being gracious about somebody else's choice is more important still.

06 / FROM THE MONTY FILES

The small choices that make you feel like yourself

Often the discomfort around a woman you fancy comes from surrendering every preference.

She likes a film you've never seen; suddenly it's your favourite. She orders a drink you dislike; you request the same. She asks what you enjoy doing; you announce that your hobbies are “whatever you like doing”.

My dear chap, she's trying to meet a man, not a remarkably obedient mirror.

If she asks whether you like hiking and you prefer a decent pub garden, admit it with a smile. “I enjoy the scenery. It's the uphill portion I object to.” If you both like live music, tell her what you've actually been listening to. You can be curious about something unfamiliar without pretending expertise.

Try stating one genuine preference in each new social encounter. Not as an exercise with a clipboard, but because sharing tastes helps somebody get to know you.

“I'd rather sit where we can hear each other.”

“I love an old-fashioned cinema.”

“I'm more of a seaside-weekend man than a mountain-climber.”

The point isn't to make yourself disagreeable. It's to arrive as somebody with a life, not as a man willing to exchange his entire identity for an attractive smile.

07 / FROM THE MONTY FILES

What confidence looks like when she isn't interested

Here lies the part the glossy dating advertisements seldom photograph: the pleasant conversation that doesn't become a romance.

You ask whether she'd like to get a coffee another day. She smiles and says she's not interested. You say, “No worries. Lovely meeting you,” and move along.

You don't bargain, demand an explanation or invent a devastating farewell that will haunt her for years. You certainly don't search for her accounts later to continue the discussion.

Rejection can feel disappointing. That doesn't mean the approach was a personal catastrophe. You expressed an invitation and discovered her answer. That's all.

And sometimes she will be undecided. Rather than requiring an immediate assessment of your merits, leave her a simple choice. If she wants to get in touch, she'll have the opportunity.

The fellow who accepts a no with good humour is displaying something far more substantial than the fellow who boasts that he never hears one.

08 / FROM THE MONTY FILES

Give your confidence somewhere real to grow

You'll make more headway by enjoying repeated, natural opportunities to meet women than by announcing a grand mission to speak to forty strangers by Friday.

Choose activities you'd enjoy even if you met nobody romantically. Go to a friend's gathering, join a mixed-interest event, attend a regular class or accept an invitation where people naturally chat. Become familiar with speaking to individuals without every exchange carrying the weight of a potential love affair.

That doesn't mean turning the women you meet into training opportunities. People aren't equipment in a gymnasium of male improvement. It means building a social life in which conversation isn't an extraordinary event.

One evening you may enjoy five ordinary conversations and no flirtation. Another time you may meet somebody who wants to keep talking long after the others have gone home. Neither evening is wasted.

If a chat feels awkward, ask a precise question afterwards: did I interrupt? Did I listen? Did I show enough of myself? Those are things you can adjust. “I am fundamentally hopeless around women” tells you nothing useful.

09 / FROM THE MONTY FILES

Know when to ask her out

If you've had a good exchange, she appears comfortable, and you're both contributing, there's no need for a six-week campaign of ambiguous hints.

“I've enjoyed this. Would you fancy a coffee together next weekend—just the two of us?”

Clear, specific, and easy to decline. If she's interested, find a mutually convenient time. If she isn't, accept it without turning the room into a courtroom.

Don't confuse confidence with insistence. Asking once can be charming. Repeating the invitation until she surrenders is not.

There is also no obligation to ask a woman you enjoy speaking to on a date. A woman can be excellent company without being romantically right for you. You are allowed to discover that, too.

10 / FROM THE MONTY FILES

What changes when you stop trying to become somebody else

Return to our man beside the cheeseboard. A different evening, a different woman asks about the blue cheese.

This time he says, “It's quite magnificent, but it does taste as though it's trying to win an argument.” She laughs. They talk about food, then travel, then a little restaurant she loves. He tells her about a disastrous attempt to cook a soufflé. She contributes an even worse kitchen story.

Maybe they'll arrange dinner. Maybe they won't. He doesn't yet know.

But he does know he spent ten enjoyable minutes speaking to a woman rather than ten agonising minutes imagining how he appeared.

That is the kind of confidence worth having: enough ease to offer your real personality, enough curiosity to discover hers, and enough nerve to show interest without demanding a particular ending.

Now, about that cheese. I would still recommend avoiding it before a kiss.

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