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DATING CONFIDENCETHE ART OF MONTY ✳ EST. 2026
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Putting a woman on a pedestal means imagining she's perfect before you know her and treating her approval as more important than your own judgement. Bring things back to earth by staying curious, keeping your own interests and remembering that attraction should involve two people choosing each other.

There's a marvellous scene I like to imagine in a very grand hotel. A gentleman called Oliver spots an attractive woman across the lounge. She's elegant, laughing with her friends, wearing a green dress that ought to have its own fan club. Oliver takes one look and decides she must be perfect.

Within four minutes, without a word exchanged, he has credited her with exceptional intelligence, exquisite taste in literature, a flawless character and the sort of moral judgement usually reserved for ancient philosophers. By minute five, he has decided he is not nearly good enough to ask whether the seat beside her is taken.

She might, for all Oliver knows, leave wet towels on the bed, talk through films and have a criminally poor opinion of marmalade. He will never find out. He has erected a marble statue where a living woman ought to be, and now he's frightened to speak to the statue.

Putting women on a pedestal means turning attraction into idealisation: imagining she's above you, assuming her approval determines your worth, and overlooking the ordinary business of discovering whether you actually like one another. The cure isn't to become cold, cocky or contemptuous. It's to get wonderfully curious about the real woman while staying in possession of your own life.

I adore women. I wouldn't have spent so much of my imaginary memoir discussing them otherwise. But admiration becomes a nuisance when it requires you to kneel.

01 / FROM THE MONTY FILES

Admire the dress. Don't invent the entire personality.

Illustrated scene featuring Monty for the article: How to Stop Putting Women on a Pedestal (Before You Need a Ladder to Speak to One)
THE ART OF MONTYFILE 048 / AN ILLUSTRATED SCENE

A beautiful woman can genuinely be beautiful. A clever woman can genuinely be clever. You needn't pretend otherwise to remain calm. The difficulty begins when one attractive feature causes you to award her fifty others you haven't observed.

Take the woman in the green dress. She has a lovely smile. That's something you can see. You have no idea whether she is generous with friends, impatient with waiters, considerate in an argument or utterly devoted to a dreadful television programme. You know she's caught your eye. That's quite enough information for now.

Try a little mental correction when your imagination takes flight: “She's attractive to me. I don't know her yet.” No grand psychological ritual; just two honest sentences. You may discover she's extraordinary. You may discover that despite the dress, neither of you has much to say about anything after the starters arrive.

Either outcome is valuable, because you've met a person rather than worshipped a photograph.

02 / FROM THE MONTY FILES

The approval trap, featuring a man who loses his own opinions

Oliver finally goes on a date. She says she can't stand jazz. Oliver loves jazz, owns a shelf of records and once travelled halfway across the country for a live performance. Yet he hears her opinion and replies, “Oh, absolutely. Can't bear the stuff.”

A little later she says she prefers seaside holidays to cities. He's spent years happily exploring old towns, but apparently he's now a devotee of beaches. She prefers dogs to cats. He remembers the cat currently asleep on his sofa and decides not to bring up the subject.

By pudding, Oliver has become a remarkably agreeable gentleman with no identifiable tastes of his own. If she likes him, she's liking a character he's hurriedly constructed in her honour. If she doesn't, he's sacrificed an evening of honesty for precisely nothing.

You can disagree without being argumentative. “Ah, then we'll need separate soundtracks for long drives. I love jazz,” delivered with a grin, gives her something real to respond to. Perhaps she laughs and asks what he recommends. Perhaps she digs in. Either way, a proper conversation begins.

A woman worth dating isn't necessarily looking for a man who has identical opinions. And you're not looking for a woman who requires yours to disappear.

03 / FROM THE MONTY FILES

Watch what happens when you imagine rejection

If asking someone out feels like walking towards a firing squad, inspect the story you've attached to a simple invitation. Are you afraid she'll say no? Understandable. Or have you decided her no would prove something terrible about you: that you're unattractive, ridiculous, unsuitable for romance for the next hundred years?

That second story is the pedestal speaking. It has quietly made a stranger the judge of your entire romantic value.

Here's another way to frame the moment. You are offering a possibility: coffee with someone you find interesting. She can accept or decline for a thousand reasons, most of which you won't know. A rejection tells you she doesn't want that particular invitation. It cannot tell you whether another woman will like your humour, your company or the peculiar way you sing while cooking.

No need to claim you don't care. You can be disappointed. Buy yourself a decent pastry, take the scenic route home and continue with your life. A wounded ego doesn't need to become a state occasion.

04 / FROM THE MONTY FILES

The dangerous business of becoming a one-man concierge service

Some men respond to a crush by trying to provide every conceivable service. They drive across town to deliver a forgotten phone charger. They cancel plans with friends. They buy extravagant gifts for somebody they've met twice. They offer help she hasn't requested and start behaving as though constant usefulness will eventually be rewarded with romance.

Generosity is a splendid trait. Trying to purchase affection with favours is exhausting, and it's often uncomfortable for the person receiving them. A kind gesture becomes an unofficial invoice when you're secretly expecting it to earn you a kiss.

Ask yourself: “Would I be happy doing this if she never dated me?” If the answer is yes, lovely. Help because you want to help and it makes sense. If the answer is no, perhaps the grand gesture belongs back in its box.

Especially beware sacrificing things that matter to you. Don't abandon your friends, hobbies or commitments merely because an attractive woman might be free at the last minute. An interesting man has an interesting life. It shouldn't vanish at the first flutter of a pair of eyelashes.

05 / FROM THE MONTY FILES

Curiosity is the enemy of fantasy

Let's give Oliver another chance. He meets the woman in green again, this time at a friend's birthday. Instead of preparing his entire future in his head, he asks what brought her to the party. They talk about travel, music, and the strange phenomenon of people who willingly get up at five to go running.

He discovers she's funny, adventurous, rather blunt about films and planning to move cities for work. He finds her more fascinating than before — but now for reasons he can name. He also discovers that her plans for the next year may not suit a relationship with someone settled locally.

That's not romance failing. That's the information romance requires.

When you feel yourself building a pedestal, replace the question “How do I make her like me?” with “What is she actually like, and would we enjoy spending time together?” Listen to what she says. Notice how you feel around her. Share your own views and watch what happens. Let the real person gradually take the place of the fantasy.

The result may be attraction, friendship, incompatibility or nothing much. All perfectly normal outcomes from meeting another human being.

06 / FROM THE MONTY FILES

Stop comparing your ordinary Tuesday to her finest photograph

Modern dating gives idealisation a remarkable amount of fuel. A woman's profile may show her on holiday, impeccably dressed, holding a magnificent cocktail beside the sort of pool where even the water appears wealthy. You, meanwhile, are looking at it in old jogging trousers while trying to persuade the washing machine to finish its cycle.

You think she's living a life above yours. But you're comparing an edited selection of memorable moments with your least glamorous hour of the week. She also has laundry, deadlines, bad hair days and the occasional uninspiring sandwich. Nobody's entire existence is conducted in flattering sunset light.

Treat photographs as a glimpse, not a definitive character reference. Read what she has written. Look for a shared curiosity or sense of humour. Then decide whether you'd enjoy saying hello. She is not auditioning to become an ornament on your arm, and you're not trying to borrow the status of a more glamorous life.

A fine romance is two lives becoming more interesting together. It isn't one person kneeling outside the gates of the other's social media account.

07 / FROM THE MONTY FILES

A small exercise I'd prescribe to my more besotted friends

Take a sheet of paper — actual paper, if you can locate some beneath the charging cables — and draw two columns. On one side write “What I genuinely know”. On the other, “What I've imagined”.

“She's funny when talking about her dog” belongs in the first column if you've heard her. “She'll be the perfect girlfriend” belongs firmly in the second. “She invited me for coffee” is knowledge. “Therefore she's planning a future with me” is fiction, possibly with a full orchestral soundtrack.

Then write down three things you enjoy that have nothing to do with her. A football match, a favourite friend, Saturday mornings at the market, a silly hobby that gives you great pleasure. Make plans to keep doing them. Your identity needs ordinary maintenance, just like an old sports car, although ideally with fewer expensive noises.

Finally, choose one reasonable action that replaces guessing with reality. Have a conversation. Suggest a date if the context is appropriate. Ask a genuine question. The action needn't be theatrical. It just has to move you out of the fantasy and into the world where two people can actually meet.

08 / FROM THE MONTY FILES

Confidence isn't deciding she will say yes

A lot of strange advice suggests that the cure for idealising women is to consider yourself superior. Strut. Withhold compliments. Treat everyone as replaceable. I find that notion about as appealing as dining with a man who keeps checking his reflection in the soup spoon.

The better version of confidence is being able to like a woman without surrendering your judgement. You can be impressed by her, fancy her enormously, and still notice when her behaviour doesn't suit you. You can compliment her honestly without begging for reassurance. You can ask her out without pretending that a yes would change your rank in society.

And you can let her discover you. I can't emphasise that pleasure enough. She might enjoy your terrible jokes, your cooking, the fact that you're gentle with animals or that you know the lyrics to a song everyone else has forgotten. You don't need to reveal these things like exhibits at a museum. Simply live them while you're together.

The invitation runs both ways. She gets to decide whether she likes you. You get to decide whether you like her. Neither person is giving the other a medal.

09 / FROM THE MONTY FILES

Take her down from the pedestal and meet her at eye level

Back in our imaginary hotel, Oliver finally approaches the woman in green. He doesn't know whether she'll fancy him. He knows only that she laughed at something he said earlier and that he'd enjoy talking to her.

“Would you mind if I joined you for a moment?” he asks. She might say yes. She might be waiting for someone. There may be a splendid conversation, or an entirely ordinary one that leads nowhere. Oliver can cope with all of it because he's no longer trying to impress a deity.

A woman doesn't become less wonderful when you see her clearly. Often, she becomes much more interesting. She may even discover that you, with your dreadful record collection and questionable marmalade opinions, are interesting too.

So keep your admiration. Keep the butterflies. Keep that slight foolishness that makes romance worth bothering with. Just put away the marble column, the floral offerings and the little plaque engraved “Perfect Woman”.

She's a person, old boy. Say hello to her.

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