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BE YOUROWN MAN

DATING CONFIDENCETHE ART OF MONTY ✳ EST. 2026
THE GENTLEMAN'S READING ROOMARTICLE FILE 076 / 560ALL THE MONTY FILES ↗

To be yourself around someone you like, let her meet your real tastes, humour, opinions and manner of speaking instead of guessing which version of you she'll fancy most. Show genuine interest in her, be honest about small preferences, tell stories you'd normally tell, and allow the occasional awkward moment. You can make an effort with your appearance and manners without inventing a personality. The point is to find out whether she likes you, not whether she applauds the character you've assembled for one evening.

Consider the curious case of a man named Oliver. On Tuesday he tells his mates he wouldn't go near a cold-water swim unless he'd lost a bet. On Friday a woman he adores mentions wild swimming, and Oliver announces that there's nothing he loves more than hurling himself into the North Sea before breakfast.

By Sunday he's shopping for a wetsuit and wondering how the devil his romantic life became a maritime emergency.

Now, wanting to impress someone is hardly a criminal offence. A little polish is part of courtship. The trouble begins when you polish away the very things that make you recognisable.

01 / FROM THE MONTY FILES

The difference between making an effort and playing a character

Monty editorial portrait for: How to Be Yourself Around Someone You Like (Even When You Want to Impress Her)
THE ART OF MONTYFILE 076 / AN ILLUSTRATED SCENE

Getting a haircut before a date? Making an effort. Listening attentively? Splendid. Choosing a better shirt than the one you wore to paint the shed? Highly advisable.

Claiming to adore a band you've never heard, pretending to have travelled to places you cannot pronounce, or mirroring every opinion she offers? That's a casting audition.

You don't have to present yourself with all your flaws displayed like a bargain-bin sale. Manners matter. First impressions matter. But good presentation should be an accurate edition of you, not a fictional autobiography.

Imagine she says she likes a particular musician. A theatrical impostor replies, “They're my absolute favourite,” then prays she won't ask for an album. A man comfortable with himself says, “I've heard the name, but I don't know their stuff. Where should I start?”

The second answer gives her something real to respond to. You may discover a new artist. You may discover you detest the music. Either way, you won't be spending the next six months maintaining an elaborate musical fraud.

02 / FROM THE MONTY FILES

Notice the moment you begin editing yourself

The change is sometimes tiny. You hear yourself laugh a little louder than usual. You agree with a statement before you've thought about it. You mentally reject a perfectly good story because it seems insufficiently impressive.

There's no need to make a grand announcement about authenticity. Simply catch one false note and replace it with something true.

She asks whether you're enjoying a fashionable rooftop bar. You're not. The music is deafening and the menu appears to have been written by a confused botanist. You can say, “The view's wonderful. I'd prefer somewhere we can actually hear one another, though.”

That isn't sulking or insulting her taste. It's offering a piece of information. She may feel the same, or she may adore the place. Either response teaches you something about how you fit together.

Being yourself does not require bluntly delivering every thought that enters your skull. “Your friends are dreadful” is not a charming example of honesty. You can express your own preferences with tact.

The delightful phrase you're looking for is: truth, properly dressed.

03 / FROM THE MONTY FILES

Bring your actual interests into the conversation

Men sometimes conceal hobbies they think are unglamorous. Model trains, gardening, obscure history, birdwatching, cooking Sunday roasts, collecting old maps. Apparently every bachelor is now required to claim his hobbies are skiing, entrepreneurship and looking mysterious on yachts.

What utter rubbish.

The attraction of an interest often lies in the way somebody talks about it. A man who lights up while describing an old motorbike he's restoring can be far more engaging than a man who claims to love luxury travel but can't recall a single meaningful moment from his trips.

You don't need to monopolise the conversation with the carburettor's entire ancestry. Give her the colourful version. “I've been restoring a motorcycle older than some of my colleagues. It currently sounds like a garden shed falling down the stairs.”

Then invite her into the story: “Have you ever taken on a project that got spectacularly out of hand?”

If she enjoys it, wonderful. If she doesn't, the interest remains yours to enjoy. You have not failed because a woman doesn't share your passion for an elderly Italian engine.

Compatibility isn't having identical shelves. It's being able to appreciate what is on one another's.

Here is a peculiar romantic tragedy: two people sit together, each agreeing with the other so enthusiastically that neither learns anything.

She says she hates camping. You had a brilliant time under the stars last summer, but suddenly you're delivering a speech about the barbarism of tents. She says she loves camping. Now you appear to be founding the International Camping Society.

Please select one position and try living in it.

You can say, “I rather like it, actually—but I draw the line at camping without a proper breakfast.” Then find out what she dislikes. Perhaps she had a dreadful rainy weekend in Wales. Perhaps she prefers hotels. There's a conversation to be had.

A playful disagreement can give both people permission to show their personalities. It can also reveal differences that matter. Listen to the substance; don't start an argument for the sport of winning one.

There is a world of difference between confidently holding an opinion and behaving like a man whose entire purpose in life is to correct women over pudding.

If she tells you something important about her values or boundaries, treat that information with care. You're getting to know a human being, not collecting debates for your podcast.

04 / FROM THE MONTY FILES

Flirt in a way that sounds like you

Flirting styles differ. Some people tease gently. Others are direct, or have a dry sense of humour that arrives fashionably late.

If you're the quiet, observant sort, trying to become a booming nightclub personality will exhaust you before the starters arrive.

Suppose you're at an exhibition and she confidently declares a strange sculpture to be magnificent. Your natural style might be a soft smile and, “I was about to say it looked like a coat rack that had won the lottery.” If she laughs and counters, the exchange becomes your shared joke.

A more direct man might simply say, “I've really enjoyed meeting you. You're good company.” There's charm in that too.

Watch whether she welcomes the tone. If the teasing isn't landing, stop. If she's keen and playful, enjoy the momentum. The flirting succeeds when both people want to join the game, not when you've delivered the maximum number of lines.

Most importantly, don't borrow a personality from a stranger's thirty-second video. She can't date your phone's algorithm.

You may find yourself tempted to make fun of yourself before she gets the chance. “I'm terrible at everything,” “Nobody normally likes me,” “You probably think I'm boring.” Delivered once, a little self-deprecation can be funny. Repeated relentlessly, it leaves her with the job of contradicting you.

Nor must you adopt a spotless, invulnerable persona. If you're unfamiliar with a particular restaurant, say so. If you've never been abroad, you can talk about where you'd like to go. If you got a bit lost finding the venue, laugh and admit the truth without giving a twenty-minute account of your incompetence.

An ordinary admission often creates room for warmth. “I wasn't sure which entrance to use; this place has enough doors for a palace.” That's human.

There is no need to disclose every painful experience from your past simply to prove you're authentic. You control the pace at which you share private things. Other people get that privilege as well.

Honesty on a date is not the same as emptying your filing cabinet onto the table.

05 / FROM THE MONTY FILES

When you worry that the real you won't be enough

It can be tempting to decide that a woman with a brilliant career, glamorous friends or expensive tastes couldn't possibly enjoy your ordinary life.

But you don't know that. She might adore the way you speak about your family, your wry humour or your enthusiasm for a Saturday morning market. Or she may want a different sort of partner. You cannot solve that uncertainty by becoming an imitation of somebody wealthier.

Try describing your life with interest rather than apology. “I work long hours during the week, so I make the most of my weekends. I love finding little coastal places nobody seems to know about.” That's considerably more inviting than, “I'm not very exciting, really.”

If you dislike parts of your circumstances, you're allowed ambitions. You can improve your wardrobe, learn to cook or broaden your social life because those things appeal to you. Changing and growing isn't a betrayal of yourself.

Just don't present a renovation that hasn't happened as a finished mansion.

Someone who likes only the imagined version of you creates a miserable long-term arrangement. Every new date becomes another episode of keeping up appearances.

Let's test the principle somewhere more consequential than camping. She says she never wants children. You know you hope to be a father.

Do not swallow your answer because you've become attached to the idea of her liking you. Equally, don't force an enormous life discussion five minutes into a first meeting because you've read that honesty is essential.

When the subject arises naturally, tell the truth. “I respect that. I think I do want children someday, so that's important for me.” Then listen.

Some differences are delightful. One of you loves antique shops; the other thinks they're museums where everything has a price tag. Other differences may mean romance isn't a sensible fit. You learn which is which by allowing both people to be real.

Don't abandon harmless interests merely to please her. But “I'm just being myself” is no defence for behaviour that hurts somebody. Consideration belongs inside authenticity.

Being genuine does not mean being immovable.

Picture a date at a tiny theatre. You make a quiet joke that doesn't quite work. She looks puzzled. You both hear a waiter drop a tray in the corridor, and your brain suggests emigrating.

Instead, smile and say, “That sounded much funnier in my head.” If she smiles, carry on. If not, move to another subject.

That little repair is more revealing than any carefully prepared line. You're showing that a minor stumble doesn't require a completely new personality.

Perhaps she gets something wrong too. Don't pounce. Give her the same room to be imperfect that you'd like for yourself.

A memorable connection often includes a shared mishap: a delayed train, a rain-soaked walk or an attempt to read a menu in a dining room lit like a cave. Such moments become stories precisely because nobody planned them.

A man who can enjoy the unexpected is considerably easier to spend time with than a man silently reviewing his performance after each sentence.

06 / FROM THE MONTY FILES

The question to ask when you get home

Don't ask only, “Did she like me?” Ask, “Did she get to meet me?”

Did you offer your own opinions respectfully? Did you mention something you truly enjoy? Did you ask questions because you cared about her answers? Did you allow her to disagree without trying to rescue the impression you'd made?

And crucially: did you like the woman you actually met, as opposed to the fantasy you'd constructed before dinner?

If the answer to some of those questions is no, you can make a different choice next time. You haven't been sentenced to a lifetime of romantic disguises.

Oliver, our unfortunate new wild-swimming enthusiast, eventually admits that he prefers dry land. The woman laughs and says she likes the sea precisely because he can stay on the beach guarding the sandwiches. Perhaps they become a couple; perhaps not.

At least he won't have to spend their honeymoon pretending to enjoy hypothermia.

Make an effort, certainly. Bring your best manners and a shirt worth wearing. But bring the actual fellow inside the shirt as well. He's the only one who can build a relationship that doesn't require a script.

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