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THE MONTY FILES / ISSUE 203ARTICLE FILE 203 / 560

HOW TO STOP COMPARING YOURSELF TO OTHER MEN WHEN YOU'RE DATING

DATING CONFIDENCETHE ART OF MONTY ✳ EST. 2026
THE GENTLEMAN'S READING ROOMARTICLE FILE 203 / 560ALL THE MONTY FILES ↗

He's taller, younger, richer, funnier or apparently capable of bench-pressing a Ford Fiesta. Meanwhile, you're supposed to be enjoying a date. Monty would like a word.

If you want to stop comparing yourself to other men, stop using a stranger's best feature as the yardstick for your entire worth. Notice when you're making the comparison, ask what you actually know about the other fellow, and bring your attention back to the woman you're meeting. Dating isn't a contest where every man receives a score and the highest number wins. She has her own preferences, and so do you.

It sounds straightforward, but I know how the comparison game begins.

You're at a friend's birthday party. A rather handsome chap walks in. Tall, well dressed, excellent hair. He makes everybody laugh. You immediately decide that if there's a woman you fancy in the room, you might as well go home.

Never mind that you've barely spoken to him. You've already crowned him Champion of Men and retired from the competition.

Old boy, nobody appointed you judge of the annual Handsomest Bloke in Lancashire competition.

You've invented the event, awarded the trophy and gone outside to sulk beside the bins.

01 / FROM THE MONTY FILES

The Trouble With Comparing One Feature to a Whole Person

Monty enjoying a social occasion, illustration for File 203
THE ART OF MONTYFILE 203 / AN ORIGINAL MONTY SCENE

Suppose a man beside you is six foot four.

You're five foot nine.

If you're insecure about your height, that one difference can become the entire story. You imagine that every woman in the room would prefer him.

But you know nothing about how he behaves on a date, whether he's interested in the same sort of relationship or what the woman you're talking to actually finds appealing.

You have taken one visible fact and invented several invisible ones.

The same thing happens with money, looks, career, clothes, social confidence and fitness.

He's got a better car. He's younger than you. He's funnier in a group. He's got a spectacular jawline that appears to have been manufactured by a specialist engineering firm.

Fine. Those things may matter to some people. They don't tell you who he'll be over dinner, how he'll handle disappointment or whether he's compatible with someone.

The point isn't to pretend physical attraction doesn't exist. It does. The point is to stop treating your insecurities as if they can speak for every woman alive.

02 / FROM THE MONTY FILES

You're Often Comparing Your Ordinary Day With His Highlight Reel

Think about the man you see on social media.

You know his best photographs, favourite holidays and greatest accomplishments. You don't know whether he spent three hours choosing the photograph, argued with the hotel receptionist or went home feeling lonely.

A dating profile works the same way.

Someone has chosen five flattering pictures and a few details designed to make a good impression. That isn't a documentary of his entire life.

Meanwhile, you judge yourself using the moment you couldn't think of anything to say at a party, the haircut that went wrong and the bank balance you checked on an unfortunate Tuesday.

It's an unfair comparison even before you've finished making it.

Research into social media and appearance comparisons has found associations with body dissatisfaction and lower self-esteem in some groups. That doesn't mean every photograph is harmful, or that deleting an app will instantly change how you feel.

It does suggest that constantly measuring yourself against carefully selected images is a rotten way to decide whether you're worth dating.

Put the screen down and consider the actual people you know. Most of them are far more complicated—and far less polished—than their pictures suggest.

03 / FROM THE MONTY FILES

When Another Man Gets More Attention at a Party

Here's a scene that may be painfully familiar.

You're at a barbecue, chatting with a few people. Another bloke arrives and immediately becomes the centre of attention. He's telling a brilliant story and everybody's laughing.

You could enjoy the story, add something to the conversation and carry on having a decent evening.

Instead, you start comparing.

He talks more confidently. He knows more people. He made the woman you fancy laugh. You suddenly feel as though you're failing a test that nobody announced.

That's the moment to challenge the story in your head.

What have you actually observed? A man told a funny story. People laughed.

That's all.

It doesn't mean he's a more attractive partner than you. It doesn't mean the woman who laughed has decided she wants to date him. It certainly doesn't mean your own presence is now unnecessary.

If you have something worth saying, say it. If not, listen. You don't need to win the room.

A quieter chat with someone later may suit you far better than competing for the audience.

04 / FROM THE MONTY FILES

What If He's Genuinely More Attractive Than You?

Perhaps, by conventional standards, he is. There's no need to pretend the two of you are identical.

There will always be men with more money, better hair, stronger arms or more polished social skills.

There are also men who are kinder, more reliable, better listeners and more compatible with a particular woman than those apparently impressive fellows.

But let's not turn that into another fantasy where you secretly possess all the moral virtues and the attractive chap must be an idiot.

You don't know him. He might be lovely.

You can acknowledge that somebody has qualities you admire without making him your enemy or making yourself worthless by comparison.

The useful question is not, “Am I objectively better than that man?”

It's, “Am I someone I respect, and am I getting to know women I might actually suit?”

Those are things you can do something about.

05 / FROM THE MONTY FILES

Three Comparisons That Commonly Spoil Dating

“He's got a much better job than me.”

You're a mechanic. The man across the room is a solicitor.

You decide that women will obviously prefer his salary, suit and important-sounding title.

Some people value financial success highly. Others place more weight on shared values, kindness, humour, stability, ambition, lifestyle or simply enjoying one another's company.

A job title doesn't tell the whole story.

If you're unhappy with your work, you can take steps towards something better for your own sake. But don't invent a rule that nobody will fancy you until you've acquired a business card with an impressive title.

A man who's interested in his work, does what he says and treats people well has plenty to talk about.

“Her ex was better-looking than me.”

She happens to mention that her ex played rugby. You see a photograph of a broad-shouldered fellow and start wondering how you could possibly measure up.

Their relationship ended, and you don't know why. The fact she once dated him doesn't make him the standard every future man has to match.

She's choosing whether to get to know you now. Constantly comparing yourself with a past partner turns a new relationship into a contest with somebody who isn't even in the room.

Don't interrogate her about how you compare. Don't ask whether he was better in bed, earned more or dressed more stylishly.

Let the past stay where it belongs unless there's a genuine reason to discuss it.

“My mate gets dates much more easily.”

Your friend seems to meet somebody new every fortnight. You're delighted if a woman replies to your invitation before the end of the month.

It can sting.

But ask what you're actually comparing. Number of dates? Number of enjoyable dates? Compatibility? Whether anybody wants a lasting relationship?

A man can have twenty first dates and not find what he's looking for. Another can meet one compatible person and build something lovely.

There is no competition to collect the greatest number of romantic appointments.

If your mate is good at starting conversations, you can learn from him. You don't have to copy his entire personality—or resent him for having an easier time.

06 / FROM THE MONTY FILES

A Date Where the Comparison Gets in the Way

You're meeting a woman called Laura for coffee.

She's telling you about a hiking trip she enjoyed with friends. You notice the man behind the counter is tall, charming and chatting easily with everyone.

You decide Laura must find him more attractive.

Now you're distracted. You barely listen when she asks about your weekend. You answer too briefly. She asks a second question and you miss half of it.

Finally she says, “Are you all right? You seem somewhere else.”

You could say, “Sorry, I lost my train of thought. You were telling me about that walk—where was it?”

And return to the actual date.

Or you could spend the next hour trying to out-charm a man who's at work making cappuccinos.

The second option is exhausting and ridiculous.

If Laura agreed to meet you, give the meeting a proper chance. Stop conducting an imaginary competition with everybody who happens to be nearby.

07 / FROM THE MONTY FILES

Be Careful With the “She Could Do Better” Thought

This one looks humble, but it can become a problem.

You meet a woman you really like and start thinking she's out of your league.

She's successful, funny, attractive and interesting. You feel lucky that she's agreed to a date.

It's fine to admire her. The trouble starts when admiration becomes disbelief that she could genuinely want your company.

You may over-apologise, agree with everything she says or avoid expressing your own opinions because you're afraid she'll discover that you're not good enough.

But she isn't conducting a charity programme for unfortunate bachelors.

She's a person choosing whether she enjoys being with another person.

Let her discover who you actually are.

If she doesn't like you, that's disappointing. If she does, you shouldn't have to argue her out of it.

08 / FROM THE MONTY FILES

What You Can Improve Without Turning It Into a Race

Perhaps your comparisons point to something you'd genuinely like to change.

You're unhappy with your fitness. You want to dress better. You'd like to become more comfortable talking in groups.

Those are reasonable ambitions.

But make them personal rather than competitive.

Exercise because you'd like to feel stronger and healthier, not because a particular bloke has bigger shoulders.

Choose clothes that fit properly because you enjoy looking after yourself, not because you think you need to impersonate a wealthier man.

Practise ordinary social conversations because you want to feel more at ease, not because you're trying to defeat the loudest chap at the party.

Improving yourself can be satisfying. It doesn't have to be a war against every other man with a pulse.

Monty, for instance, has put a fair amount of effort into cultivating his magnificent moustache. It would be a shame if he spent every morning resenting somebody else's eyebrows.

09 / FROM THE MONTY FILES

Three Things to Do When You Catch Yourself Comparing

First: name the comparison plainly.

“He's more confident in groups than I am.”

That's an observation. “Therefore nobody will ever want me” is a prediction you've invented.

Keep those two statements separate.

Second: ask what you genuinely know.

Maybe he appears confident during a five-minute conversation. You don't know his full life or how compatible he would be with the woman you're meeting.

Third: return to what's actually happening.

Listen to her answer. Ask a follow-up if you're interested. Share something about yourself.

You're on a date, not sitting on the judging panel of a talent contest.

Repeat that whenever you find yourself drifting into the comparison game. Not because you can stop all unhelpful thoughts overnight, but because you can choose what to do next.

10 / FROM THE MONTY FILES

Don't Compete by Putting Other Men Down

Insecurity sometimes comes out as criticism.

You see a man dressed smartly and call him vain. Another has an expensive car and you call him shallow. A confident bloke talks to a woman and you announce that he's probably full of himself.

Perhaps he is. Perhaps he isn't.

Either way, you're not making yourself more appealing by sneering at strangers.

And don't ask a woman you've just met to reassure you that you're better than other men. She didn't come on a date to referee a dispute between you and the entire male population.

Be curious about her. Let her see your personality. Don't turn another man into a villain so you can feel like the hero.

11 / FROM THE MONTY FILES

When Social Media Makes It Worse

If every scroll leaves you feeling inadequate, change what you're looking at.

Unfollow accounts that seem to exist solely to show off an impossible lifestyle. Stop reading dating advice that divides men into winners and losers based on appearance or income.

You can follow people you admire without using their achievements as a punishment against yourself.

And remember that an attractive woman isn't a prize awarded to the most impressive man in the room.

She's an individual with preferences, boundaries and her own decisions to make.

Nobody gets to “win” her by being taller than his competition.

12 / FROM THE MONTY FILES

What About Rejection?

Here's the awkward truth: sometimes a woman you fancy will prefer somebody else.

It happens. You might be perfectly pleasant, funny and considerate, and she still won't feel a romantic connection.

That doesn't mean the other man is a better human being.

It means two people were interested in each other and you weren't one of them.

You can feel disappointed. You can have an evening of grumbling to your mates. You can decide that dating is a thoroughly unreasonable business.

Then carry on.

A preference is not a worldwide ranking.

You don't have to convince yourself you're every woman's ideal partner. You only need to meet somebody whose interest is mutual and whose company you genuinely enjoy.

13 / FROM THE MONTY FILES

The Monty Verdict

To stop comparing yourself to other men, stop converting individual differences into a verdict on your value.

You don't know every man's life, you don't know every woman's preferences and you certainly don't need to win every imaginary contest you invent.

Look after yourself. Develop the qualities you care about. Enjoy your own friendships and hobbies. And when you're on a date, pay attention to the person who agreed to spend time with you.

Old boy, there will always be a chap with better hair.

There will never be another chap who's exactly you.

That's a much more useful starting point than a scorecard.

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