You've chosen a good shirt, practised a few stories and arrived determined to be charming. By the starters you're exhausted. There's a better way, old boy.
To stop treating dates like a performance, give up the idea that you have to impress a woman for an entire evening. Prepare the practical details, then concentrate on whether you actually enjoy her company. Ask questions you're interested in, answer honestly, let small mistakes happen and stop reviewing every sentence in your head. A date is a meeting between two people, not an audition in which one person does all the work.
I've met men who can chat perfectly well to anybody until they fancy somebody.
Then something extraordinary happens.
They become a contestant on a talent show nobody else knows is taking place.
The jokes come out. The anecdotes have rehearsed punchlines. They agree with opinions they don't agree with. They laugh at things they don't find funny. And when they return home, they begin evaluating the evening as though they've just completed a job interview for the position of Boyfriend, Grade Three.
Monty understands the impulse. I wouldn't own aviator sunglasses and a gold medallion the size of a dinner plate if I were entirely immune to making an entrance.
But there is a difference between making a little effort and building an entire character for a woman to meet.
The Question That Changes the Evening
Before you go on your next date, replace one question.
Instead of asking, “How do I get her to like me?” ask: “Do we enjoy each other's company?”
That second question includes you.
It doesn't mean you become selfish or stop caring what she thinks. You still turn up on time, listen, practise good manners and behave respectfully.
But your own curiosity matters too.
Do you enjoy her humour? Are you interested in her stories? Do you feel comfortable expressing a different opinion? Would you want to spend another afternoon together if there were no grand romantic story riding on the outcome?
You cannot answer those questions when you're spending all your energy trying to deliver an impressive performance.
When a man is desperate to be liked, he can walk away from a date knowing exactly what restaurant she prefers and almost nothing about whether he enjoyed himself.
A rather expensive way of forgetting you're also part of the equation.
Prepare the Date, Not the Character
There are sensible things to sort before meeting.
Check the venue is open. Know how you're getting there. Make sure you've got enough money for the plan you've agreed. Wear something clean and comfortable. If you said you'd book a table, actually book it.
Marvellous. You're prepared.
Now resist the temptation to script the evening.
Don't memorise a dozen “perfect” anecdotes and plan precisely when to deploy each one.
Don't practise an alluring laugh in the mirror. That's a very strange business, even by Monty's standards.
Don't decide beforehand which hobbies will make you seem most desirable.
You might spend half the evening guiding her towards a story about sailing, only to discover she's terrified of boats and would have been much happier hearing about your disastrous attempt to cook risotto.
Have things in your life worth talking about, certainly. But let the conversation decide which ones come up.
Stop Monitoring Yourself While She's Speaking
This is where the performance habit does real damage.
She's telling you about a funny day at work.
Meanwhile, you're thinking:
Am I making enough eye contact? Did that joke sound stupid? Does my shirt fit properly? Should I ask another question? Am I talking too much? What if this silence means she doesn't fancy me?
She finishes her story.
You realise you've missed the ending.
That's the moment to move your attention away from yourself.
Ask what happened next. Notice whether she's amused, annoyed or excited by what she's describing. React to the actual story.
If you missed a detail, you can admit it: “Sorry, I lost the thread for a second. What did your colleague say?”
That's better than nodding thoughtfully while having no idea whether she's talking about a promotion or a lost sandwich.
Being interested is easier than looking interested because it gives you something real to do.
A First-Date Example: Two Versions of the Same Man
David meets Rachel for dinner.
He's nervous, which is normal. He wants the evening to go well.
The performance version
Rachel: “I love going to little art galleries.”
David remembers an article saying cultured men are attractive.
David: “Absolutely. I'm very passionate about art.”
Rachel: “Who's your favourite painter?”
David's brain immediately leaves the premises.
He talks vaguely about “the classics,” changes the subject and spends the next ten minutes worrying that he's been exposed as a fraud.
The honest version
Rachel: “I love going to little art galleries.”
David: “I'll admit I know very little about art. I've been to a few exhibitions, though. What makes one worth visiting for you?”
Rachel: “I love the smaller places where you can talk to the artists.”
David: “That sounds more interesting than the big galleries I've wandered through pretending to understand everything.”
She laughs.
Now she's explaining something she enjoys, and David has something genuine to say about it.
The second David hasn't tried to pass himself off as an art expert. He's asked a good question, made her laugh and given her a chance to know the real man.
You Don't Have to Agree With Everything
Imagine she says she loves camping.
You hate camping.
A man putting on a performance might announce that he loves camping too, then spend six months regretting the day he pretended that sleeping on rocks was a lifelong passion.
Try a lighter, more honest response.
“I admire people who enjoy it. My idea of roughing it is a hotel without decent breakfast options.”
She laughs and says you're missing out.
“Go on, then. What do you love about it?”
Now you can disagree and still enjoy each other's company.
Obviously, there's a difference between a playful disagreement about tents and a genuine disagreement over something important, such as wanting children or where you plan to live.
But even then, compatibility matters more than manufacturing agreement.
The point of dating is not to win somebody's approval by concealing every difference.
It's to find out whether the differences you have can sit comfortably alongside the things you share.
What to Do When Your Joke Falls Flat
You make an observation about the restaurant. It sounded hilarious in your head. She doesn't laugh.
A performing man might immediately tell a second joke, then explain the first one, then apologise repeatedly for his supposedly ruined charm.
An ordinary man might smile and say, “Well, that sounded funnier in my head.”
Then ask whether she's been to this restaurant before.
That's all.
People tell bad jokes. They trip over words. They mispronounce menu items. Sometimes they accidentally wave at someone who was greeting the person behind them.
None of this is fatal.
If the joke was genuinely rude, apologise properly. But if it simply wasn't funny, let it die with dignity.
Monty has delivered many heroic one-liners to an audience of absolutely nobody. The world carried on.
When You're Trying Too Hard to Look Confident
Confidence isn't the ability to appear relaxed in every photograph or dominate every conversation.
On a first date, you can say you're a little nervous if it's true.
“I haven't been on many first dates lately. Lovely to finally meet you.”
You don't have to follow that with twenty minutes explaining how anxious you feel.
Just admit it and carry on.
Perhaps she feels the same. Perhaps she's perfectly at ease. Neither is a problem.
The performance trap says you must hide anything that makes you human. That can include nerves, enthusiasm, embarrassment and genuine affection.
But if you're interested in someone, you eventually want her to get to know you, not an actor playing the role of Man Who Has Never Been Nervous.
Stop Turning Every Pause Into a Failure
You're both eating. The conversation stops for a few seconds.
You begin searching your mental catalogue for fresh material.
What about her favourite holiday? Her siblings? Whether she prefers tea or coffee? Perhaps a bold question about the meaning of life?
Old boy, she's trying to enjoy a forkful of pasta.
Not every silence needs filling.
If the pause feels comfortable, let it happen. You can look around, sip your drink or enjoy a moment without talking.
If it begins to feel stuck, pick up something she said earlier: “You mentioned you were thinking of changing jobs. What appeals to you about the new role?”
Or share a brief story of your own.
Silence isn't an automatic verdict on the evening. It can simply mean you've finished one subject and haven't started the next.
The Trap of Having a “Winning” Dating Persona
Perhaps you've watched videos promising to teach you the exact personality women want.
You decide to be more mysterious. More dominant. More detached. Funnier, but never silly. Interested, but never too interested. Confident, but somehow indifferent.
By the time you've absorbed all those contradictory instructions, it's a wonder you can choose a starter without consulting your notes.
Here's the problem: if your performance succeeds, what happens next?
She wants to see that version of you again.
Can you keep pretending to love hiking, hate romantic films, own a speedboat and never need reassurance?
Probably not.
It's exhausting for you and unfair to her.
Making an effort is attractive in its own right. Making up a personality is an expensive way to arrange a second date with somebody who hasn't met the real man yet.
Three Small Changes That Make a Date Feel Less Like an Audition
1. Ask things you genuinely want answered
Instead of firing off questions because you've read they're good for conversation, find something you care about.
She says she used to live abroad.
“What brought you home?”
She mentions learning the piano at forty-five.
“What made you decide to start?”
The difference is that you're curious about the answer.
2. Offer a little of yourself
If she asks what you enjoy doing at weekends, don't give the answer you imagine a glamorous man would give.
If you love gardening, say so. If you build model railways, wonderful. If you spend Saturday mornings watching football, that's part of your life.
Tell her why you enjoy it.
You might discover shared interests. You might discover she thinks football is the world's strangest use of ninety minutes.
Either way, you're learning something.
3. Let the date be ordinary
It doesn't need a spectacular story, a flawless joke or a moment worthy of a film trailer.
You can have a lovely evening discussing holidays, family, favourite meals and the dog that keeps stealing your socks.
Romance isn't always announced by fireworks. Sometimes it begins because being around somebody feels easy.
When the Date Isn't Going Brilliantly
Here's a possibility dating advice often ignores: perhaps you aren't enjoying yourself.
Maybe she's rude to the staff. Maybe she shows little curiosity about you. Maybe your senses of humour are completely different. Maybe you're simply not clicking.
If you're stuck in performance mode, you'll keep trying to impress her regardless.
But it's perfectly reasonable to decide that the connection isn't right for you.
Stay polite. Finish the agreed activity or end things courteously if you need to. You don't owe someone another date merely because you've spent money on dinner.
And she doesn't owe you another date because you've tried hard to be charming.
A date isn't a success or failure examination. Sometimes its value is discovering that two people aren't well suited.
Don't Give Yourself a Marks-Out-of-Ten Review Afterwards
The date ends. You travel home.
A few minutes later you're replaying everything.
At 7:14 you made her laugh. At 7:31 you stumbled over a sentence. At 8:05 you said something about your sister that might have sounded odd.
You could spend three days assembling an evidence file.
Or you could ask three more useful questions.
Did I enjoy her company?
Did the conversation feel reasonably mutual?
Would I like to see her again?
If yes, say so.
“Had a lovely evening. I'd enjoy doing that again if you would.”
If she says yes, splendid. If she doesn't, accept it without turning the night into a referendum on your worth.
You don't have to reconstruct every minute to make sense of a simple answer.
A Better Way to Think About the Second Date
If you arrange another date, don't tell yourself that you must now deliver a better performance.
You are not a comedian whose first show got a four-star review and now needs a standing ovation.
Choose something you both enjoy. Remember a detail from the first meeting. Let the conversation pick up where it naturally left off.
If you were nervous the first time, you may feel more comfortable because you recognise each other now.
And if you still feel a little fluttery, that's not necessarily a problem.
You can like a woman without needing to prove yourself every time you meet.
What If You've Always Felt the Need to Impress People?
Sometimes the performance habit isn't confined to dating.
You may do it at work, with friends or around anybody whose approval you value.
If that's familiar, practise being more honest in ordinary low-pressure conversations.
Admit when you don't know something. Say which film you actually enjoyed. Allow a harmless mistake to go uncorrected without making a speech about it.
If you find that fear of judgment seriously affects your life, support from a qualified professional can help. You don't have to solve every deeply rooted worry by forcing yourself through stressful dates.
For many men, though, the first practical improvement is simply to stop treating every social encounter as a test to pass.
Monty's Verdict
To stop treating dates like a performance, stop auditioning for a relationship and start discovering whether one is possible.
Make an effort with the practical details. Turn up looking and feeling reasonably comfortable. Listen properly. Offer honest opinions. Laugh at yourself when something silly happens.
She gets to decide whether she likes you. You get to decide whether you like her.
Neither person needs an Oscar-worthy performance to earn the right to a second meeting.
Monty may have a magnificent medallion, old boy, but even he knows you can't build a relationship with somebody who's only met the costume.