To enjoy dates without rating every little mistake, pay attention to the conversation you're actually having instead of keeping a mental score of your jokes, appearance and timing. If you spill a drink, lose your words or tell a joke that doesn't land, make any necessary repair and return to getting to know her. Afterward, ask whether you enjoyed each other's company rather than awarding marks to individual moments. A good date is not one where nothing goes wrong; it's one where two people are free to be real together.
Monty has encountered a man with a rather unusual habit. He returns from every date and awards himself points.
Arrived on time: eight. Made her laugh: nine. Failed to remember the name of her dog: three. Accidentally ordered the soup while intending to ask for a pudding: minus twelve and the immediate resignation of his romantic ambitions.
At the end of a perfectly pleasant evening he decides he's scored only sixty-two, which apparently isn't enough to see the woman again.
I should explain that there is no actual governing body for romantic examinations. If there were, I would refuse to attend its meetings on principle and probably steal the ceremonial bell.
Our imaginary gentleman, Nicholas, is allowing his own little scoreboard to become more important than the lady sitting opposite him.
Throw away the scoreboard while the date is happening
A date involves talking, listening, finding things amusing, discovering differences and sometimes wondering whether the waiter has forgotten you.
These events aren't individual tests.
Suppose you tell her about a peculiar holiday mishap and the ending receives only a polite smile. You may conclude that you've failed at humour. But perhaps she was thinking about something else. Perhaps the story wasn't particularly funny. Perhaps you will both laugh at something completely unexpected five minutes later.
You don't need to settle the meaning of every response.
Listen to her next question. Maybe she wants to know where you went. Perhaps she tells her own travel story. The conversation is continuing, which is considerably more useful than knowing whether your joke deserved a seven.
If you begin monitoring yourself, redirect your attention towards something real: what she just said, what you genuinely think, or whether you'd like to hear more.
No grand internal speech required. You have a date to enjoy, old boy.
7.10 pm — silence, apparently minus five
Nicholas discovers that between courses there is a moment when neither person talks.
He marks himself down.
What could be more absurd? A pleasant evening can contain the sound of cutlery. You may both be enjoying the view, considering a menu or simply savouring a very good glass of wine.
A conversation that never pauses would require the stamina of a pair of auctioneers.
If the moment feels natural, leave it alone. Smile. Enjoy the surroundings.
If you'd like to restart the conversation, use something she's already mentioned. “You said you grew up beside the sea. Do you miss living there?” is easy to answer if she wants to continue.
Don't announce that the silence has ruined the evening. Nor must you produce a joke every time the air grows still.
The most relaxed people to spend time with are often those who allow the evening to have its own rhythm.
A pause isn't a verdict. It's what happens between words.
7.25 pm — the olive scores an own goal
Imagine a woman named Beatrice is telling Nicholas about a ridiculous childhood pet. He reaches for an olive. It escapes his fork, arcs across the table and lands squarely in his lap.
What next?
He can smile, retrieve the olive and perhaps remark, “That one appears determined to leave the country.” If he has made a mess, he can apologise to anyone inconvenienced and help put it right.
Then he can ask what the pet did next.
The poor olive needn't become the central incident in a romantic inquest.
A gentleman who insists on explaining that he is usually excellent with cutlery may accidentally make the mishap much more memorable than it was.
You don't have to recover with a brilliant line, either. A simple “Well, that went badly” followed by a laugh is human enough.
Mistakes happen. Your response can show humour, care and consideration, but even that doesn't need a score.
Perhaps she drops something later. Give her the same easy courtesy you'd like for yourself.
7.30 pm — one mistake that actually matters
There is an important difference between dropping an olive and making somebody uncomfortable.
If you interrupt her repeatedly, make a joke at her expense or realise you've been dismissive, don't wave the error away merely because you want to appear relaxed.
Say something specific: “I'm sorry, I cut across you. Please finish your story.”
Or, “That joke was unfair. I shouldn't have said it.”
Then listen, adjust your behaviour and let her decide how she feels.
You haven't ruined the evening by acknowledging a mistake. Equally, a real apology doesn't entitle you to immediate forgiveness.
The point of abandoning the scoreboard is not to avoid responsibility. It's to focus on how the exchange is actually unfolding.
If she's happy to continue, allow the conversation to develop. If she's not, respect her choice.
Being a good date is about consideration and shared pleasure, not carefully maintaining an image of never having been wrong.
That image is both exhausting and thoroughly unconvincing.
7.45 pm — the opponent at the next table
Nicholas has also devised a secret scoring system for his clothes.
The jacket looked magnificent at home. Now he worries that the shoulders are too broad. He catches a reflection in the restaurant window and decides his hair is incorrect. He compares himself with a fellow at the next table and awards the stranger several unsolicited points.
None of this tells Nicholas whether Beatrice finds him attractive.
He has made an effort. He is wearing clothes he likes. She has agreed to meet him, and there is a conversation he could be enjoying.
If she compliments his jacket, he might simply thank her. If she doesn't, there is no need to solicit a review.
And if he happens to notice that she's wearing a lovely necklace, he can compliment it naturally without treating his own appearance as a bargaining chip.
A date is not a competition with the other men in the room.
The fellow two tables away is probably trying to work out whether his fish contains bones. Leave him to his dinner.
Stop reviewing yourself after every question
She asks whether you've travelled much. You describe a wonderful weekend in Edinburgh, then immediately wonder whether it sounded too ordinary.
She asks about your work. You explain what you enjoy about it, then worry that you seemed too enthusiastic.
You can't participate fully in a conversation while simultaneously supervising each sentence like an impatient producer.
Give your answer. Let her respond.
If she asks a follow-up, you're learning what interests her. If she changes the subject, you can follow. If she offers an opinion you disagree with, the two of you may enjoy a little debate.
The exchange creates information you couldn't possibly have obtained by rehearsing alone.
Don't demand that every answer make you look outstanding. Sometimes the most appealing thing about a man is that he's genuinely interested in a subject and enjoys sharing it.
A woman can fancy a fellow who gets slightly carried away describing an antique car. She may also decide that subject bores her. You won't discover either by continually editing yourself.
When your date makes a mistake
Now imagine Beatrice confuses the name of a band and tells an anecdote with a rather tangled ending.
Nicholas can respond kindly, laugh with her when she laughs at herself, or ask a question that helps him understand the story.
He doesn't need to collect evidence that she is less impressive than he hoped.
This cuts both ways. If you expect generosity for your small errors, offer some in return.
A woman may be shy at the beginning, become wonderfully animated later or make a silly remark that neither of you repeats. She deserves to be met as a whole person too.
Of course you can notice genuine incompatibility, unkindness or repeated behaviour that bothers you. A date is partly about making judgements. But those judgements should concern real patterns and how you both feel, not a tally of trivial stumbles.
If she treats the waiter badly, that may tell you something significant. If she mispronounces the name of a pudding, it probably doesn't.
Monty draws a very firm line between poor manners and imperfect custard pronunciation.
Don't let the good parts disappear
At the end of the evening, Nicholas remembers the olive, one quiet moment and an unfortunate remark about the weather.
What he forgets is that Beatrice told him a hilarious story about the family dog, asked thoughtful questions and laughed at his favourite ridiculous film.
He also forgets that he enjoyed listening.
If you find yourself analysing the date afterwards, start with the larger experience.
Did conversation feel mutual? Were you comfortable being yourself? Did she seem comfortable too? Did you genuinely want more time together? Were there any actual concerns worth addressing?
You can answer those questions without spending an hour examining the precise timing of an eyebrow.
If you enjoyed the evening, say so. “I had a lovely time. Would you fancy meeting again next week?”
If you didn't, a polite goodbye is enough. You are allowed to want a different connection.
Either answer is more meaningful than the self-awarded mark for an early joke.
How to respond when she points out a little blunder
Perhaps Beatrice laughs and says, “You have called this restaurant the wrong name three times.”
Nicholas can grin. “At least I've found the right table.”
That's good humour if she is teasing affectionately.
If she sounds genuinely annoyed because he's forgotten something important, he should listen and take the point. Repeatedly making light of another person's concern is not charm.
The distinction is in the situation, not in an official manual of how jokes must be received.
You can ask, “Did that bother you?” if you're uncertain and the detail matters.
What you don't need is a lengthy explanation of your intention followed by an appeal for full reinstatement of your romantic grade.
Sometimes you learn; sometimes you laugh; sometimes you both move on.
And the charming thing about a genuine connection is that both people can allow those ordinary moments to happen without calling a committee.
A second date is not an exam retake
Here's a subtle danger. Nicholas finally secures another evening with Beatrice and decides he must correct every mistake from the first.
He rehearses a much better holiday story. He memorises the dog's name. He selects a restaurant where olives are less likely to escape.
There's nothing wrong with remembering her dog's name. It's kind to pay attention.
But don't approach the next date as an attempt to achieve the hundred points you missed last time. She agreed to see you again because she wants another opportunity to spend time together.
You can propose an outing you both enjoy, tell a new story and discover more about her.
Perhaps you'll make an entirely different small mistake. Perhaps she will. If either happens, life will continue and somebody may even have a good laugh.
The purpose of another date is to deepen a possible connection, not improve your official ranking in a competition that does not exist.
Full time — and nobody was keeping score
At their next dinner, Nicholas starts to reach for an olive and hesitates.
Beatrice notices and smiles. “Go on. I dare you.”
He takes it, successfully, with all the grandeur of a man who has just conquered the Mediterranean.
She laughs. He laughs. And for once he doesn't wonder how many points he's earned.
The evening is not perfect. It is theirs.
If you want to enjoy dates without rating every little mistake, stop watching yourself as though you were the only performer on stage. Join the conversation, make a genuine invitation, treat errors with proportion and notice whether the two of you like one another.
The olives, meanwhile, should be allowed their personal freedom. Some are clearly destined for adventure.