To recover from an embarrassing dating moment, acknowledge what happened briefly, put right anything you've spoiled, and return your attention to the person you're with. A spilled drink, an unfortunate joke or a forgotten name doesn't have to ruin a date. Apologise properly if somebody has been inconvenienced or hurt; otherwise, a little humour and a change of subject can help the evening continue. The mistake usually becomes more awkward when you keep explaining it long after the moment has passed.
I should disclose that Monty has personal experience with the subject.
There was an evening in May, some years ago, when I escorted a ravishing woman named Amelia to a country-house dinner. I intended to make a restrained, sophisticated entrance. Unfortunately, a low marble step, an antique umbrella stand and the extravagant cut of my trousers formed a small alliance against me.
I entered the drawing room sideways, carrying an umbrella I did not own, with a silver shoehorn caught in my cuff.
“Monty,” said Amelia, “is that part of the dress code?”
“Only for men of considerable imagination.”
We laughed. I returned the umbrella, retrieved the shoehorn and asked whether she'd seen the terrace.
That was the entire recovery. No lengthy defence of my tailoring. No demand for reassurance that she still found me attractive. Just a ridiculous incident, briefly dealt with.
There are times, however, when the right response requires more care than a wisecrack. Let's distinguish them.
First, work out what sort of mistake you've made
A date's embarrassing moments generally fall into three groups.
The harmless mishap: a knocked glass, a missed step, a muddled sentence, food on your shirt. Somebody might laugh, but no real harm has been done.
The awkward social misjudgement: you talk over her, make a joke she doesn't understand, overdo a compliment or misread the mood. You may need to acknowledge it and adjust.
The genuine offence: you say something hurtful, ignore a clearly expressed preference or make her uncomfortable. That calls for a sincere apology and changed behaviour, not an attempt to charm your way out of responsibility.
Knowing which one you're dealing with prevents two opposite mistakes: apologising for half an hour because you dropped a fork, or grinning through a moment when you should plainly say sorry.
If you aren't sure how your remark landed, ask with consideration: “I think that came out badly. Did I upset you?” Listen rather than defending your intentions before she's answered.
The spilt drink: deal with the mess before the joke
Suppose you reach for your glass and accidentally send a splash of wine across the table.
First check whether anybody is wet, whether clothes or belongings have been affected, and whether the staff need to help. “I'm sorry, that was clumsy of me. Let me get that sorted” is far more useful than a nervous twenty-minute speech.
If you have damaged something, offer a sensible remedy. If it's a minor spill, help clean up and take your cue from her.
Then, if the moment is light enough, you can smile. “Excellent. I've managed to christen the table before the main course.” Don't make a joke at her expense if she's wearing the wine.
Afterwards, resume the conversation. Ask about the story she was telling before the accident. You demonstrate confidence by handling an inconvenience properly and remembering that she's still the point of the evening.
A man who behaves well when something goes wrong is providing a glimpse of his character. That can be more revealing than the polished opening compliment he'd spent half an hour choosing.
When the joke lands with a terrible thud
Humour is an imperfect art. I know this because I have personally delivered jokes so magnificent that the recipients required several days to appreciate them. At least, that's the explanation I favour.
Suppose you make a playful remark about her favourite television programme and she looks puzzled rather than amused.
Don't repeat the joke louder. Don't explain the punchline in the manner of a lecturer demonstrating a faulty washing machine. And don't insist that she hasn't understood your highly advanced sense of humour.
Try a gentle acknowledgment: “I suspect that joke sounded better in my head.” Then return to what she was saying: “You were telling me why you love the programme — go on.”
If the joke was personal or unkind, be more direct: “Sorry, that was unfair. I shouldn't have said it.” Leave room for her response.
A difference in humour doesn't automatically mean the date is doomed. Sometimes two people need time to understand each other's style. Sometimes their styles simply aren't compatible.
Your job isn't to force her to laugh. It's to make conversation enjoyable for both of you.
You said the wrong name. What now?
Ah. A particularly unfortunate moment, and one where glibness seldom helps.
If you've just met and muddle her name with another new acquaintance, correct yourself promptly: “I'm sorry — Anna, not Emma. I got that wrong.” Then make a proper effort to remember it.
If you call her by an ex-partner's name, it's more delicate. Acknowledge the mistake without telling a five-minute story about the ex. “I'm really sorry. That was careless, and I understand why it might have bothered you.”
She may laugh it off. She may not. Either response is hers to have.
Do not attempt to persuade her that the mistake was secretly flattering, or that you only used the name because she's similarly beautiful. There are occasions when a gentleman's improvisational gifts should remain firmly in their box.
Names matter. Learn them, use them naturally and don't treat someone else's embarrassment as an inconvenience she should immediately forgive.
When you go completely blank
You're midway through an amusing account of a holiday, she smiles, and your brain decides to take an unscheduled afternoon off.
There's no need to fabricate a dramatic ending. You can say, “I've completely forgotten where that was going. Clearly the wine has staged a coup.” Then ask her a question or move to another subject.
If you've forgotten a particular detail, be honest. “I can't remember the name of the place, but it was by the coast” is sufficient.
Don't panic and fill every second with unrelated trivia. Silence is an ordinary part of conversation. She may be thinking of something to say herself.
Look for an easy route back: the last thing she mentioned, the shared surroundings, or something you genuinely want to know about her.
The best conversational partner isn't the one who never falters. It's the one who can make a little room for another person.
When your attempt at flirting was too much
This deserves special attention, because the stakes are different from tripping over a chair.
Suppose you've leaned in for a kiss and she turns away. Or you've made a suggestive joke and she appears uncomfortable. The right response isn't to press ahead, complain that she led you on or ask repeatedly whether she's sure.
Give her space immediately. “Sorry, I misread that” is plenty. Respect the boundary without making her responsible for soothing your embarrassment.
The same applies if you've moved too close, touched her arm and she pulls back, or persisted with a flirtatious subject she doesn't seem to enjoy. Stop. Let the conversation return to something comfortable if she wants to continue.
You haven't ruined your dignity by accepting a boundary. On the contrary, handling a misunderstanding respectfully is exactly what dignity looks like.
And if she's no longer interested in continuing the date, accept that as well. There is no clever line that converts a clear no into an invitation to negotiate.
Monty is very fond of boldness. I am rather less fond of boorishness.
Stop apologising once you've actually apologised
A sincere apology can mend an awkward moment. Ten apologies can turn it into the main event.
If you say, “I'm sorry I interrupted you — please finish,” and she continues her story, listen to it. Don't interrupt again five minutes later to ask whether she's still annoyed about the original interruption.
Repeated reassurance-seeking puts an uncomfortable burden on the other person. She may feel she has to spend the rest of the meal convincing you that you're a decent fellow instead of enjoying herself.
Make the apology proportionate to what happened, take any practical action needed and let the evening move on if she is ready.
Of course, if the mistake was serious, she may not feel ready. You cannot insist that your apology must restore the mood. Listen, respect her decision and accept the consequence.
The rule is simple: say sorry to make things right, not to extract a guarantee that you're still attractive.
How to read her response without making up a verdict
If she laughs with you after an ordinary mishap, that may be a sign she feels comfortable. If she seems distracted, it may mean something else is on her mind. If she's upset, take it seriously.
Don't turn a single expression into a prediction of the rest of the evening.
Watch what happens after you recover. Does the conversation resume? Does she ask another question? Is she still engaged? Those are more useful indications than the one second in which she stared at your fallen fork.
If she seems uncomfortable and you don't know why, a considerate question is fine. If she says she'd like to leave, don't pressure her to stay.
You aren't auditioning before a panel whose judgement must be accepted without appeal.
What to do in the next five minutes
Here's the useful sequence, not a ritual to memorise but a way to keep your head when your champagne glass develops wings.
Deal with the immediate issue. Clean the spill, return the object, correct the name or stop the unwanted advance.
Acknowledge what happened in a tone appropriate to its seriousness. A harmless mishap might invite a smile. A hurtful remark requires a proper apology.
Then turn your attention back to the evening. Ask about the thing she was telling you. Suggest returning to the exhibition. Continue the walk if she wants to.
If you need a moment, it's fine to take it. You aren't required to produce instant charm like a vending machine dispensing compliments.
And do not try to rescue the moment by spending money. Ordering expensive champagne because you stumbled over a word merely provides a more luxurious setting in which to stumble again.
Should you mention it afterwards?
Usually not, if it was harmless and forgotten. You don't need to send a post-date message apologising for the exact angle at which you knocked over a napkin.
If you enjoyed the evening, say that: “I had a lovely time. I'd enjoy seeing you again.”
If you genuinely hurt her feelings, an appropriate follow-up apology may be worthwhile, particularly if she didn't have the chance to discuss it at the time. Keep it direct and give her room to respond or not.
If you aren't offered another date, don't assume the embarrassing moment explains everything. A lack of romantic chemistry can have nothing to do with the incident you keep replaying.
You can learn from a mistake without appointing it the official historian of your love life.
For longer-term confidence after a generally disappointing evening, see my separate guide to keeping confidence after a bad date. This one is about the split second when something goes wrong and what you can do next.
Monty's final word on public humiliation
At that May dinner, Amelia asked whether I'd enjoyed the evening.
“Enormously,” I said. “Although I seem to have acquired a shoehorn.”
She laughed, took my arm and suggested we see the gardens before dessert.
I don't recommend deliberately getting caught in antique furniture as a flirtation strategy. It's costly, undignified and remarkably hard on one's cuffs.
But I would recommend handling the unexpected with kindness, proportion and a little good humour where it's welcome. That's more appealing company than a man who insists every moment must be perfect.
If you want more of Monty's advice on making a better impression and meeting women with confidence, my free free 14-page guide to becoming a more charming date guide is available through the free-guide offer on this page.
Remember: even if you arrive at dinner wearing half the flower arrangement, you're still allowed to have a wonderful evening.