To keep your confidence after a date that went badly, distinguish the evening's actual events from the sweeping verdict you're tempted to make about yourself. A disappointing evening can mean there was no chemistry, poor timing, a mismatch in expectations or one awkward decision you can improve next time. It does not establish that you're unattractive or hopeless at dating. Look honestly at what went wrong, take one useful lesson if there is one, and allow yourself another chance without trying to become a completely different man.
Some dates are delightful. Others are awkward, badly timed or simply disappointing. Monty has enough questionable jackets in his wardrobe without pretending every failed evening was an epic adventure.
You may come home from a bad date wanting to analyse everything you said and wondering whether you ought to give up. Neither reaction will tell you what actually happened.
First, put the evening in proportion. One meeting with one person cannot stand in judgment over your entire romantic future.
The first thing to know is that a bad date is an event, not an identity. You attended one evening with one woman. The whole of your future romantic life wasn't present to be judged by a jury.
Why did your date go badly? Four different possibilities
“Terrible date” can describe several completely different evenings.
Perhaps she was pleasant but you had nothing in common. Perhaps you enjoyed yourself and she didn't want another date. Perhaps the conversation stalled and neither of you quite knew how to restart it. Perhaps you were both enjoying the meal until you discovered you had very different expectations about relationships.
Those situations shouldn't be treated as the same failure.
Begin with what you could observe. “We struggled to find a shared subject” is something you can work with. “She thought I was boring because my whole personality is defective” is an interpretation, not a witness statement.
If you behaved badly, acknowledge it. If you made a sharp joke that hurt her feelings, apologise without defending the punchline. If you ignored an obvious boundary or spent the meal talking exclusively about yourself, that's worth changing before another date.
But don't automatically take responsibility for a lack of attraction. Two decent people can simply fail to fancy each other. No villain is required.
The evening at the riverside restaurant
Imagine Julian, a man who has been looking forward to a first date but is determined to make every part of the evening impressive.
He'd been looking forward to meeting a woman named Elena. They'd exchanged lively messages about architecture, sailing and their mutual hatred of restaurants that serve an entire meal on a piece of slate. He booked a beautiful little riverside place.
Then he arrived forty minutes early, drank two coffees, discovered his collar was too tight and spent the first half-hour explaining why he'd chosen the restaurant. He told Elena the architectural history of the neighbouring bridge, twice. He asked her almost nothing about herself.
When Elena mentions that she is learning to sail, Julian interrupts with a long story of his own. He never asks what she enjoys about it.
She was polite. She was also ready to go home.
The next morning, Julian might be tempted to conclude that she wanted somebody handsomer, wealthier or more mysterious.
That would miss a more useful possibility: he barely gave Elena a chance to talk about herself.
You cannot know for certain why somebody did not want a second date. But you can notice habits that might make conversations less enjoyable.
Julian does not need a new face or a manufactured air of mystery. He needs to recognise that there is another person at the table.
That was useful information. Far more useful than the conclusion that he ought never to leave the house again.
Don't turn one woman's opinion into a worldwide referendum
You could be cheerful, interested, well dressed and a pleasure to talk to, and she still might not be attracted to you.
That's not necessarily a contradiction. Attraction depends on the two people involved. One woman loves dry humour; another finds it baffling. One prefers a lively room; another wants a quiet corner. Somebody may have realised she's not ready to date at all.
None of this means that preferences are predictable or that a particular type of woman will respond in a particular way. Dating is about meeting individuals, not winning approval from a committee called Women.
If someone says she didn't feel a romantic connection, take her at her word. Resist demanding a detailed explanation of her reasons. An honest “I don't think we're quite the right match” is enough.
And don't decide that the rejection must be a cover story for some terrible private judgement. You're guessing at a mind you cannot inspect.
What to do after a bad date: a useful five-minute review
After a disappointing date, ask three questions.
What did I enjoy? There may have been a good conversation about travel, a new restaurant, or simply the satisfaction of having made an effort. Not every moment needs to be converted into a loss.
What would I do differently? Choose something you can actually influence: asking more questions, finding a venue where you can hear each other, arriving on time or making your intentions clearer.
What wasn't mine to control? Her attraction, her circumstances, whether your senses of humour matched and whether she wanted the same sort of relationship.
Do this once. Five or ten minutes is plenty. Don't set up a tribunal that reconvenes after breakfast, lunch and every time you pass the restaurant.
The distinction matters because a useful lesson leads to different behaviour. Endless replay merely repeats the disappointment.
If a woman mentions a hobby, let her finish and ask a question before turning the conversation back to yourself. That is a practical lesson you can use on your next date.
When you were genuinely embarrassed
Perhaps you spilled your drink, forgot her name momentarily, tripped over a chair or told a joke that landed like a sack of wet cement.
An embarrassing incident can certainly affect a date, but its importance often depends on what follows. If you can acknowledge it lightly and get back to the conversation, the evening may continue quite happily. If you spend forty minutes apologising for an overturned water glass, the glass has effectively become your chaperone.
Try a brief, proportionate response: “Well, that's my dramatic entrance out of the way,” followed by making sure nobody has been splashed and helping put things right.
If you've genuinely inconvenienced or hurt somebody, a sincere apology is appropriate. Humour mustn't substitute for accountability.
But ordinary clumsiness is not a character verdict. Sometimes people laugh together over a mishap; sometimes they don't. Your task is to behave well, not to guarantee a favourable review.
I've a separate discussion about recovering from an embarrassing dating moment, because that calls for quick decisions while the evening is happening. Here we're dealing with what you do after you've come home.
When the problem was an unpleasant date rather than a failed performance
Not every bad date is merely awkward. Perhaps she was dismissive, insulted you repeatedly, pushed your boundaries or made you feel unsafe.
Do not confuse endurance with romantic confidence.
You can politely end a date that isn't respectful: “I don't think this is working for me. I'm going to head off. Take care.” You don't need to finish another course or make a speech about why you deserve basic courtesy.
If the problem involved intimidation or unsafe behaviour, prioritise leaving safely and contacting someone you trust. You are not required to make a joke out of it for the sake of being charming.
A date that reveals incompatibility early has told you something useful. You can feel disappointed while also recognising that continuing would have wasted more of your time.
Should you suggest a second date if the first went badly?
Sometimes. First decide whether the actual connection was worth another try.
If you both enjoyed parts of the evening but the venue was dreadful or the timing unfortunate, it may be reasonable to suggest something simpler: “I enjoyed talking with you despite the world's loudest restaurant. Would you fancy coffee somewhere we can hear each other?”
If she says no, accept it. If she doesn't respond, don't campaign.
And if the first date showed a clear values mismatch, another evening may simply provide a more expensive version of the same information.
Romance is not a contest in which every match must progress to the next round.
What to tell yourself the following morning
Nothing grandiose. Don't declare yourself an irresistible champion who was tragically misunderstood. That's merely the opposite form of the same exaggeration.
Instead, be accurate.
“I was disappointed.”
“She didn't want another date.”
“I could have listened better.”
“We weren't right for each other.”
Those are ordinary sentences. They're not as theatrical as “My romantic future lies in ruins,” but they're far more useful.
You can also have a bad evening without needing to discover a profound lesson. Sometimes the music was too loud, your jokes didn't land and you simply weren't compatible. Fine. Have breakfast.
If it helps, speak to a friend who will tell you the truth with affection. Prefer the one who might say “You did talk about your sports car a little too much” rather than the one who declares any woman who declines you incapable of appreciating your charms.
Flattery is a lovely dessert. It makes a dreadful diet.
Keep your next date from becoming a revenge performance
A surprisingly common mistake is deciding that your next outing must compensate for the last.
You plan a grand entrance. You rehearse jokes. You attempt to appear wealthier, cooler or more experienced than you are. You select a jacket with more ambition than fabric.
This is how a single disappointing dinner turns into the production budget of a small West End musical.
The next woman hasn't met you yet. She deserves to meet you, not a defensive version assembled to impress somebody else who already declined.
Choose a comfortable venue. Wear something that looks good and allows you to sit down. Have a few genuine things you'd enjoy asking about. Make an effort to listen, flirt when it feels welcome and remember that she's deciding whether she likes you while you decide whether you like her.
A good date isn't one where you earn full marks. It's one where two people have the chance to find out whether they enjoy being together.
How soon should you date again after a bad date?
There's no timetable. If you fancy meeting someone else next week, you're allowed. If you'd rather spend a fortnight enjoying your own company, that's equally reasonable.
Don't rush into another date to erase the disappointment, especially if you're still angry at someone who didn't choose you. Equally, don't insist on months of solitary reflection because a stranger didn't find your anecdotes about sailing sufficiently captivating.
Return when curiosity about another person feels stronger than the urge to defend yourself.
A first date should not require a mortgage application, a ball gown or two rehearsals.
Give the next date a new chance
On a later date, try a more balanced conversation: ask what drew her to the exhibition, share what interested you and notice whether you are both enjoying the exchange. If you made a genuine mistake previously, correct that habit. If the two of you simply weren't compatible, there may be nothing to repair. Your next date deserves a fair chance, without carrying the whole of the previous evening into it.
That's how confidence grows after a bad date. Not from denying the disappointment, but from refusing to let a single evening define you.
For more of Monty's cheeky advice on attraction and meeting women, start with my free 14-page 7 Secrets to Becoming a Babe Magnet. You'll find it via the free-guide link on this page, old boy.
And for heaven's sake, if the restaurant serves fish on a roof tile, don't let that alone ruin your evening. It's still possible to meet somebody marvellous over an absurd piece of slate.