Making a woman laugh on a date is about sharing amusement, not performing stand-up. Listen for the funny parts of a story, tease yourself gently and notice what sort of humour she enjoys. If a joke doesn't land, don't force it; a relaxed, curious conversation is far more valuable than being funny every minute.
I have a considerable weakness for people who make me laugh. Not just the grand, theatrical belly laughs that leave you bent double over your dinner, but the little conspiratorial ones. The shared glance when somebody at the next table makes a spectacular fuss about the temperature of a potato. The quiet amusement when you both recognise that an earnest television advert is talking complete cobblers.
That's the lovely thing about humour on a date. At its best, it says: We're seeing the same wonderfully ridiculous world, at least for a moment.
Unfortunately, tell a nervous man that women find humour attractive and you may inadvertently create an amateur stand-up comedian. He arrives armed with fourteen jokes, a carefully rehearsed impression and an anecdote about a stag weekend that has been timed to the second. If the first gag fails, he immediately launches a second, as though the date has become a sinking ship and laughter is the only available lifeboat.
Let's retire that approach. You don't need to be the funniest man in Britain. You need to enjoy the conversation, notice the funny bits and give both of you permission not to take yourselves too seriously.
First, understand what she's actually laughing at
Not every laugh is the same. People laugh because something is funny, because they're delighted, because they're nervous or because they're being polite. If she chuckles when you make a remark, splendid, but don't treat it as proof that Cupid has personally approved your application.
There is interesting research here. Studies of speed dating have found links between perceived funniness and attraction, while other work has examined how couples laugh together. The results aren't a universal law, nor do they show that delivering more jokes guarantees anything. What they suggest, rather modestly, is that humour and shared enjoyment can matter in romantic connection.
The distinction I care about is between performing comedy at someone and finding things funny together. The first leaves her sitting in the audience. The second makes her a participant.
If she makes a joke, enjoy it. If she's being playful, play along. If her humour is dry, notice that rather than bringing out your loudest pub routine. The chemistry sits in the exchange, not in your ability to command the room.
Observation beats memorised material
A borrowed joke has a peculiar problem: even when it's funny, it doesn't necessarily tell her much about you.
Observation, on the other hand, happens right there. The waiter solemnly introduces a plate containing a single carrot and seven dots of sauce. Your menu describes the chips as "a deconstructed potato experience". A dog outside the café is staring through the window at your breakfast with the expression of a tax inspector.
You needn't make a speech. A quietly delivered "I think he's auditing the sausages" might be enough to make you both grin.
Of course, this requires restraint. The world provides plenty of material, but another person doesn't exist to be mocked for your entertainment. Be amusing about the situation without being cruel to the staff, the other customers or someone who cannot defend themselves.
A good observation often succeeds because it is small and spontaneous. Don't spoil it by explaining why it was funny. If a remark receives no laugh, simply carry on. Your honour has not been stained.
Let her be funny too
This sounds obvious, yet it might be the most frequently overlooked piece of advice in the whole business.
A man desperate to impress can monopolise every funny moment. She begins a story about a disastrous holiday, and he interrupts with his own better, louder, more catastrophic version. She offers a witty remark, and he immediately tops it. By dessert, she's not on a date so much as attending a comedy battle she never entered.
Give her the floor. Ask how her story ended. Laugh when something genuinely delights you. Return to a funny detail later if it becomes a shared reference.
If she says that her family once accidentally took somebody else's suitcase on holiday, don't instantly launch into your ten-minute airport anecdote. Ask what was inside it. A surprising answer might be far funnier than anything you could have planned.
People like being enjoyed. Being the only funny person in the room is a lonely achievement, and a poor foundation for romance.
A little self-mockery is charming; self-destruction isn't
I often recommend a light touch of self-deprecation, particularly for men who worry that confidence means acting invincible.
If you confidently select a wine and discover you've been pointing at the dessert list, you can laugh at yourself. If you take the wrong turning on the way to a café, admit that your internal compass was apparently purchased from a jumble sale.
The useful quality here is ease. You aren't frightened of looking momentarily foolish.
But keep the criticism gentle. Constantly calling yourself ugly, boring, stupid or undesirable puts her in the awkward position of having to reassure you. "I'm hopeless with directions" can be funny. "No woman ever likes me, I'm an absolute loser" is not the sparkling conversational contribution you imagine.
Nor should self-deprecation become a way of asking for compliments. If you repeatedly insist your outfit is dreadful in the hope she'll contradict you, you are simply fishing with a sad little rod.
Have enough confidence to survive your own small mistakes. That's the amusing part.
Teasing only works when you're both in on it
Playful teasing can produce wonderfully flirtatious chemistry. It can also go wrong with astonishing speed.
Suppose she says she loves a dreadful old pop song. If you both share the same cheeky style, you might announce that you will require a formal explanation before proceeding with the date. She laughs, defends the song and takes a light-hearted swipe at your musical taste. Splendid. You're playing together.
Now imagine you keep ridiculing her tastes after she stops finding it funny. You've moved from flirting into being a bore with an unnecessarily sharp tongue.
Never use insecurities as material. Her body, age, background, income and previous relationships aren't props for your entertainment. Avoid disguising an insult as a joke and then blaming her for lacking humour if she doesn't laugh.
The easiest test is reciprocity. Is she teasing back? Does she seem relaxed? Is she laughing freely rather than offering a tight smile? If not, move on. Good flirting is responsive. It doesn't require winning a contest.
Your funniest story probably needs editing
Everybody has a favourite anecdote. Mine might involve a ruined dinner party, an elderly neighbour and an ornamental fountain. Yours may involve a friend's wedding where the cake arrived on the wrong day. The temptation is to describe every detail because you were there and you know how marvellous the ending was.
Your date wasn't there. She doesn't need the full cast list, the travel arrangements and the precise sequence of events leading up to the incident with the trousers.
Give her the setting, the problem and the funny detail. Let the rest go.
And for goodness' sake, notice whether she's engaged. If she's asking questions and laughing, continue. If she's been staring at her drink for three minutes while you explain the layout of an unfamiliar motorway service station, consider landing the plane.
The purpose of a funny story is to share enjoyment, not establish the historical record for a future parliamentary inquiry.
Don't use humour as armour
There's another trap, quieter than the amateur comedian and rather more common in otherwise charming men. Every time the conversation threatens to become sincere, they crack a joke.
She asks what you're looking for in a relationship. You answer that you're mainly seeking someone willing to share their chips. She asks about your family. You tell a funny story about your brother. She mentions something difficult that happened last year. You try to cheer her up with another gag.
Humour can ease tension, but if it's the only instrument you play, she may never find out what matters to you.
You can be playful and direct. "I enjoy dating, but I'd really like to meet someone I connect with" is a perfectly reasonable answer. When she says something serious, listen before reaching for a punchline.
The ability to change tone comfortably is more attractive than keeping the entertainment running without an interval.
What if your joke doesn't land?
An occasional flat joke is inevitable. I have said things that deserved a laugh and received instead the sort of silence normally reserved for failed diplomatic negotiations.
Nothing dramatic happened. The earth continued rotating. The women involved remained free to make up their own minds about me.
If a joke fails, you can smile and move on. If you misjudge it and cause offence, apologise plainly. "Sorry, that came out badly" is much better than insisting, "It was only a joke," until she agrees to forgive you.
Don't double down. Don't explain the joke in six stages. And don't assume that one quiet reaction means she has no sense of humour. Perhaps the joke wasn't funny. It happens to the finest of us and, I regret to say, even to me.
A man who can recover from a small embarrassment gracefully is far easier company than one who treats every chuckle as a referendum on his desirability.
Find your shared ridiculousness
The most enduring humour often comes from details that belong only to two people. The bakery whose croissants look like small collapsed tents. The waiter who described sparkling water as though presenting a royal infant. Her niece's particularly fierce opinion about garden gnomes.
These aren't necessarily jokes you'd tell at a dinner party. They're funny because you experienced or discussed them together. When you refer back to one later, it quietly says you remember the moment.
Don't force a running joke to become your official couple's catchphrase after a single afternoon. If it develops, let it develop. The same principle applies to flirtatious nicknames: if she enjoys one, lovely; if she doesn't, retire it without debate.
Shared humour should make both of you feel included. That is a much better ambition than trying to score points for originality.
If you're not naturally funny, relax
Some men are rapid-fire jokers. Others are quietly observant, dry, absurd or wonderfully good at laughing. There is no single approved comic personality for heterosexual courtship.
You don't need to compete with the loudest fellow in the pub. If you find something amusing, say so. If a funny story occurs to you, tell it briefly. If she makes you laugh, enjoy that without trying to pay her back immediately with a superior joke.
It's also perfectly possible that your humour won't click with a particular woman. She might adore surreal nonsense while you prefer dry understatement. Neither of you is defective; the wavelengths simply differ.
Trying to become someone else's ideal comedian is exhausting. Better to discover whether your actual sense of humour makes the two of you happy together.
Leave the stage and enjoy the date
The final secret, if we insist on calling it one, is that a good date doesn't require constant laughter. There should be room for curiosity, attraction, stories, food, pauses and the occasional unremarkable comment about the weather.
Use humour to share delight, not to avoid being known. Notice the absurd, welcome her jokes, and allow yourself to look a little foolish without collapsing into self-consciousness. If you both laugh freely, wonderful. If the evening is warm and interesting with only the odd chuckle, that can be wonderful too.
Attraction is not measured by jokes per minute. There is no golden ratio of puns to compliments, and no certificate issued by the Guild of Romantic Comedians.
Make her feel comfortable enough to be funny herself. That's when the real entertainment begins.