If you're not naturally funny, flirt by being genuinely interested, offering a thoughtful compliment, sharing your own opinions and making a clear invitation when the conversation feels mutual. You don't need jokes or lightning-fast banter to create attraction. Warmth, attention and a little honest playfulness can show a woman that you enjoy her company. Don't force humour that doesn't sound like you; build the conversation around what you actually notice and feel.
There exists a peculiarly cruel myth that every successful romantic encounter must be conducted by a man with the timing of a professional comedian.
By this theory, a woman approaches, you produce a devastatingly clever line, she collapses into helpless laughter and a relationship materialises before the pudding.
It's an impressive piece of fantasy.
I have known magnificently funny men who made dreadful dates because they could never stop performing. I've also known quiet, thoughtful fellows whose romantic appeal lay in being warm, interesting and utterly sincere.
One such man was Edwin, a successful furniture maker and perhaps the least naturally amusing person I've ever taken to lunch.
He told jokes in a voice normally reserved for reading out insurance exclusions. If somebody said something funny, he would laugh approximately six seconds after everyone else, often while carefully putting down his fork.
And yet women regularly enjoyed his company.
“What's your secret?” I asked him.
He looked perplexed.
“I ask them about themselves,” he said.
I nearly wrote the answer on a silver plaque.
Stop trying to be the funniest man she has ever met
A date isn't a comedy audition. If you spend your entire evening hunting for the next joke, you'll miss the woman sitting opposite you.
Perhaps she mentions an unusual holiday or a hobby she's taken up. Listen properly. Ask what she enjoyed, what surprised her or how she first became interested.
An honest, interesting question can be more engaging than a clever remark that's only loosely connected to what she said.
“You mentioned you're restoring a little sailing boat. What made you take that on?”
That shows attention. It also gives her room to speak about something she cares about.
When she answers, share a thought or experience of your own. You might admire the project or confess that your most ambitious repair was a cupboard door.
No punchline required.
You're not competing with the comedian at the next table. You're trying to discover whether you like one another.
The attraction in being quietly interested
Edwin could make another person feel thoroughly heard.
At a gallery supper, he met a woman named Rosalind who designed theatre costumes. Most of the men at the table tried to impress her with opinions about the production.
Edwin asked how she made a dress survive eight performances a week.
She explained a remarkable system of hidden fastenings and reinforced seams. He was fascinated. Furniture and costume design, it turned out, shared several surprising problems: fit, wear, weight and the need for something to look effortless despite hours of difficult craftsmanship.
They spoke for nearly an hour.
Not once did Edwin produce what a dating coach would call a “killer line”. He simply noticed that her work interested him.
That attention became flirtatious when he allowed it to be personal: “I like the way you talk about your work. You make me notice details I'd normally miss.”
It was unmistakably warm. It was also true.
There is considerable charm in a man who doesn't feel compelled to turn every sentence into entertainment.
Use small compliments rather than grand speeches
A useful compliment needn't be funny.
“That's a lovely colour on you.”
“You've got such an enthusiastic way of telling stories.”
“I've been looking forward to seeing you again.”
You can say these things in your normal voice. There's no need for an exaggerated pause or a flourish at the end.
Choose something that's actually appropriate to how well you know her.
A compliment about her humour, kindness or taste can be delightful. A stranger's highly personal assessment of her body is another matter entirely.
And don't repeat praise until she produces the reaction you were hoping for. Give it freely and let the conversation continue.
If she seems happy with the attention, fine. If she looks uncomfortable or changes the subject, take the hint.
Attraction cannot be bought in units of flattery, however beautifully packaged the compliments may be.
Have a point of view that belongs to you
Some men worry that without jokes they won't have anything interesting to say.
But your tastes and opinions are material too.
What do you love doing when nobody is watching? Which place would you revisit tomorrow? What is the most ridiculous thing about your job? What have you changed your mind about recently?
You don't need to prepare speeches. You simply need to give a little more than one-word answers.
“I like cooking,” says Edwin.
“What do you make?” asks Rosalind.
“Furniture,” he replies, quite seriously.
There was an awkward pause.
Then he added, “Food-wise, I'm learning to make a proper risotto. The first attempt could have repaired a loose table leg.”
That line wasn't part of a routine. It came from the real frustration of a man who understood adhesives rather better than rice.
Even if Rosalind hadn't laughed, she could still ask what happened.
A naturally interesting detail gives another person somewhere to go. It's worth far more than a recycled internet joke.
Playfulness isn't identical to telling jokes
You might not be the sort of man who can invent a punchline. You may still enjoy a little playful disagreement.
She says she thinks pineapple belongs on pizza.
You might reply, “I'm unconvinced, but I'll allow you to present your case.”
She laughs and begins explaining. You pretend to consider the evidence. The conversation becomes lightly flirtatious because you're sharing a game.
But there's no obligation to argue. If you're quieter, perhaps your playfulness is a smile and a dry observation.
“You seem rather pleased with that outrageous opinion.”
If she enjoys it, carry on. If she doesn't, stop teasing and return to ordinary conversation.
Good playfulness has room for both people. It's not a script you inflict upon a woman until she appreciates your technique.
A gentleman can have a serious manner and still be delightful company.
What if she has a much stronger sense of humour?
Excellent. You may have an entertaining evening.
Don't assume you must compete with her wit or prove that you can match every joke.
If she tells a funny story, laugh because you find it funny. Ask what happened next. Offer an observation of your own if one occurs naturally.
You can even admit that she's quicker with a joke.
“I suspect you've got all the best lines tonight. I shall have to contribute the refreshments.”
That can be charming if you mean it lightly, not as an invitation for her to rescue your self-esteem.
It's also possible that she likes somebody who listens without constantly interrupting her to deliver a more elaborate punchline.
Or she may prefer a more boisterous companion. That's her decision, not an instruction for you to manufacture a new personality.
The purpose of a date is to find somebody whose company suits yours.
Don't be the man who quotes other people's jokes
Edwin once attempted to memorise a series of amusing chat-up lines from a website.
He practised them aloud while polishing a mahogany cabinet.
One involved a library card. Another mentioned a parking fine. A third required the woman to answer a question about astronomy before he could deliver the punchline.
By the time we went to dinner, he was so worried about remembering them that he barely listened to anybody.
“Edwin,” I told him, “if you're going to become somebody else, at least choose a man with better material.”
He abandoned the collection.
Instead he told Rosalind about a disastrous restoration commission involving a piano stool and a very demanding dachshund.
The story was funny because it was specific, true to him and utterly unexpected. He hadn't sat down with the intention of being amusing.
This is the difference between sharing a ridiculous experience and performing a joke. One is part of your life. The other may belong to somebody you've never met.
How to show romantic interest without a punchline
Here's the part that really matters.
You can be thoughtful, serious and engaging, but if you never show personal interest, she may reasonably believe you're simply being friendly.
A warm comment can change that.
“I really like spending time with you.”
“I'm enjoying getting to know you.”
“You have a lovely way of looking at things.”
None is a joke. Each can be romantic when the setting and connection are right.
Then, if the two of you seem to be enjoying one another, offer an actual date.
“I'd love to take you to that exhibition you mentioned. Are you free next Saturday?”
You're not promising to sweep her off her feet. You're giving her a clear, comfortable opportunity to say yes or no.
And that's a perfectly decent beginning to romance.
Silence doesn't require an emergency joke
There will be a pause. Perhaps a waiter arrives, or you're both looking at a painting, or she's thinking about what to say.
Don't fill it with the first funny thing that comes to mind.
A moment of quiet can be pleasant if you're both comfortable.
You might comment on the view, return to something she mentioned or simply take a drink and allow the next thought to emerge.
When you do speak, let it be connected to the moment rather than a desperate attempt to prove that your personality is still working.
I have endured a gentleman interrupting a perfectly lovely sunset to deliver a rehearsed pun about cloud formations. The pun was appalling. The silence had been much nicer.
If a woman is enjoying the conversation, you don't need to rescue it every seven seconds.
And if she isn't enjoying it, another joke won't necessarily change her mind.
Avoid self-deprecating humour that turns into an apology
You may be tempted to announce, “I'm rubbish at flirting,” before every compliment.
Occasionally an honest admission can be sweet. Repeating it creates pressure for her to reassure you.
Don't make your own supposed inadequacy the main topic.
Instead of, “I know this is awkward and you probably don't find me funny,” try saying what you actually mean.
“I like talking to you.”
Then let her respond.
A gentle joke about a genuine mishap can be charming. A prolonged campaign of putting yourself down is considerably less enjoyable.
You don't need to act as though you're the most impressive man alive. Simply allow yourself to have some attractive qualities without apologising for them.
Confidence can be quiet, particularly when it doesn't demand a witness.
Edwin's most successful romantic line
At the end of the costume exhibition, Rosalind told Edwin she'd enjoyed their afternoon.
He considered several possible amusing responses. None arrived.
So he said, “I'd really like to see you again.”
She smiled.
“I'd like that too.”
He later asked me whether he ought to have said something funnier.
“Absolutely not,” I told him. “You managed to express a real thought without comparing her to a parking ticket. This is splendid progress.”
That doesn't mean sincerity guarantees attraction. But it gives the person you're interested in a chance to meet the man you actually are.
You may be naturally hilarious, quietly dry, thoughtful or hopeless at telling jokes. Romance is not restricted to one category of personality.
Flirt with warmth. Listen. Find common pleasures. Say when you like somebody. Then let her decide whether she'd like to know you better.
If you want to work on your first impressions, my free little Monty booklet is called 7 Secrets to Becoming a Babe Magnet, and the invitation is available on this page.
Now, old boy, put down the library-card joke. The woman is talking about something rather interesting.