To flirt with a dry sense of humour, use the understated observations and straight-faced remarks that come naturally to you, make sure she can tell you're being playful, and leave room for her to join in. Tease lightly about harmless situations, not personal insecurities. A small smile or warm follow-up can stop a deadpan joke sounding like a genuine insult. If she enjoys your humour, let it become a shared language; if she doesn't, don't insist that she ought to find it funny.
I have always admired the British ability to describe a catastrophic event as “slightly inconvenient”.
A gentleman can lose his luggage, discover his hotel has burned down and arrive at dinner wearing an emergency dressing gown, yet still remark that the holiday has “developed one or two complications”.
Dry humour is a magnificent instrument when deployed with grace.
In romantic company, however, it can be misread. Particularly when the man delivering the joke has the facial expression of somebody inspecting an exceptionally dull financial document.
I speak from experience.
At a country-house lunch I told a woman that the chef's towering seafood arrangement appeared to have been designed by an engineer who disliked gravity.
She stared at me.
“Are you complaining?” she asked.
“Not at all. I rather admire a prawn with ambitions.”
She laughed then. My first remark had been so deadpan that she'd taken it for a serious criticism.
The lesson wasn't to abandon my style. It was to remember that a new acquaintance hasn't yet learned how to interpret it.
What makes dry humour flirtatious?
Dry humour often involves saying something absurd in a calm, matter-of-fact manner.
“You seem worryingly confident about that pub quiz answer.”
Or, after she chooses the enormous chocolate pudding: “A modest selection. I admire your restraint.”
When she's smiling and the subject is harmless, a remark like that can create an amusing little exchange.
But the words alone don't do the work. The situation, your expression and her reaction determine whether it feels playful.
If she doesn't know you, “You're worryingly confident” might sound like an actual criticism. A slight smile or a follow-up that shows warmth helps establish what you mean.
The intention is to share a joke, not to test whether she can decipher your sarcasm under examination conditions.
A woman who enjoys understatement may immediately return the remark. Another may prefer direct warmth. Both responses are perfectly reasonable.
Start by making the situation the joke
If you're newly acquainted, the safest material is often something around you rather than something about her.
At a café, an impressively enormous cake arrives.
“I see they've interpreted ‘small slice’ with admirable generosity.”
At an exhibition, a sculpture seems to consist entirely of three household objects.
“I believe my shed has been producing modern art without permission.”
On a train that's stopped for the third time:
“Excellent. A scenic tour of the same platform.”
The humour arises from something you both understand. She can laugh, add an observation or simply continue chatting.
If she plays along, the exchange may become lightly flirtatious because you've created a shared amusement.
Avoid mocking service staff or other guests. You needn't turn a pleasant outing into a comprehensive review of everything you dislike.
Monty can assure you that a man determined to criticise the entire world will eventually be dining alone.
Let her see that you actually like her
Here's the danger with a relentlessly deadpan manner: she may wonder whether you're enjoying yourself.
You think you've been wonderfully funny. She thinks you've spent an hour assessing her taste in restaurants.
Add an occasional direct expression of warmth.
“I'm having a really nice time with you.”
Or after a playful exchange: “I like your sense of humour. It's rather dangerous.”
That little dose of sincerity makes the banter easier to understand.
You don't have to become sentimental or abandon your personality. Just don't conceal every positive feeling behind an ironic remark.
The woman you're hoping to date shouldn't need a professional translator to discover that you fancy her.
She needs to feel that you're pleased to be in her company.
Monty and the woman who out-dried me
I once met a woman named Clara at a vintage railway exhibition.
A volunteer proudly explained that an early carriage had possessed “surprisingly adequate” ventilation.
I observed that the passengers must have been positively overwhelmed by luxury.
Clara, without changing her expression, said, “And to think they were allowed to travel without a complimentary cheese board.”
I knew immediately that we would get along rather splendidly.
We moved on to a display of old railway timetables. She examined a notice warning passengers not to lean out of the windows.
“Thoughtful,” she said. “I was considering taking the entire journey outside.”
“An economical way of enjoying the scenery.”
For twenty minutes we conducted an increasingly ridiculous conversation while outwardly appearing to discuss railway history.
Neither of us needed to tell a conventional joke. We had discovered a rhythm in which each remark invited the next.
It was flirtatious because of the shared attention, not because the railway jokes themselves possessed magical romantic properties.
How to tease without becoming unkind
Dry humour can become sharp very quickly.
A gentle comment about a ridiculously elaborate menu may be amusing. A deadpan remark about her intelligence, body, job or family might feel cruel, even if you intended it as a joke.
Don't use sarcasm to attack something she cares deeply about, particularly when you've only just met.
Suppose she says she loves gardening.
“You're brave. I've managed to kill a cactus.”
That's self-directed, light and easy to answer.
Compare it with, “What an exceptionally boring way to spend a weekend.”
The second may sound contemptuous.
If she seems hurt, apologise briefly and sincerely. Don't announce that she obviously has no sense of humour.
A joke that requires the other person to swallow an insult isn't an achievement in wit.
Don't mistake her smile for a standing invitation
Some people laugh at awkward moments to keep conversation pleasant. Others have a naturally friendly manner.
So a returned joke or a warm smile can be encouraging, but doesn't prove she wants romance.
Pay attention to the wider exchange. Is she choosing to continue talking? Asking about you? Offering her own playful remarks? Happy when you suggest spending more time together?
If so, you may have grounds for a gentle invitation.
If she becomes quiet, looks away or stops joining the humour, return to ordinary conversation or leave her space.
Don't deliver increasingly pointed jokes in an attempt to “win her over”.
Your sense of humour can be a charming part of your personality. It can't overrule someone else's preferences.
What if she doesn't understand your joke?
Then explain lightly if it matters, or let it go.
Perhaps you say, “I see the orchestra has decided to begin playing in a different key from the singer.”
She looks alarmed. “Really? I thought they were lovely.”
You can smile and reply: “I'm being unfair. I actually enjoyed it.”
No lecture on irony required.
If she repeatedly takes your deadpan remarks literally, it may simply be a difference in humour. You can still enjoy her company if you make an effort to speak directly.
But don't demand that she adopt your style.
Compatibility includes the way two people speak, and not every combination produces effortless banter. That doesn't mean either person has failed an intelligence test.
A woman who prefers plain sincerity isn't obliged to become a student of your comedy.
Use the dry remark to open something more personal
You can combine a witty observation with genuine interest.
She tells you she recently started learning French.
“Wonderful. You can now order cheese in two languages, which seems a worthwhile investment.”
Then ask what inspired her.
If she laughs and tells you about an upcoming trip, follow her story.
Your joke was the doorway. The interesting part is finding out what she cares about.
Or perhaps you both dislike the same dreadful television programme. You can exchange a few lines and then ask what she actually enjoys watching.
Don't spend the entire evening describing the things you hate. Even the most beautifully delivered sarcasm becomes tiresome if it has no affection underneath.
Flirting is an exchange that helps two people grow curious about each other.
Deadpan compliments can be delightful
A little dry humour can make a compliment feel charming, provided the admiration is obvious.
After she's told a particularly clever story, you might say with a smile, “Well, that's inconvenient. I was hoping to be the interesting one tonight.”
Or: “You're making it extremely difficult for me to maintain my reputation as a serious gentleman.”
These suggest that you like her company without being grandiose.
But sometimes the best compliment is completely straightforward.
“You look lovely.”
“I've enjoyed spending time with you.”
Say it plainly. A moment of sincerity can feel particularly meaningful from somebody whose usual style is understated.
Don't bury everything positive beneath an ironic disguise.
There is no rule that a dry gentleman must remain sarcastic until the conclusion of the relationship.
How to use dry humour in messages
Text messages remove your expression and tone, so jokes can become easier to misunderstand.
Keep early messages clear. A playful observation about something she mentioned is usually better than an elaborate insult disguised as teasing.
She sends a photograph of a spectacularly lopsided cake.
“An architectural statement. I admire the confidence.”
If she laughs and tells you what happened, delightful. If she seems confused, clarify rather than repeating the line.
Avoid sarcasm about delayed replies, appearance or her romantic intentions. Without tone, “Nice of you to finally reply” can sound resentful rather than amusing.
You can also add an ordinary question to a joke so she has somewhere to take the conversation.
A message that makes her smile and invites a reply is much better than a cryptic sentence she must decipher.
From banter to an unmistakable invitation
Here's where dry humour needs to make room for clarity.
You and a woman have been exchanging remarks for half an hour. You like her. She seems to enjoy you too.
Don't rely on sarcastic hints until the sun burns out.
Try: “That was a superb conversation. Shall I take you for dinner on Friday and risk a second opinion?”
If you prefer, add a small flourish: “I promise to complain about the menu only if it deserves it.”
But make the invitation clear. She's entitled to accept, decline or ask for time.
Don't turn a refusal into another joke at her expense. A polite “No problem, lovely meeting you” keeps everybody's dignity intact.
A real romantic possibility begins when two people know what has been offered.
Clara's verdict on my considerable charm
At the end of the railway exhibition, I suggested a drink.
Clara considered the offer with enormous gravity.
“I'm not sure,” she said. “You appear to have a troubling fascination with train timetables.”
“A fair criticism. I promise the conversation will eventually move beyond British Rail.”
She laughed and accepted.
Would that exchange appeal to everybody? Certainly not. Some would find us both utterly insufferable. I can live with that.
But we'd discovered a way of amusing one another and made an invitation without pretending to be different people.
That is the pleasure of flirting with dry humour: noticing something ridiculous, sharing the moment and letting genuine warmth show through the understatement.
You can find my fourteen-page Babe Magnet introduction through the free-guide offer below. Even a dry old devil deserves a little romance.
And if your date says she finds your jokes a little dry, old boy, do resist the temptation to offer her a glass of water.