The most natural way to compliment someone's sense of humour is to react to a joke you genuinely enjoyed and say what made it funny. "Your timing was perfect," "That was wonderfully dry," or simply "You've made me laugh more than anybody tonight" can mean far more than a rehearsed declaration about how hilariously funny she is. Let the compliment belong to the moment, and don't make her perform another joke to earn it.
Humour is a splendid thing to find in another person. I particularly admire someone who can make an entire table laugh without raising her voice.
If she makes a remark that catches you by surprise, enjoy it. You don't have to perform a lengthy tribute to her comic genius. "That was good" and an actual laugh will often do.
And if she's funnier than you? Splendid. One less job for Monty to do over dinner.
Say what made you laugh, not just that she's funny
"You have a good sense of humour" is perfectly pleasant. The trouble is that it can sound as if you've reached the end of an evaluation form.
A specific reaction shows that you were paying attention.
She tells a story with a wonderfully slow build, then delivers an unexpected ending.
"You told that brilliantly. I never saw the last bit coming."
She makes a dry observation while everyone else is taking a minor inconvenience terribly seriously.
"I love how you can make one quiet remark and finish the whole argument."
She recalls a funny detail from an earlier conversation.
"I can't believe you remembered that. You've made it even funnier."
You aren't praising an abstract quality. You're appreciating a moment the two of you actually shared.
If nothing has amused you, don't invent a compliment. You can be interested in her without pretending she's a professional comedian.
Timing matters more than elaborate wording
The best moment to compliment a joke is often immediately after it lands.
Laugh, enjoy it and say something simple. Then move on with the conversation.
You don't need to interrupt her before she's finished, lean forward solemnly and announce that you've identified evidence of unusually strong comedic ability.
Nor should you spend five minutes dissecting her technique. Unless you're both discussing comedy as a craft, a full critical analysis can murder the joke on the examination table.
A small response may be more natural: "Oh, that's very good." A grin may do half the work.
Suppose she sees a peacock strutting across the garden and says it has "the confidence of a minor royal". If that makes you laugh, let her know. "That's exactly what he looks like" would be a perfectly natural reply.
She knew she'd landed it. There was no need to commission a plaque.
Different kinds of humour deserve different reactions
Some people are wonderfully quick. Others are storytellers. Some deliver deadpan observations that take a second to register. Others are gloriously silly.
Compliment the quality you've noticed.
For dry humour: "That was so understated I nearly missed it. Brilliant."
For a witty comeback: "You had that ready far too quickly. I'm impressed."
For a funny story: "You tell stories beautifully. I felt like I was there."
For a ridiculous impression: "That was alarmingly accurate. Should I be worried?"
For shared playful teasing: "I see I've met my match."
These are examples of ordinary speech, not lines to fire off in sequence. If you would never say "alarmingly accurate" outside a Monty article, find your own words.
And if she is nervous about whether a joke landed, don't exaggerate. An honest smile and "I enjoyed that" are reassuring enough.
Don't turn appreciation into a demand
Imagine somebody tells you you're a brilliant pianist, then asks you to play six more pieces while they eat dessert.
A compliment becomes a job offer.
The same happens when a woman makes you laugh and you immediately say, "Go on, say something else funny," or "Do that voice again, everyone needs to hear it."
She may enjoy being funny. She may not want to be your evening's entertainment.
Laugh and contribute. Give her the pleasure of hearing your own story or joking with you.
If she tells another joke of her own accord, excellent. If she wants to discuss something serious, follow the conversation.
A woman who has a great sense of humour is still allowed to spend half an hour talking about work, family or the difficulty of finding decent shoes.
Appreciate humour without making her the centre of attention
A public compliment may sound generous to you and uncomfortable to her.
At a group dinner, you might be tempted to announce, "Everyone, listen to what she just said! She's hilarious!"
Perhaps she'll love the attention. Perhaps she'd rather keep the private joke between the two of you.
Notice her comfort with the group. If she's reserved, a quiet "That was excellent" may be more welcome.
Don't repeat her joke without credit, and don't use it to make yourself the star. If she would rather not tell an embarrassing story to a roomful of strangers, don't insist that she share it because you found it funny.
The purpose is to appreciate her humour, not recruit an audience.
For more about the pleasure of quieter jokes, see flirting with a woman who prefers subtle humour.
Can a sense-of-humour compliment sound flirty?
Absolutely, especially when it's part of an enjoyable romantic exchange.
"I like being around you. You make even a dull evening entertaining."
"I was looking forward to this, but I didn't expect to laugh quite so much."
"You've got a wonderfully wicked sense of humour. I rather approve."
These can express attraction if they're genuine and appropriate to the relationship.
But don't confuse laughter with a guarantee of romantic interest. She may enjoy your company and not want to date you. The way to find out isn't to analyse how many times she laughed.
If you'd like to see her again, say so. "I've had such a good time talking with you. Would you fancy dinner next week?"
The compliment provides warmth. The invitation provides clarity.
How to compliment her humour over text
Text is particularly good for referring back to a shared joke, provided you don't beat it into the ground.
She made a remark about your disastrous attempt at cooking. The next day you message:
"I made toast successfully this morning. Your confidence in my culinary future was clearly misplaced."
That's a callback and a little self-mockery.
If you want to compliment her directly, you could say, "That message about my kitchen has been making me laugh all morning."
The point is that you name the actual moment.
Avoid sending "You're so funny" to every message. Praise loses meaning when it arrives on a schedule.
And don't interpret a delayed reply as permission to send several increasingly elaborate attempts at comedy. She might simply be busy.
If the exchange is running well, you can suggest meeting rather than keeping every bit of your interest trapped inside a phone.
Compliment the joke without endorsing something unkind
What if she makes a joke at somebody else's expense and you don't like it?
You aren't obliged to laugh just because you're attracted to her.
You can stay neutral, change the subject or disagree calmly if it's important.
"That's not quite my sort of humour," said without a lecture, may be enough.
Don't reward a cruel remark to demonstrate that you're relaxed and easygoing. That tells her very little about your actual values.
Equally, humour can be misunderstood. A joke may depend on context you don't have. Ask what she meant if you'd like to understand, rather than declaring her a terrible person from one sentence.
Mutual attraction shouldn't require either of you to abandon your judgment.
What if you're naturally serious and she's wonderfully funny?
You don't need to match every joke with one of your own.
Laugh when you're amused. Listen closely. Offer a thoughtful response.
A calm man can enjoy being with a quick-witted woman without competing for the most laughs. You can compliment her timing and then tell a completely ordinary story about your week.
Trying to outdo her may make you miss the best parts. If she says something brilliant, let it stand instead of topping it with a five-minute anecdote.
Of course, if your senses of humour are radically different, notice that too. It's useful information about compatibility. You might enjoy each other enormously—or find it tiring.
Neither of you is required to perform a personality transplant.
The Monty Files guide to building rapport while flirting deals with finding an enjoyable conversational rhythm even when your styles aren't identical.
What if she doesn't accept the compliment?
Some people say, "Oh, that wasn't funny," even after they've made the room laugh.
You can smile and say, "Well, I thought it was."
Then leave it. You don't need to argue that she's objectively hilarious.
If she seems uncomfortable with being praised publicly, keep future compliments discreet. If she changes the subject, follow it.
A compliment is something freely offered, not a verdict the recipient must accept.
Avoid adding a demand for a compliment back. "Surely you think I'm funny too?" drains the ease from the moment.
Your job isn't to obtain a glowing review of your own wit.
Complimenting someone you know well
As you get to know someone, humour can become one of the things that makes the relationship special.
You may have a running joke that nobody else understands. You know which silly programme will make her laugh after a long day. She knows precisely which of your ridiculous poses will embarrass you in a photograph.
A lovely compliment can refer to the effect her humour has on your life.
"You always know how to make a grim day better."
"I love that we can laugh about the tiniest things."
"I'd forgotten how much fun ordinary errands can be with you."
These carry more weight after a history together than when delivered to someone you've met twice. Don't borrow the emotional language of a long relationship before you've built one.
And keep appreciating other parts of the person too. Nobody wants to be reduced to "the funny one" forever.
Praise a funny observation, then continue the conversation
Imagine you've been to the theatre together and she makes a wonderfully dry remark about an actor whose cloak has taken on a life of its own.
Laugh if it's funny. "That was excellent," is a perfectly good compliment. Then talk about the play. What did she enjoy? Did you agree about the ending? Is there something you'd both like to see next?
You don't need to keep returning to the cloak, or beg her to invent another joke. She's a person you want to know, not an entertainer hired for the interval.
If you've had a lovely evening and want another, say so. "I've really enjoyed your company. Would you like to go out again next week?" makes your interest clear, with no joke required.
The best compliment is a specific, warm response to something you truly enjoyed. The rest is simply having a conversation in which both people get a turn.
For more of Monty's practical dating advice, the free 7 Secrets to Becoming a Babe Magnet is yours for the asking.