To feel comfortable giving compliments when you fancy someone, notice one thing you genuinely admire, say it simply, and let the compliment stand without asking for anything in return. Start with her style, humour, choices or something she's said; make comments about appearance only when they suit the familiarity and setting. You don't need a perfect line. “You have a wonderfully mischievous laugh” can be far more charming than a speech about her beauty that lasts longer than the main course.
I adore a good compliment. It is one of life's smaller luxuries, rather like a properly made martini or a silk pocket square. But a gentleman must learn to give one without turning the occasion into a public unveiling.
Consider a man called Hugo at a garden party. A woman he fancies has arrived wearing a remarkable scarlet jacket. Hugo thinks she looks magnificent.
He begins, “I hope you don't think this is strange, and obviously I'm not trying to be forward, but I wanted to mention—”
She has time to inspect the roses, refill her drink and make an entirely new acquaintance before Hugo reaches the word jacket.
The compliment was quite good. The elaborate ceremony surrounding it was the trouble.
Notice something real before opening your mouth
A compliment is most delightful when it shows you've paid attention to the individual person.
She tells a wickedly funny story about a disastrous cooking class. You might say, “You have a brilliant way of telling a story.”
She chooses a wonderful coat. “That's a fantastic coat. It really suits you.”
She describes building a little garden from scratch. “I love how enthusiastic you get about that. It sounds wonderful.”
These comments work because they refer to something she chose, did or revealed in front of you.
Compare them with a line that could be delivered identically to the next twelve women in the room. “You're the most incredible woman on Earth” isn't necessarily offensive, but after four minutes of acquaintance it's spectacularly uninformative.
You haven't learned enough about her to know that. And she has no reason to believe you mean it.
Begin with what you actually noticed. The observation itself gives the compliment personality.
Ah. Now we reach the interesting part.
You fancy her. Your compliment may reveal a little of that attraction. This is not inherently a disaster; it may be exactly what you want to communicate.
The important thing is to offer it in a situation where conversation is welcome and not demand a romantic response.
At a friend's sociable party, “I really like your style” may be a natural opening. At a date you've both agreed to, “You look lovely tonight” may be warm and appropriate.
A stranger wearing headphones in a deserted car park is not waiting for an unsolicited appraisal, however poetically phrased. A woman serving you at work is doing her job, and you shouldn't turn a routine transaction into pressure for romance.
Timing is part of charm.
If you're uncertain, begin by enjoying the conversation. A genuine compliment about something she's said often feels more natural than opening with an assessment of her appearance.
And if you do reveal interest, you can let her decide what she thinks. You needn't apologise for a respectful sentence offered at a suitable moment.
The compliment that fits into a conversation
Hugo eventually stops preparing his announcement and asks the woman whether she's enjoying the garden party.
She says she's pleased the rain has stopped because the host has spent weeks training roses around the archway. They talk about gardening, then her scarlet jacket catches the evening light.
“That jacket's magnificent, by the way.”
She smiles. “Thank you. I nearly didn't wear it.”
Now the two of them can laugh about how much effort goes into deciding what to wear. Or she may return to the roses. Either is fine.
Notice that the compliment hasn't demanded the entire conversation stop in its honour.
There was no solemn introduction, no declaration that she'd changed Hugo's life, and no request for her to compliment his clothes in return.
A compliment can be an appealing little detail in a conversation, not the subject of the whole meeting.
This is particularly useful when you're naturally shy about revealing attraction. Keep the sentence small enough to say in your normal voice.
Appearance, personality and achievement are different things
A woman may appreciate being told she looks lovely. She may also appreciate being noticed for something entirely beyond her appearance.
These aren't competing categories. They're different opportunities to show that you're actually getting to know her.
If she's told you about completing a painting, admire the work rather than pretending you've examined every brushstroke in professional detail. “The colours are wonderful. You must be pleased with how it came out.”
If she has a playful sense of humour, say what made you laugh. “That story about your brother nearly finished me.”
If she's wearing a colour you love, tell her. “That green looks terrific on you.”
Don't select a personal compliment because you read that commenting on personality is always more attractive. The point is to be truthful about what caught your attention.
A person can usually tell when you're admiring something you genuinely like and when you're handing out praise from a prepared menu.
And no, Monty has not patented the compliment about a scarlet jacket, despite considerable temptation.
What about body-related compliments?
Early in an acquaintance, intimate remarks about a woman's body can feel intrusive or sexual in a way she hasn't invited.
There's a difference between saying “You look lovely” on a mutually anticipated date and giving a detailed commentary about her figure while she's trying to choose a sandwich.
As your relationship develops, you may both enjoy more intimate praise. That becomes something you learn together, through conversation, comfort and mutual interest.
Don't assume that what pleased a former partner will please the woman you're now seeing.
If she clearly doesn't welcome a particular kind of comment, don't repeat it. You can say, “Of course,” and move on without a grand discussion about your intentions.
The aim isn't to become frightened of showing attraction. It's to let admiration develop at a pace that both people enjoy.
A gentleman who can admire a woman without treating her as an exhibit is already making an excellent start.
Here is a sentence that begins promisingly and ends rather badly:
“You have such beautiful eyes. Could you give me your number?”
The compliment has become a little piece of currency offered in exchange for contact details.
There's nothing wrong with asking a woman out when the conversation is mutually enjoyable. Just let the two things remain honest.
“I've really enjoyed meeting you. Would you fancy getting a coffee sometime?” is a straightforward invitation.
And “You have beautiful eyes” can be a compliment if the familiarity is right. It doesn't need a demand attached.
Similarly, avoid trying to extract reassurance. “I think you're gorgeous. Do you think I'm attractive too?” may put her on the spot before she's decided what she feels.
Let her compliment you when she wishes. Attraction is most pleasurable when it can travel in either direction freely.
One good remark should never become the entrance fee for a response.
If she doesn't react the way you hoped
You compliment her scarf. She says, “Thanks,” and goes back to her conversation.
That doesn't mean you've committed a disaster. It also doesn't mean she's secretly interested and waiting for you to try harder.
Accept the response and continue naturally if conversation remains welcome. Otherwise, leave her to her evening.
A warm compliment can land quietly. Some people are reserved, some are distracted, and some simply aren't looking to flirt.
If she smiles, asks about you and carries on chatting, enjoy that. If she's busy or uninterested, the appropriate next move is to respect the signal.
Don't repeat the compliment louder, add three more or ask why she didn't react.
The pleasure of giving admiration is that it can be offered freely. Once you've given it, it belongs to the other person to receive as she wishes.
That, my dear fellow, is a much better arrangement than turning a charming remark into a debt collection exercise.
When you've been dating a while
Compliments don't belong solely to the first meeting. In fact, the ones offered after you've got to know someone can become especially personal.
Perhaps she remembers that you were worried about an important family occasion and later asks how it went.
“I love that you remembered. That was really thoughtful.”
Perhaps you've watched her spend weeks preparing for an exhibition. “You've worked hard on this. I admire the care you put into it.”
Or she comes downstairs looking particularly lovely, and you simply tell her so.
No special occasion is necessary. Nor should praise be reserved for the moments when you want something.
A good relationship creates opportunities to notice details you couldn't have known on the first date: the way she laughs at terrible jokes, comforts a worried friend or becomes animated in a second-hand bookshop.
That depth is a gift of getting to know her. You needn't exaggerate it. Notice what genuinely moves you.
The danger of rehearsing compliments
Some men prepare a collection of lines before a date.
“You light up the room.”
“Your smile is a masterpiece.”
“Your eyes are like—”
At this point I advise putting down the notebook, unless you happen to be auditioning as an eighteenth-century poet.
Rehearsing a complete exchange can make you less attentive to the woman actually arriving. Perhaps she's wearing an outfit you didn't expect. Perhaps her most appealing quality turns out to be the way she makes fun of the restaurant's baffling menu.
Listen first. Let the compliment emerge from something real.
If you do find an appropriate line and stumble over it, smile. “What I meant to say is that you have a terrific laugh.” That's quite enough.
Do not attempt to rescue an awkward compliment by adding another six.
You're trying to make her feel seen, not win an award for decorative language.
If you're stuck, try mentally completing this sentence: I liked the way you…
“I liked the way you made everybody laugh when the lights went out.”
“I liked the way you described that little town. Now I want to visit.”
“I liked the way you defended that terrible film.”
You may not use those exact words, but they draw your attention towards something authentic.
They also give her a choice of how to respond. She might tell you more about the experience, smile or tease you in return.
You don't need to grade her reply. Perhaps the woman you've complimented turns out to be wonderful company. Perhaps the connection remains friendly.
A compliment isn't a machine that produces dates. It's a warm piece of ordinary human courtship, made more appealing by genuine interest.
Say it when it belongs. Then carry on enjoying the woman rather than inspecting whether you've performed it correctly.
Hugo finally notices the roses
As the party winds down, Hugo and the woman in scarlet find themselves beside the rose archway again.
“You know,” he says, “you made that dreadful weather sound almost romantic.”
She laughs. “That's because you weren't the one rescuing the tablecloths.”
He tells her he'd like to see her again, and she says she'd enjoy it too.
Perhaps they date. Perhaps they discover that their shared taste begins and ends with roses and colourful jackets. Their pleasant conversation is real either way.
Hugo has learned that you don't need the combined authority of Shakespeare and a royal herald to give a woman a nice compliment.
Notice something lovely. Say it plainly. Allow it to make a small moment warmer.
And if she happens to wear a scarlet jacket, for heaven's sake let the poor woman reach the buffet before you write a sonnet about it.