The best compliments are sincere, specific and comfortably timed. Notice something she chose, did or said—her sense of humour, an interesting opinion or an outfit that suits her—without piling on extravagant praise. A simple 'I really enjoy talking with you' often says more than a rehearsed speech.
Somewhere in Britain, at this very moment, a man is preparing to compliment a woman by telling her that her eyes look like two shimmering oceans and that her smile could light up the entire planet.
He's met her twice. They are standing beside the self-service tills in Tesco.
There is a time and place for extravagant romantic language. There are also moments when a simple "You look lovely" achieves considerably more than comparing somebody's facial features to the North Atlantic shipping lanes.
Compliments ought to be one of the easiest pleasures of flirting. You notice something genuinely appealing about another person, and you let them know. Yet some men turn the business into a nerve-racking exercise, terrified of coming across too keen or, at the opposite extreme, firing out flattery with the subtlety of a man distributing discount vouchers outside a shopping centre.
The trick is not finding the perfect line. It's learning to notice, mean and deliver something kind without making the recipient responsible for rewarding you.
Start with something you actually believe
I'm going to save you the trouble of memorising fifty elaborate compliments. The words matter less than the sincerity behind them.
If she has a beautiful smile, you can say so. If she has chosen a striking coat, mention that. If she has just told a brilliantly funny story, tell her she made you laugh. It isn't a competition to invent the most extraordinary description of an ordinary human characteristic.
A woman can usually tell when the compliment belongs to the situation and when it has been carried around in your pocket waiting for the next available recipient.
"That's a fantastic colour on you" might be genuine. "You possess the most exquisite aura I've encountered in my travels" may be a stretch, unless you are a retired Victorian spiritualist. Even then, perhaps proceed carefully.
You don't need to compliment everything. One well-placed remark, delivered naturally, often carries more warmth than an entire evening of continuous praise.
Notice choices as well as appearances
Appearance compliments can be welcome in a romantic setting, but they're hardly the only kind worth giving. Some of the most memorable ones recognise things a woman has chosen, created or expressed.
Maybe she has a wonderful dry sense of humour. Perhaps she's extraordinarily knowledgeable about architecture, speaks passionately about her work or has found a clever way to solve a difficult problem. Maybe she has turned up in an outfit that is unmistakably her own.
"I like the way you think about that" is a compliment. So is, "You've got a wicked sense of humour," when she actually does. "That jacket is magnificent" notices her style rather than conducting an appraisal of her body.
These remarks can feel personal because they show you've been listening and looking at the person in front of you, not merely scanning her for conventional beauty markers.
Mind you, don't swing so far the other way that you refuse to mention attraction altogether. If you're on a date and think she's gorgeous, saying "You look gorgeous" isn't some dreadful social crime. Context and delivery are what make the difference.
Compliment her without assessing her
There's a distinction between appreciating someone and issuing a judgement as though you're chairing a panel of judges.
"You look beautiful in that dress" is a compliment. "That dress makes you look much slimmer" introduces an assessment she never requested. "I love your laugh" is warm. "You'd be prettier if you smiled more" is criticism masquerading as encouragement.
Avoid comments that depend on comparing her with other women. "You're not like most girls" might be intended as flattering, but it asks her to feel special because you've insulted a large section of the population. "You're actually clever as well as pretty" is worse, implying you expected beauty and intelligence to arrive in separate parcels.
Similarly, don't disguise your own preferences as advice. You're not there to provide unsolicited improvements to her hairstyle, clothes or body. Even a beautifully tailored opinion can still be an opinion nobody asked for.
If a compliment needs someone else to be put down, or makes her wonder what you found wrong with her last week, it probably needs retiring.
The first-date compliment: keep it easy
A first date is a good moment for a simple, warm remark. When she arrives, "You look lovely" followed by a smile is perfectly sufficient. Then let the evening begin.
Some men get caught in a peculiar trap here. They announce she looks beautiful, wait for a particular response, don't receive it, and decide the compliment has failed. So they try another. Then another. Before long, the poor woman is being praised at ten-minute intervals like a prize-winning rosebush.
A compliment is a gift, not a request for applause. She may smile, thank you, return one or simply move the conversation along. All are acceptable reactions.
If she seems uncomfortable with remarks about appearance, change course. You can still be friendly and interested without returning to the same subject. People have different histories and preferences, and the safest way to learn them is by paying attention.
If you feel nerves rising before the first compliment, don't make a ceremony of it. Just say the ordinary words in your ordinary voice. Then ask about her day, get the drinks or continue the conversation.
Can you compliment her body?
Sometimes, in an established flirtatious relationship, more intimate compliments are entirely welcome. The important words there are established and welcome.
On a first meeting, a running commentary about her body is usually a poor opening move. It can make her feel observed rather than known, particularly if she's simply going about her day and hasn't indicated any romantic interest.
On a date where attraction is clear and mutual, a tasteful remark may fit naturally. But don't assume that because she's dressed attractively, she has asked for explicit comments. Clothing isn't a permission slip.
And don't confuse boldness with being sexually graphic. It's possible to communicate attraction through an appreciative smile, a warm compliment or an openly flirtatious exchange without delivering the sort of remarks that would cause a seaside postcard to blush.
If you're wondering whether a particular line might make her uncomfortable, ask yourself whether you'd be content to say it in a calm conversational tone, then give her full freedom not to engage. If the remark depends on shock value or pressure, leave it unsaid.
What about complimenting someone you don't know?
Here context matters even more. A woman waiting alone at a bus stop, working behind a counter or wearing headphones on a train isn't necessarily inviting an interaction simply because you find her attractive.
A brief, respectful compliment on something non-intimate may sometimes be fine, particularly in a social setting where conversation is already happening. But a stranger doesn't owe you her attention, her smile, her number or even a reply.
Don't trap someone in a doorway, follow her after she walks away or keep talking once her lack of interest is clear. A compliment isn't charming if its recipient has to plan an escape route.
It can help to direct the remark towards an obvious choice rather than her body: a striking pair of earrings, a wonderful hat, the novel she's discussing at a book event. Even then, the circumstances must allow her to disengage comfortably.
If what you actually want is to strike up a conversation, be straightforward about that rather than using flattery as a way around her boundaries.
Don't hide an insult inside a compliment
I know there are people who advise men to use so-called backhanded compliments: offer a little praise, smuggle in a small criticism and supposedly make the woman eager to win your approval.
You could also establish romantic chemistry by tipping a drink over your own trousers and claiming it's an advanced social technique. Both approaches have approximately equal dignity.
"You look good for your age" suggests you're surprised she's still presentable. "You're prettier without all that make-up" insults her choices. "I usually go for taller women, but you're cute" is not a compliment; it's a small personal inconvenience dressed as flirtation.
Teasing can absolutely be fun between people who know one another and share a similar humour. But teasing works because both people are enjoying it. If one person is left feeling judged, it has ceased to be charming.
Don't try to generate attraction by making someone less secure. You've got more interesting things to offer than that.
A compliment shouldn't be a bargaining chip
Picture the scene. You say she has a wonderful smile. She says thank you. You then decide she must like you, agree to a drink and furnish the details of her weekend because you've spent the required social currency.
No, old chap. That's not how any of this works.
If you praise someone because you'd like them to feel good, the compliment has succeeded as soon as you've said it sincerely. It doesn't purchase a conversation, a date or physical affection.
The same applies once you're seeing each other. Don't turn kindness into a running ledger: seven compliments, two restaurant bills, one bouquet, therefore an entitlement to intimacy. Romance wilts rather quickly under accountancy.
Flirting contains an element of risk. Sometimes your admiration is returned; sometimes it isn't. The ability to accept either outcome without resentment is part of what makes you pleasant company.
Learn the pleasure of being specific
The best compliments often reveal something you've genuinely noticed. Instead of calling her "amazing" for the eleventh time, mention the particular thing that caught your attention.
"I loved how you dealt with that awkward situation — you made everyone feel at ease" tells her you saw her kindness and judgement in action. "You have a talent for making ordinary stories hilarious" is more vivid than "You're funny." "That blue really suits you" feels more immediate than a grand declaration about beauty.
Specificity needn't mean producing a paragraph. In fact, a concise remark often lands more comfortably because it doesn't demand a grand reaction.
The art of accepting a compliment yourself
A gentleman who wishes to give compliments gracefully should also learn how to receive them without staging a public dispute.
If she says your shirt looks good, you needn't reply, "This old thing? I found it behind a radiator. I look like a bus conductor." A simple "Thank you, that's lovely of you" will do.
You needn't immediately return a compliment, either. Forced reciprocity can feel rather mechanical. If she praises your eyes and you instantly praise hers with identical enthusiasm, the exchange starts resembling two estate agents congratulating each other on a successful viewing.
Accept warmth when it's offered. Enjoy it. Respond naturally. Being at ease with positive attention is a quiet but rather appealing sort of confidence.
What to say when words don't quite arrive
Sometimes you meet someone and genuinely think she looks wonderful. Your brain, normally a reasonably reliable piece of equipment, promptly refuses to supply a single adjective. Don't panic.
You can say, "You look lovely tonight." You can say, "I really like that dress." You can say, after she's made a sharp observation, "I like your sense of humour."
There is no emergency requirement to improve upon the language of Shakespeare. A genuine compliment isn't diminished by being straightforward.
The most attractive quality isn't verbal fireworks; it's the feeling that your remark is intended for this particular woman at this particular moment. And after you've said it, you're perfectly content for her to carry on being herself.
That, to my mind, is the whole trick. Notice something lovely, say something true, and don't stand there waiting for a medal.