How to compliment a woman: the ‘dos’ and ‘don’ts’

Compliments are lovely. We all wish we were paid more compliments. They make the giver feel blissfully benevolent, and they make the recipient feel warm, fuzzy and engulfed in a hazy, complimentary glow. Or do they?

Truth be told, compliments are complicated. They can be great, but there’s a lot to bear in mind. ‘How to compliment a woman’ is a question we’re often asked. And so, we’re inviting you to join us on a deep dive into the world of compliment etiquette, and the various ‘dos’ and ‘don’ts’ that you need to bear in mind in social situations…

“You’re so beautiful” is far too overused, gents. Even if meant well (which it usually is), phrases like, “You’re so pretty”, or “I love your hair”, or “I’m so attracted to you” may well stem from a good, well-meaning place: but if they’re your opening move, they primarily suggest that the most important thing this particular woman can bring to the table is her looks.

We’re sure (or, at least, we hope) you don’t need us to tell you that this simply isn’t the case. If you’re on a date with a woman and you’d like to pay her a compliment, that’s a delightful urge to have. But don’t go straight for the looks. Has she mentioned what she does for a living? If her career choice is a path you admire, why not lead with that instead?

Similarly, if you’ve just met a woman on a night out, we’d strongly advise steering clear of boldly declaring your appreciation for her physical appearance. It’s invasive, and — if we’re being honest — it’s lazy, too. Engage her in conversation, learn a little about her and who she is, and compliment her on her achievements or lifestyle choices instead.

This isn’t to say, of course, that you should never compliment a woman on her looks. If you’re in a happy relationship and think your girlfriend is the most beautiful woman on earth, we have no doubt she’d be more than happy to hear your thoughts on that. But we advise steering clear of appearance-oriented compliments as a conversation starter.

The ‘empty compliment’ belongs to the realm of limp, bedraggled etiquette non-starters; and in that realm it should firmly stay. As etiquette goes, there are few things worse than a compliment paid just for the sake of paying a compliment. If you’re keen to compliment a woman, we’d advise steering well clear of tired clichés and perfunctory, performative statements (‘Nice shoes!’? Really?) : and whatever you do, don’t stubbornly insist on delivering a compliment at all costs.

Compliments shouldn’t be throwaway, or a ‘tick box’ exercise. They should be heartfelt, and they should have substance and backbone. If you want to compliment a woman but can’t think of anything to compliment her about, then we’d suggest — well, firstly we’d suggest trying a little harder, because she most likely has a great many wonderful qualities. But if you really aren’t feeling it, then abandon the exercise. Don’t scramble around for a hastily produced compliment that you don’t mean. Keep it real, and keep it honest. A fake compliment is far worse than no compliment at all.

There is no such thing as a ‘one size fits all’ compliment. If you would like to offer a woman a compliment, it’s best to focus on her, and her alone, rather than delving into the back catalogue of stored-up compliments you’ve got to hand. Remember the unfortunate Mr Collins in Pride & Prejudice? He wrote down general ‘compliments’ in a notebook that he could whip out at a moment’s notice in the future, whenever the occasion called for it. But there’s a reason this strategy didn’t serve him particularly well; it’s deeply offensive, and treats women as interchangeable and indistinguishable from each other. Don’t be like Mr Collins.

Instead, this goes back to the first “do”: learn about the woman you wish to compliment. The compliment doesn’t start with you; it starts with her. The woman you wish to compliment may not fit your idea of what a compliment should be. That’s ok. Appreciate the opportunity to learn, and to adjust your views accordingly. Dispose of your previous ‘compliment’ oriented ideas, and pay the object of your affection a compliment that speaks directly to her, and to who she is.

This is the big one, really. You may wish to pay a woman a compliment; but she may not wish to hear it. That’s her prerogative, and that’s the way it should be.

Most gentlemen have the very best of intentions when it comes to paying compliments. Good intentions are important, and we have a lot of time for them. But remember, gents; it’s not about the intention, but the impact. Your compliment may be thoughtful, kind and stemming from an honourable place; but for all that, it still may not make a woman feel good. It might not be something she wants to hear. It might make her feel pressured, or intimidated — even scared.

None of this is to imply that you meant to induce pressure, or intimidation, or fear. Most gentlemen mean the total opposite. After all, compliments are supposed to make people feel good — right? But that’s the point: if your compliment doesn’t make her feel good, then it wasn’t a compliment; and it’s important to respect that, no matter what you originally intended. You never know what she may have experienced in the past, or how she’s feeling on that particular day. Pay attention to her response; and if there’s any indication at all that she’s not feeling your compliment, then it’s time to step back.

Looking for more advice on how to be a courteous, respectful gentleman? Here’s a gentleman’s guide to the ‘friend zone’…

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