How to give a sincere compliment

Carlton Boyce / 16 November 2018

The growing awareness of sexual harassment doesn’t mean you can never compliment anyone again, it just means you need to do so in a way that is respectful and sincere.



Giving a compliment used to be easy, didn’t it? You didn’t have to worry about offending anyone back in the day, so they came thick and fast, no matter what the environment.

But the fact that we didn’t used to worry about complimenting a woman doesn’t mean that our compliments were always welcome; a growing awareness of gender inequality over the years*, partly fuelled by the #MeToo movement, has taught us that any imbalance of power, whether real or perceived, has to be negotiated with care, respect, and a maturity that has all too often been lacking in both social and professional relationships in the past.

That doesn’t mean that you can’t compliment a woman though, it just means that you need to do it in a way that is respectful and sincere.

And not creepy, obviously…

*If you want to see how far we’ve come, try watching an old episode of The Sweeney.

First date rules

I’m not sure there are many compliments that are appropriate on a first date. I might end with something like “I’ve really enjoyed meeting you” but would I mention how attractive I find her, or tell her how much I like her shoes? Probably not; but I’d love to hear from our female readers whether I’m being unnecessarily cautious.

I’d feel much more comfortable complimenting her choice of food, or saying how much I admire her independence and spirit if she’s just returned from a solo holiday trekking around Tibet, but that’s because I’m then recognising her actions, rather than her appearance.

Which brings me neatly to my next point.

Don’t be personal

It sounds counter-intuitive but if you’re only dipping your toes into a new relationship then it’s better to compliment a person’s choices than their appearance. So, for example, you might say something like “I love your hairstyle” rather than “you have lovely hair”.

You might also think about saying how much you like the way they dress rather than saying that they look stunning. Choices, not appearance, see?

Comments about a person’s size or figure, no matter how well-intentioned they are, are a no-no. But I didn’t need to point that out, surely?

5 things you should never ask on a first date

Follow their lead

Let’s assume that you’ve mentioned how you love the coat she’s wearing. If she smiles and seems genuinely happy to hear it then you can probably give her another compliment or two in the relatively safe knowledge that you aren’t offending her or crossing a line she’d rather you didn’t.

However, if she seems embarrassed and closed in her response, it’s probably time to stop. Not everyone feels comfortable when a stranger (or near stranger, which is what you still are after a couple of dates) compliments them; we men sometimes find it hard to understand that our actions, no matter how innocent and well-intentioned, can intimidate others and make them feel threatened and uncomfortable.

(In the interests of balance I have to point out that this can work both ways; the only time I was ever scared as a prison governor was the first time I walked along the landing in a women’s prison to a chorus of Anglo-Saxon ‘compliments’. I still blush when I think about it but it did give me an insight into how vulnerable unwanted personal and sexualised comments can make you feel.)

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Be innovative

If a woman is beautiful, then she probably knows it and is sick and tired of being admired only for the way she looks. She is, after all, much more than a pretty face, so find something else to compliment her about. Talk about her vivacious personality, interesting hobbies, or boundless energy. Talk about something that she’s had to put some effort in to achieve rather than her luck in the genetic lottery.

(Although, if you’re brave and you’ve had a couple of dates that went well, you could try telling her that she’s the most beautiful woman you know - but consider following that up immediately with something else you genuinely appreciate about her, other than her looks.)

I once dated a fiercely intelligent woman who was fed up with being told how clever and hard-working she was. As it happened, she had a charming dimple that only appeared when she belly laughed. I thought it was enchanting and when I told her she said that no-one had ever mentioned it before, which left both of us feeling good.

Dressing for a first date

Talk about her accomplishments

Many women underestimate the contribution they make to their homes and families; most balance their work and home commitments without giving it a single thought and are used to having their hard work taken for granted.

So, if you’ve met her children, or visited her home, why not tell her what an amazing job you think she’s done of raising them? Or how beautiful her home is?

Ask for her opinion and advice

One of the most sincere and elegantly delivered compliments you can ever give is to ask for someone’s opinion or advice. Again, while I do hate to stereotype, not many men are comfortable asking a woman for a cake recipe or for help with a practical problem. (To be fair, we’re pretty rubbish at asking men for help too.)

If you can get past your macho pride you will have established yourself as a sensitive, supportive partner who isn’t afraid to share their problems or to take advice.

How to make a good first impression

Keep it simple

Looking into her eyes and telling her that she’s amazing is an easy way to tell her how you feel. Or simply say that you can’t think of anywhere you’d rather be at that moment than right there with her. Or tell her how easy she is to talk to.

Compliments don’t have to be complicated. Sometimes, it’s the simple stuff that means the most.

Compliments should be one-way

A compliment should be freely given, with no expectation of receiving anything in return. So, saying she has beautiful eyes doesn’t rack up brownie points that you can redeem later.

Just say what you’ve got to say and then move on; nothing feels more awkward than the silence that comes after receiving a compliment as it slowly dawns on you that the person giving it is expecting one in return…

Never joke about it

Giving a compliment in the form of a joke risks falling flat at best, and coming across as downright insulting at worst. Teasing rarely works with people you don’t know very well, either.

And while I say ‘never’, this is in the context of a new relationship. If mutual mickey-taking works for you both down the line, then that’s obviously fine.

Common dating mistakes to avoid

When it goes wrong

There is a risk that even the most carefully thought out compliment will fall flat; after weeks of admiring a new date’s blonde hair, for example, I mentioned it in another context with what I thought was subtle flattery. She went bright red and said that her hair was really auburn. We both went a bit quiet and then moved quickly on to another subject. Which is exactly how it should be done.

Please don’t make a big deal of apologising; just move along and pretend it didn’t happen. In this case the saying ‘least said, soonest mended’ really does apply!

Oh, and if you ever have to wonder whether a compliment was appropriate or not, then it probably wasn’t. And if she ever slaps your face you’ve got it very, very wrong indeed.

Compliments in a relationship

Of course, if you’re in a long-term relationship then all bets are off and you’d jolly well better be free with your compliments: first-date reticence has no place here.

How to be a better partner

Compliments in the workplace

Just no. Never, ever compliment a woman you work with on her appearance. There was a wonderful article recently in which the author told men to treat women they worked with in the same way as they would The Rock*.

The idea is simple: all you have to do is to replace your female colleagues in your mind’s eye with The Rock, and then treat them exactly as you would him. So, if you’d compliment a six foot, musclebound wrestler on being handsome, then please feel free to do the same to your colleagues. Otherwise just stick to telling them what a great job they’ve done and how much you appreciate their hard work.

If you’re still struggling with this one then just keep reminding yourself that your colleagues are there to help you get a job done, not to serve as your personal dating pool.

(Of course, we all know the person who sails through life complimenting anyone and everyone without ever causing offence. They’re a joy to work with and can brighten up even the greyest of days. The trouble is, people like that are one-in-a-million and the chances are that if you or I tried to be like them, it would backfire and there would be a queue a mile-long outside the head of HR’s office.)

*The Rock is the stage name of Dwayne Johnson, a semi-retired professional wrestler turned actor.

Complimenting strangers

One of the many advantages of growing older is that it frees us from the constraints that we often suffocate ourselves with, largely because any slightly awkward or odd behaviour will probably be chalked up to eccentricity.

So, if you see a stranger wearing a scarf in a fantastic print, or with a particularly well-behaved dog, feel free to mention it as you pass. Smile as you tell them and then walk away; the aim is to make them feel a little bit better than they did before they met you, not to get a telephone number and the promise of a date.

The Golden Rule

Finally, the Golden Rule is that it’s not so much what you say that matters as when and where you say it.

Telling your wife that her bum looks amazing is perfectly acceptable and probably a wise thing to say, but to say it to a woman on your first date is creepy and slightly sinister - and to say it to a colleague, is (and jolly well should be) a sackable offence.

So pick your moments, and deliver your compliment with a twinkle in your eye. Follow her lead, and relax into the relationship as it progresses. And please try not to worry; it can seem like a bit of a minefield but most women will accept a sincerely meant compliment gracefully, not matter how clumsily you deliver it!





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