“I keep finding myself in positions where I’d really like to compliment someone but am afraid of coming across as creepy, sycophantic, patronising, and/or a thousand other awful things, and it’s annoying me. What do you think are the rules, if any, of giving compliments? What sort of things do you love to hear from others, and what sort make you cringe? (Advice on how to graciously receive compliments would be very much appreciated as well.)”

First of all, kudos for your urge to praise others! I think that says very good things about you.

Let’s face it, everyone loves a compliment. Even if we are shy, insecure or suspicious of someone’s motives, it still works. It makes us smile. We feel good about ourselves. It’s a lovely thing.

Giving a compliment is simple in theory: you just open your mouth & say something positive! But sometimes we second-guess ourselves, worry about what other people will think, doubt our own authenticity & get into a panic. It’s no fun to get into a flap over something which is so charming, harmless & sweet!

Here are a few tips to get you on your way!

Be sincere
The number one thing that will trip up your attempts at giving a compliment is lack of sincerity! But really, think about it. Why would you say something unless you meant it, anyway? Sincerity is a fine thing, & people will respect you for it.

I used to go to school with a girl who would flash you a big smile & then as soon as your back was turned, she would flick her smile off. It was all for show. It made me dislike & distrust her. It’s all about being sincere. Giving faux-compliments, like the fake smile, is a social fumble of the highest order. People will know! Don’t think they won’t! If you want to be seen as a genuine person — & most of us do — you need to be real!

What does this really mean? It means don’t lie. It means don’t just say something because you think your friend wants to hear it. & don’t give a compliment if underneath it all you have an ulterior motive! Telling every girl in the room that she’s “hot” just because you don’t want to go home alone isn’t kosher.

Your compliment will go over best if people feel like you’re just saying it because it’s true, & that it’s coming from a place of honesty, truth & love. It’s always better to give fewer, more sincere compliments than to spread them thick like peanut butter & without integrity.

Think about what you’re saying
When it comes to giving a compliment, think back on the compliments you have received which actually meant something to you. Often, as women, these comments come from the opposite sex (for whatever reason). So cast your mind back. What has more of an impact — “You’re hot” or “You have beautiful eyes”? How about “You look nice” versus “You have legs for miles”?

Of course, any kind of compliment is wonderful to receive. But if you really want someone to remember it (& you) fondly, it’s best to put a little bit of thought into it. In the above examples, my vote goes to the two latter compliments. Why? Well, because whoever said it actually thought about it. It’s not just a platitude — they gave it some consideration before they said it.

But this cuts both ways. Let’s say you’ve just met this cute girl whose best feature — in your opinion — is her adorable nose. What would you say to her? While your first impulse might just be to blurt out, “Nice schnozz!”, curb your enthusiasm! A seemingly random compliment with little to no context can be confusing & sometimes unintentionally offensive. What if said cute girl has a complex about her nose? She might think you’re being sarcastic or making fun of her, & that is not going to go over well at all! However, if you take a second, think about it, breathe, & then say, “Your nose is utterly kissable”, you’ll find her response is probably a lot more positive!

Make it mostly about them, but a little bit about you
What the hell does that mean? Does that mean giving a compliment quickly as an excuse to prattle on about yourself for an hour? No! It means talk about them, but give a bit of yourself away too. Make yourself vulnerable. Invite them in to your life.

An example? “You’re a good writer” is a standard compliment. It’s flattering, but not ground-shaking. “Your writing has changed my life” is totally different. The recipient of the comment will be shocked, thrilled, delighted — & they will want to know more. You can start having a real conversation where you both reveal things about yourselves, & isn’t that the ultimate goal? To allow the relationship to blossom & unfurl in a more deeply meaningful way?

Don’t be too obvious
If you met them, you might be tempted to compliment Pamela Anderson on her enhanced mammaries, praise Robin Williams for being so hilarious, or congratulate Donald Trump for his success. These things are obvious, so of course they would be the first things to pop into your head. But if you give it a moment, you’ll realise that these people have heard all that before. Pamela knows she is the bouncing babe from Baywatch. Robin is aware that he’s funny. & Donald is very cognizant that he is a wealthy man.

If you want to stand out or make any kind of impact on them, you need to say something else. Something different. Make it easy for them — what can they realistically say when you tell them something about themselves that they already know?

So do a bit of research. Give it some thought. A trivial amount of searching reveals the fact that Pamela Anderson is a tireless crusader for animal rights, while Robin Williams is obsessed (obsessed!) with video games & cycling. & you may not know it, but Donald Trump is strongly opposed to the war (&, uh, Rosie O’Donnell!). If you can engage someone in conversation on one of their passionate — but less obvious — causes, you have got it made.

The more you do it, the easier it becomes
As with anything, the more you do it, the less terrifying it becomes. Imagine one day being able to graciously compliment people on the fly! It could be you!

The thing is, it’s really not that difficult. It’s trivial to smile at someone & tell them you like their shoes, praise them for their choice of headwear or compliment them on how well-mannered their dog is. They will smile, you will feel good about yourself, & who knows? It could be the beginning of a marvellous relationship.

One of my most invigorating experiences in NYC so far was when I was sitting down in a raw food restaurant, eating. A girl sat near me & told me she loved my tattoos. We got talking, & it turns out she is a stylist & fashion editor for the likes of Vogue Russia & Harpers Bazaar. Since meeting in that restaurant, we have been to art parties in Brooklyn, cruised highways while talking about shoes & blown bubbles at passers-by in Times Square. It all started with a compliment, so don’t be afraid! It can take you to amazing places!

Realistically, most people, if complimented, will respond positively to you. The only reason why they wouldn’t would probably be if they were insecure, suspicious, bitter or had decided they didn’t like you! (What a pity for them!) If someone doesn’t accept a compliment from you, don’t sweat it. It’s their stuff — not yours!

Now, onto the much less complicated business of…

Take this quick & easy quiz to test your compliment-receiving skills!

Your friend says, “You have a lovely complexion.”
You reply…
A. “Oh, no I don’t, I hate my freckles…”
B. “Thank you!”

Your secret crush whispers, “You are a treasure in the shape of a girl.”
You respond…
A. “Haha, whatever! You must be blind.”
B. “Thanks!”

A fine-lookin’ stranger smiles before saying, “You are the most fabulously dressed person I have seen all week.”
You exclaim…
A. “Um… when’s the bus coming, again?”
B. “Thank you!”

You guessed it. Your answer should always be B. Even if you don’t believe them. Even if you don’t feel that it’s true. Even if you think they are delusional, mental, crazy! Just say THANK YOU. Who knows? One day, you might realise how amazing you really are…