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Situation:

Yesterday I was instructed to go to a small conference several of my colleagues were attending. It was short in duration and gave everyone the opportunity to socialize a bit after it was finished.

I talked with my new friend (female) again and noticed her makeup. It wasn’t unusual since I last saw her; but, I was especially impressed to compliment her this time. She had really put time into making it look nice and you could definitely see her skill.

Over analyzing my situation, I never actually managed to say anything for fear of a negative response.

Analysis and Goals:

Those of my friends who wear makeup do so for many reasons (insecurities, entertainment, and impressions to name a few).

It’s not necessarily like an article of apparel. Clothing is more impersonal than something that’s put on a main feature of human physique (the face).

What’s concerning is unintentionally making the wearer feel more insecure. Or maybe possessing them with the idea that they should always wear it to receive approval.

The objective is to let them know that: hey, I can really appreciate that you elected to put makeup on and how you orchestrated that decision. The intention is not to make them feel they need my approval or that they need to wear it. I want them to know it’s their choice.

Summary:

It’s been established that makeup can be a sensitive topic. My intentions are to make my friend feel happy about my compliment and receive a positive response.

How would I compliment a woman’s makeup without making her feel negatively in the ways I’ve mentioned above?

  • 5
    Q: 1. can you tell us if you're male/female? (it's a completely different small talk when FF or MF and POV can be differently welcomed). 2. how old is she? (big difference: show some or hide some) – OldPadawan Jan 19 at 7:33
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    I'm voting to close this question as off-topic because its goal is to be a "reference answer", and that's far too broad and opinion-based. It should be narrowed down to a specific question with a clearly identified goal. – OldPadawan Jan 19 at 17:42
  • Have you ever actually tried to compliment a woman's makeup just as you would a piece of her clothing? If so, how did it go? – Kat Jan 22 at 0:33
  • I rarely wear eye makeup but one day I had both a close friend and a cashier at a drug store say, "Wow, I love your eye makeup!" I didn't take offense at either. I would say then you pay attention to if the colleague takes offense easily or not. If not, then compliment their skill. If they seem to take offense easily, then I would have to admire silently and keep my thoughts to myself. Years ago, when I was a corporate trainer, I asked a kind-hearted student after several days in class, which brand of makeup was she wearing, because it looked great. She took it as a sincere compliment. – Laura Jan 29 at 22:37
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TL;DR

Focus on her skills or the tastes she has, not on how she looks.


Background

I'm a woman, I don't wear makeup (and never did for various reasons). However, some people still complement the clothes I'm wearing from time to time and I think complementing clothes or makeup is mostly the same thing.

A little story first

When my family tells me:

You look so nice in this, you should wear it more often.

I don't like it. I feel as if I have to please them by how I look and I really don't appreciate it.

One day, I was walking in the street, when I distinctively hear and saw a man looking at my pants (a sarouel) and telling his friends:

Wahoo, her sarouel is so cool!

I was very pleased with that. Because, instead of judging my looks, they were judging my taste and, even though it's fine to not have the same taste, it's always nice to find someone who likes the same things as you.

What about makeup?

So, to transpose this to makeup, you could say something like:

You know, I really like the color you choose for your lipstick.

Here, you are not judging her look, but just stating that you really like her lipstick color, which implicitly means: "I really like your taste".

Another technique

Another technic could be to focus on her skills. I do some drawing and coloring and I always like when people tell me how they are impressed by my skills.

I believe makeup to be quite similar to coloring and, if you know enough about the art of makeup, you can compliment this woman skills on that.

(I was going to put an example here, but I really don't know enough about makeup to do that).

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