I grew up not being great at giving compliments. This was because I often saw grown-ups around me deploy compliments in a fake, ritualistic way. This made me overcorrect by holding back my appreciation for other people's gifts as some kind of misguided rebellion against fake compliments.

There are many good reasons to compliment people. The most important reason is that it's important information transmission. I've found it hard to discern how good my choices are. Well-crafted compliments from friends and family have helped me make better choices.

This frame has helped me guide how I compliment people. I try to craft compliments in a way that maximises the transmission of useful and valuable information. I want the person I admire to know what the admirable thing is that they are doing so that they do more of it. It also opens doors to conversations that help me understand what helps people do admirable things and how they do it.

It starts with a feeling of admiration. Often this can be vague. I do not give a compliment when the admiration is raw and unformed. I instead observe the quality and actions invoking this admiration, which helps me articulate it more precisely. This articulation is the compliment that makes its way to the person.

Let's say you have a friend who is great at hosting people. Their track record of hosting the best get-togethers might strike you as unusually impressive. A common case is to let that thought get washed away in the humdrum of your daily life and not express this to the friend. This is a waste. No information transmitted.

You could possibly tell them, "Hey, enjoyed hanging out. Always great at your house." This is better. But we could go further. How about: "You are unusually good at hosting people. There is a warmth in your presence, and I notice you go out of the way to include people and make sure they are having a good time. And you do it in a way that looks effortless."

There are also bad "compliments". A person once told me, "your clothes make you look like a vintage wallpaper". Unfortunately, they didn't express what they thought of vintage wallpapers, so I couldn't make out if looking like one was a good or bad thing. Not much information was gained. There's also compliments like an unelaborated "dude, your eyebrows are so thick!", which depending on the beauty standards trend cycles could be insult or praise. Unclear information.

Good compliments transmit a lot of information to people who may not have been previously aware of what behaviours have made them stand out positively. I'm often surprised by how oblivious some people are to the virtues that are noticeably screaming out of them. In the case they were aware of these qualities already, a particularly well-crafted compliment will guide them to the specifics of what made that virtue tick. They might even explain their story or process behind what they are doing ("I think I'm able to do that because..."), which is useful information transmission to you.

A useful effect beyond just the information exchange is that it makes everyone involved closer and more personable. A good, genuine complimenter is a reliable person to me, because I know they are taking the effort to understand me and encourage the good in other people. This builds relationships.

However, there are still some things that I've yet to figure out with the art of the compliment.

In many situations, it's hard to come off as a genuine complimenter. Specificity in the compliment helps somewhat, but not fully. "Fake" complimenters have existed since time immemorial, and the lot of these people have misused them for flattery or other social status games. The effect of this is that some people will cast doubt on your compliment. This will make the attempted information transfer fail.

Receiving drive-by compliments can also be tricky. When complimented by someone I don't know well, there are roughly a few responses that I can think of: I acknowledge the compliment, but not so quickly that it appears dismissive; or I downplay the compliment which can come off as a rude denial or humblebragging. Both of these don't seem ideal. Without knowing the person well, I also am unsure of the motive behind the compliment and thus its validity. For now, I run under the assumption that people do mean what they say at some level and so I take every compliment seriously.

I also think some people genuinely don't want to be complimented, and will not appreciate the attempted information transfer. There are possibly many reasons for this, but one reason could be that they are steeped in a culture that's so insincere with their compliments that receiving one doesn't mean much, or worse, will be received with suspicion of an ulterior motive.