The Oldest Trick in the Book

Certainly one of the easiest ways to get into someone’s good graces is to compliment quickly and freely. This is ground zero for flattery and making people light up with a smile. If you think about it, you probably have positive thoughts about people running through your head all day, so there’s no reason not to simply give voice to them. We just tend to fixate on sneer-worthy aspects more than we like.

The Oldest Trick in the Book

Certainly one of the easiest ways to get into someone’s good graces is to compliment quickly and freely. This is ground zero for flattery and making people light up with a smile. If you think about it, you probably have positive thoughts about people running through your head all day, so there’s no reason not to simply give voice to them. We just tend to fixate on sneer-worthy aspects more than we like.

Within the world of compliments, there are two levels I want to differentiate between. The first level is the low-hanging fruit—there are only so many times someone can hear that they have nice eyes and still be impacted by it. This level is what most people are stuck on. They are more likely to be simple observations rather than in-depth statements. You’ll know the difference between the two types of compliments by the impact they have on the person. Eyes are great—but it’s something rather shallow to point out. There are only so many times you can hear that you have nice eyes and still care. How do you give compliments that are more thoughtful and less superficial?

The second level of compliment goes below the surface. For maximum impact, compliment people for two things (besides the obvious and superficial). Compliment people on (1) things they have control over and (2) things they have made a conscious choice about. There may be significant overlap between the two.

For instance, no one has control over the color of their eyes; thus, it’s not a very impactful compliment. However, someone may have made a very conscious choice to wear a specific hairstyle that takes an hour to get ready. Other examples include specific habits, words and phrases people use, distinct fashion sense, unique thoughts, and so on.

Why are these aspects so much more personal and impactful to compliment? Because they reflect the person’s thought processes and identity. These are choices people consciously make to represent themselves—their tastes and values. They don’t do it for others, but they are hoping to be judged positively and lauded for their choices. The more outrageous something might be, the more valuable positive confirmation is. Therefore, when you compliment someone on their choices and thoughts, you validate them to the highest degree. You’re telling them that you agree with them, it was all worth it, and they made the right choice!

You can see that complimenting a person on something they don’t have control over, such as their eye color, doesn’t amount to much other than “Hey, congratulations on winning the genetic lottery with your eyes!” Now, if this person was wearing colored contacts, it might be a better compliment because that’s obviously a choice they made to alter their original eye color.

Compliment things your conversation partner has obviously put some thought into. This might include a bright shirt, a distinctive handbag, an unusual piece of art, or a vintage car. These things are out of the ordinary, uncommon, and reflect a deliberate deviation from the norm. You never know if someone’s persona is ingrained in the fact that they choose to wear Hawaiian shirts. By complimenting someone on something they’ve clearly chosen with purpose, you acknowledge and validate the statement they have chosen to make about themselves.

Other things you can compliment people on that show individual choice are their manners, the way they phrase certain ideas, their opinions, their worldview, and their perspective.

Above all else, compliments trigger one of the most fundamental weaknesses humans have: we are starved for attention. We like to be put in the spotlight and given the attention that we feel we deserve. People aren’t really complimented that much on a daily basis—especially men.

We can easily see this because most people don’t know how to take a true and genuine compliment without a bit of awkward fumbling. Make it a goal to see people fumble about the compliments you give them—that means it impacts them more because they simply don’t get many, and it will have a greater effect on your relationship.

On a related matter, try to make it a habit to notice, point out, and celebrate people’s idiosyncrasies. Everyone has their own sort of either mental, emotional, or physical traits that make them uniquely them, and these can take unlimited forms.

You might think that these idiosyncrasies are things that people want to hide and conceal from others. But here’s the surprise: when you notice, point them out, and celebrate them, they’ll love you for it. In the context of conversation, it’s going to be things like their mannerisms, tics, gestures, body language, vocabulary, unique phrasing, or even how they cross their legs. There is a multitude of other possibilities. You just have to make sure that you frame it in a unique, positive, and fascinated light.

For instance, everyone has a different physical ritual they engage in, mostly subconsciously, when they speak to others. If it’s not a physical ritual during conversation, everyone has different ways they perceive and go about their day. Some people will chew fifty times for each mouthful of food. Others will avoid touching doorknobs when opening doors. And some might avoid stepping on cracks in the sidewalk for fun.

Once you have observed the same idiosyncrasy at least a few times to make sure it’s not because of a mosquito or some other environmental factor, draw attention to it! Not in a negative manner, but in an observant one.

• Hey, that’s an interesting way of tying your shoes…
• I see that you keep twisting the jars into patterns. Tell me about that.
• Do you favor your left arm? You crack it five times every time we walk inside.
• Did you read Nineteen Eighty-Four recently? You use the word “goodplus” a lot…

Make sure that you don’t have any judgmental tone in your voice or body language when you point out an idiosyncrasy. You’re not calling them out. It’s not negative. You’re just shining the spotlight on something that is personal to them that they thought people might not notice. But you did notice. The fact that you did will make them feel special because you’ve apparently paid so much attention to them. To continue with the above examples, what do you imagine the response will be? Very likely pleasant shock and a compulsion to open up and elaborate themselves to you.

Next, we turn to something that should be so foundational as to be taught in school from childhood, and yet…