You might not remember the best compliment you ever received, but you might remember the worst. Instead of feeling flattered and happy, you felt annoyed and a little resentful. Or you might have wondered whether the remark was a compliment at all, or in fact the opposite, intended to put you in your place. This brief guide to the 9 types of compliments will help you make sure that your compliments make you and the recipient feel a little bit better about yourselves, and your relationship that much richer.

1. The ambiguous compliment. Let’s start with the case when your language leaves a little something to be desired: “A good meal from you is a rare treat.”  What you meant to say is that the meal was a treat that you rarely are ever able to have from anyone else, but instead it sounds like you meant that it’s rare for the cook to do a good job.  The problem is that “rare” can have more than more than one meaning, making it lexically ambiguous.  To avoid this type of inadvertent insult, make sure that you think about what you’re going to say, and possible double meanings, before you utter it. In general, this is a good rule of thumb in all communications, but especially when you’re discussing a sensitive matter.
2. The too-frequent compliment. Compliments can be subject to the laws of economics, meaning that the more often you give them out, the less they mean. By giving nonstop compliments, you seem insincere, and even if you genuinely feel this way, it would be best to keep some of those words of admiration to yourself. Also, the down side of giving too many compliments is that people come to expect them from you. Should you fail to notice something they actually would like to hear complimented, they’ll think something is wrong.
3. The inappropriate compliment. Unless you are extremely close to your recipient, it’s not wise to overstep the boundaries of professional or even personal relationships by noting some aspect of an individual’s appearance or talents that presumes over-familiarity. In some cases, people may be trying to use the compliment to manipulate the situation so that they seem even closer than they are in reality, either in terms of their emotional connection or their status.  A boss can’t exactly complain if you say you like his shoes, but he might feel a little uncomfortable because he doesn’t feel you have a personal enough relationship to comment on his appearance.  Even telling your boss she handled an awkward situation well, though perhaps said in earnest admiration, would also seem a bit inappropriate given that your boss is a boss because (we would hope) she knows how to deal with these situations. However, if your boss asks for this kind of feedback, by all means give it because to not do so would be rude. Just make sure you are positive, supportive, and careful in the words you choose (no rare treats, please!).
4. The envious compliment. Perhaps an acquaintance or co-worker has something that you both (a) love and (b) want. It could be an item of clothing or jewelry, a hair style, or skill. Your desire to express admiration mixes with your desire to have said thing or personal quality and now you’ve made the recipient feel uncomfortable.  He or she worries that you will try to get this out of your hands (if it’s a thing) or will perhaps stalk you until you figure out how to gain that quality yourself. In either case, it makes you look jealous and resentful. Better to say you like something (as long as you haven’t overstepped boundaries) and, if it’s a thing, maybe indicate that you’ve been looking for something similar and wondered where it came from. Don’t expect a ready answer, though, or even an easy one (“It’s been in the family for years,” or “I just dug it out of the closet”). If what you’re complimenting is a skill, you might phrase the question in terms of a comment about yourself (“I’ve always had trouble with public speaking”) but don’t push the person too hard to find out how to be just like him or her. You might ask for feedback on a future occasion about how to improve yourself, and hope to get some good advice in the process.
5. The awkward compliment. Many compliments in the above categories can produce a sense of awkwardness, but we still need to deal specifically with the cringe-worthy variety. This might be one given to one person in front of a set of other people who themselves are not being complimented.  The other people wonder what’s wrong with them, and the person getting the compliment feels bad that he or she’s been singled out for your admiration.   Speaking of other people being around, if there are 3 of you in a situation of whom 2 are in a relationship, be careful. Telling the cook that his stew is “the best you’ve ever had” (again, not a rare treat) when your own stew-cooking partner is sitting right there taking in the same meal will only make your partner feel angry and hurt. You can’t take the compliment back (which would be even more awkward), but you could make a note to self that on the next occasion you should stay away from handing out your acclaim publicly in front of others who may be hurt by your words of intended kindness.
6. The compliment that’s on the wrong set of qualities.  Praising people for qualities relevant to a situation may help motivate them and also feel good about themselves.  However, giving an off-topic compliment can get them off their game by leading them to develop self-doubts. In a study of compliments collected from college students, Rees-Miller (2011) found that men tend to praise other men for their competence and women praise each other on their appearance when in social situations. However, when working on work-related tasks, both men and women gave compliments directed at the other person’s competence.  If you compliment people based on their appearance when, in fact, they would prefer to be complimented on their performance, this reinforces the notion that their performance is not valued and they may doubt their own abilities.  Compliments that reinforce a positive stereotype about a gender, racial, or ethnic group can also create bad relationships.  Siy and Cheryan (2013) conducted a series of studies in which they showed that people can feel depersonalized by compliments such as “Asians are good at math” or “women are nurturing.”  Your compliment, though well-intentioned, makes the person feel less like an individual and more like a member of a targeted social group.
7. The unintentionally rude compliment.  Assuming that you want your compliment to reflect truly positive feelings, you need to monitor not just what you say, but how you say it. A compliment offered in a condescending tone of voice conveys your belief, intentional or not, that you’re surprised at the recipient’s ability to do something well.  Similarly, compliments can sound sarcastic if you don’t have the right emphasis: “Oh, what a great job you’ve done!” can mean the exact opposite if said in the wrong tone of voice.  You can also inadvertently insult someone who’s had a major life change, such as losing or gaining weight, having cosmetic surgery, or completed a training course by remarking on how much better he or she looks or performs. These compliments are risky, unless you know the other person very, very well (and are ready to apologize if you’re misunderstood).
8. The sales pitch compliment. If it’s clear that you and the recipient stand to gain from your compliment, your compliment may seem insincere.  The suck-up compliment is one of the oldest tricks in the book among salepersons and people in service industries, and it’s not an unheard-of strategy to use on the families of prospective long-term relationship partners. A study by Seiter and Weger (2010) showed that dining room servers received higher tips if they flattered their patrons (up to a point).  Similarly, Grant et al (2010) found that people are more likely to comply with those who flatter them. The fact that these results didn’t surprise you (I’m assuming) should also make you aware of the need to be up front about those compliments you can’t resist making to the people whose hold the power to make you richer, either emotionally or financially. By the same token, if you’re the recipient of the suck-up or sales pitch compliment, recognize what’s happening, and you’ll be better able to resist its lure.
9. The right compliment. You’ve already learned a great deal about how to give a good compliment (see how smart you are?).  OK, just kidding.  The right compliment is sincere, respectful, is meted out in the right doses, and provides no obvious benefit to the giver.  I doubt if there’s any research on this at all, but I am willing to guess that a great compliment turns on the brain’s reward center, leading to a flood of good feelings not only about you but- more importantly- the recipient of that praise you are so eager to share.

Unfortunately, few people truly know how to give great compliments. Even if you did, it’s hard to know that it was, in fact, the perfect compliment. No one is going to compliment you on your compliments but they’ll react pretty negatively to the ones that fail. You can, however, gauge whether you’ve hit the intended mark (or not) by taking an honest look at your recipient’s face and response. The next time you make a compliment to that person, chances are you’ll boost their self-esteem, and yours.