How to Compliment a Woman's Personality

Complimenting a Romantic Interest

Don’t give one too soon. Unless you are responding to an online dating profile or mutual friends set you up on a date, have at least one pleasant, personal conversation with her before you try to compliment her character traits. Give her a chance to tell you about herself before indicating you know her in a personal way, even if your mutual friend has spoken profusely about her great qualities. Say "Roger told me you are really into volunteering," for example, instead of "You are a really generous person!" If she is already a good friend of yours, and you suddenly start wanting a relationship, be especially careful about starting off too strong too quickly.

Avoid singling her out in groups. You have mutual friends, and are hanging out with the woman you like. Giving her compliments in front of others might make her feel put on the spot. Save it for when you two are speaking privately.

Highlight what makes her unique. Even comments about one’s personality can seem insincere if they are too common or obvious. Point out to her something that makes her an individual who you want to get to know better. Never use a cliché or obvious pick-up line. “I’ve never met anyone like you before,” or “You are a real keeper” are not compliments. If you can’t think of a compliment that doesn’t sound rehearsed or looked up online, opt not to give one at all. Be specific when complimenting her sense of humor. What exactly about it is so awesome--her snarkiness, her ability to make puns hilarious when no one else can, or that it’s so similar to you own?

Make sure your comment is relevant. It should flow with the conversation or be related to what you are doing at that moment. Bringing up something wonderful about her character out of the blue will likely either make her uncomfortable by indicating your romantic feelings, or sound insincere. Wait to tell her how much you admire her intelligence until you are having a philosophical discussion or watching a political debate, etc., not during a game of Ultimate Frisbee.

Note why this trait is important to you. She can have lots of good qualities that a lot of people won’t care about. Make sure she knows you are sincere by briefly stating why you care that she volunteers at the homeless shelter or goes regularly to the Buddhist meditation group nearby. #* If you don’t make a connection to her great quality or characteristic, then you are just giving false flattery.

Keep it short and sweet. A well-received compliment is succinct. You need two sentences at most—one to tell her what you admire about her and a second to qualify why this trait matters to you as a person. Don’t give a whole treatise on how smart she is. She probably knows she’s smart and doesn’t need you to convince her. Keep your compliments down to earth. Don’t “put her on a pedestal.” Even if you think she’s the most amazingly intelligent woman you’ve ever met, avoid such generalizations. Think about how a celebrity might feel when a starstruck fan standing behind them in a long line at Starbucks starts delivering a ten minute speech about how amazing they are. Don’t overdo it. If you are constantly giving this woman praise, it will start to come off as insincere or forced. Also, when you give out compliments all the time, they mean less. She might come to expect them and be hurt when you stop trying so hard.

Ensure your language is clear. Sometimes what we mean to say doesn’t come out the way we meant it. A lot of words have double meanings or multiple uses that make them ambiguous. Make sure you are clearly stating what you mean so that she can’t take it the wrong way. ”I love your rare [insert quality].” Is it rare in the general population, rarely a quality attributed to women, or rare as far as her typical behavior? Instead, say “I think its wonderful that you are so [same quality] because you inspire everyone around you to be that too." Also make sure you aren’t accidentally giving a back-handed compliment. “Wow, you are really funny today,” feels like “You aren’t usually funny at all. What a surprise!”

Don’t expect a response or gift-in-kind. Give her a compliment because you admire her and want her to know, not so she will go out with you or think you’re good dating material. Avoid “nice guy syndrome.” Don’t be nice to a girl and expect her to reward you by going out with you. You should be nice because she’s a person, like you, and deserves respect.

Offering Compliments in Professional or Formal Settings

Be careful not to overstep your boundaries. Avoid compliments that are too familiar or inappropriate when praising your co-worker’s performance or your mother-in-law’s exceptional family values. You are trying to make her feel good about herself and associate you with this positive self-image, not make her self-conscious or feel threatened. Just like it would be inappropriate to tell a co-worker how sexy she is (regardless of any positive personality trait you try to pair this with), you wouldn’t tell her you bet she’s a really great wife no matter what you know about her marriage. Praising your boss with, “That was an especially difficult meeting and you handled it with grace and assertiveness,” is much better than saying “Those guys were really gunning for you, but you really whipped them into shape!” Tell your mother-in-law that she should be proud for raising a strong and compassionate, well-rounded daughter, rather than just saying she must be a good mom and/or wife. The first praises her for her character strengths and passing those on, the second implies her identity is based on her ability to play a stereotypical female role well.

Don’t compare what she is now to what she was before. In the same way that telling a woman, “Wow, you lost a lot of weight! You look great now!” can send her into a spiral of self-consciousness about others noticing her weight before, saying a co-worker is “really good at ___ now” references the fact that you didn’t think she was before. Concentrate on the present, not what you thought she was like before said improvement. Watch your tone. It’s incredibly easy to sound insincere when complimenting someone you don’t know very well and want to impress. Saying the same thing in a different tone could come off as sarcasm or spite. Likewise, don’t sound overly excited or it will feel forced or superficial. Imagine her saying it to you first.

Give compliments that are selfless. No sincere compliment should ever benefit you, as the giver, at least not in an obvious manner. Consider compliments gifts given for no reason. Tell your aunt she's excellent at creating her own dishes after having dinner at her house because you honestly enjoyed the meal, not so she will invite you again tomorrow. Avoid fishing for a return compliment. Yes, you may want to impress or endear this woman to you, but your compliment should not make her feel like she is expected to give you one in return.

Avoid unintentional condescension, especially if you are male. You can ruin a perfectly good compliment by adding a diminutive like "sweetie," "honey," or "girl" at the beginning or end. Also, be careful not to give unsolicited compliments without an appropriate catalyst. Telling your boss "You are really great at managing people" as you pass her in the lunchroom is not the best opportunity to show appreciation. Wait until she demonstrates that skill. A good rule is to refrain from giving a female co-worker or academic partner any compliment you wouldn't give to another male.

Complimenting Other Women as a Woman

Avoid envious overtones. Whether a co-worker you admire or your new mother-in-law, be sure to state your compliment in a manner that acknowledges her good qualities or successes without sounding like her new biggest fan. She may feel threatened by any suggested ambition to take her place in the office or in her place as the most important woman in her son’s life. No one wants to be around someone who wants to be just like them. Instead, let her know that her traits inspire you to become a better version of yourself.

Don’t reinforce a stereotype. Women predominantly compliment other women on their appearance, which enforces gender stereotypes instead of acknowledging her individuality. Make a practice of starting conversations with another woman off with a compliment on her character or achievements before mentioning you love her outfit. And make sure it isn’t reflective of a stereotype or social constraint. Imagine her saying it to you first and assess how you would feel. Don't qualify a great compliment with "For a woman, you are really great at..." or "Most girls can't do ______ well." Instead of telling a stay-at-home mom she is great at managing her kids and husband, tell her you are amazed by her ability to manage time or multi-task. Make what you say about her, not about how well she fits into a traditional female role.

Be sincere. Suck-up compliments can be good sales techniques for business people and customer service related jobs. But nobody wants to work with the car salesman that is obviously schmoozing them. Likewise, your fiancé’s sister doesn’t need to be your new bff. Only give compliments when you really want to, and mean them, not to “sell” yourself to them.

Qualify any comments on her appearance as evidence of a great character trait. Women tend to compliment other women on appearance right away, even though they would rather be complimented on character or performance. Tell her she looks like she could take over the company in that amazing outfit, instead of just saying you like her suit. Qualifying this physical compliment in this way can make her feel proud for promoting an image of herself as an intelligent, ambitious, and strong-willed business woman in a predominantly male-run field.