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.
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. [6] X Research source 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?
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. [7] X Research source
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. ”[11] X Research source 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. [12] X Research source
”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!”
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.
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.
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.
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.
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.
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.
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.
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.