#1 Be Unique The best compliments feel tailor-made. Etiquette expert Diane Gottsman warns that generic compliments that could apply to anyone, like “you’ve got a nice smile” or “your hair is pretty”, often come across as superficial. A good compliment demonstrates that you’ve made an effort to get to know her.

#2 Be Sincere This might seem like a no-brainer, but don’t compliment her unless you really mean everything that you’re saying. Insincere compliments can make you seem disingenuous, or worse – like you see the compliment as an obligation. In other words, a genuine compliment might as well be worth its weight in gold!

#3 Don’t Just Compliment Physical Appearance According to psychologist Michele Barton, Ph.D., exclusively giving compliments about a woman’s physical appearance can “sound generic and insincere”. When you’re complimenting a woman, don’t forget to consider  the aspects of her personality that you appreciate.

#4 Don’t Be Too Literal Researchers reported that vocabulary use is actually one of the ways that humans select potential mates. Generally speaking, the size of your vocabulary correlates strongly with your intelligence level. Putting all those vocabulary words into practice in your compliments can subtly demonstrate that you’re intelligent, educated, and eloquent!

#5 Beware of Backhanded Compliments Here’s an easy tip to help you avoid accidentally doling out a backhanded compliment: never add a qualifier to your compliment. If you think a woman is beautiful, just say that she’s beautiful — no need to say that she’s pretty

#6 Context is Key To many women, being approached by a strange man in public, even if he’s saying something nice, can be a frightening experience. From a very early age, many women are trained to learn tricks to stay safe while walking alone, especially at night.

#7 Catcalls Are NOT Compliments Whistling, shouting, honking, or commenting on the physical  appearances of women on the street are all completely inappropriate  behavior. Whistling, shouting, honking, or commenting on the physical appearances of women on the street are all completely inappropriate behavior.