Pretty is most often used to describe women and girls. Usually, men who are described as pretty are attractive in a less rugged way. The term "pretty boy" is used to describe men who take care of their appearance in a way that is often more associated with women. They are usually clean shaven and well dressed. "Pretty boy" can be used in a negative way to imply that a man is not very masculine. For example, "He's too much of a pretty boy to get his hands dirty changing a tyre." But simply describing a man as pretty is not negative.

And to supplement all the wonderful answers, I'll just say that some very masculine men are just naturally pretty - they have big beautiful eyes of a striking color, thick lashes, full lips, high cheekbones, small perky noses, and other delicate features that usually define female beauty. To give you an example, Jason Momoa, who played Khal Drogo in Game of Thrones is a very handsome man - he has very rugged, masculine features: https://www.refinery29.com/en-us/2017/02/139696/jason-momoa-baywatch-before-game-of-thrones-khal-drogo On the other hand, this guy, whom I don't know, is what I would consider pretty: http://chataboutheroesrp.wikia.com/wiki/File:Blue-boy-eyes-greece-love-Favim_com-354715.jpg By the same token, women, especially older women, who are not necessarily beautiful, but have a commanding presence, stately beauty, can be described as handsome.

Hey Katya, I would follow Shantay's explanation, using the word pretty on a man does not necessarily mean something negative, in fact many TV shows and kids TV shows have used it on male characters. Although it is true that pretty is mostly used for women it can also be used on men, depending on the context. You can joke around with your male friends and call them pretty either to make fun of them, get on their nerves or to actually give them a compliment! If someone called my face pretty I would take is a complement. I myself call my parter pretty often. So it really depends! If you want to play it safe, stick to using pretty for women and handsome for men, but as you become more comfortable with the language don't be afraid to use pretty on males as well!

I would say that there is usually a negative implication in describing a man as pretty, except in some specific contexts where it is OK or desirable to be seen as less masculine. Both of the examples quoted have negative implications. It is a word generally used of women. I wouldnt use it of a man.

Both of them are used to commend. But, I'm man, then I use "pretty" and "beautiful" to commend the women!! I hope it helps!!