Could this site be any less intuitive?
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Don't worry. You'll get used to everything soon enough:) .
well me and my friend can't figure out how to play against each other, very frustrating.
Dude, you haven't even figured out how to use the site correctly.
lol
For correspondence, top right hand corner there is a "play" dropdown. Click, "online" and then start a new game challenging him directly.
For live chess, again go to "play" and "live chess" then you should be able to find his name (under friends, or at worst in the list of all users online, from which you can add him as a friend by clicking the name and then "add as friend") and send a challenge.
I understand how some of the stuff might not be intuitive, but honestly it doesn't take long to get used to, and once you do it's a great place.
To add a friend, you go to their profile (chess.com/members/view/insertfriendyouwanttoaddhere), and in the right you will see a list of icons. Click the "add to friends list" one, and then give a reason for why you want to be friends with them. That person can either accept or decline the request.
Wow, most complicated chess site I have ever been to. No obvious way to add friends, invite friends to play a game with you, talk in the chat rooms... I understand how to get to chat rooms, it's just not intuitive at all. Of course, when I finally get in one, I get kicked out saying another login is detected, my friend just gets a white screen that has no controls and does nothing else.