If you know your friend is on at the same time, I believe you can issue a challenge (there used to be a list of everyone who was on at that moment, and you could click on their name to challenge them, but that's been taken out for some reason).
Hope that helps!
I am sure it can be done, but i can't figure out how to play live chess against a friend of my on chess.com. can somone help me out?
Thank you,
Tom