You should both go to live chess. On live chess there is an area of tabs which say things such as chat and friends. Click on friends. You will see his name on to the right it will say something like challenge. Click on that
How to play a friend on live chess
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How would I play a friend on a timed game? So far, we've only been able to play via 'online chess' mode. I've tried to challenge when he's online but the options only give me the basic Online 1 day, 2 day etc.
Thanks