Go on live, then click the "friends" tab, and challenge him from there.
playing live against friends
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i had same prob.. go to main hall, ask ur frnd to type a mess n challenge him or go to friends, chaleenge
If you look them up first http://www.chess.com/members/ and add them to friends from their homepage, they'll be easy to find in live chess
How can I play live chess against a particular opponent? I want to be able to meet a friend on line and play live.