I never watched that episode but I watched the clip when he says goodbye to Chimecho.
It was actually genuinely sad when he said "I don't know how to deal with this". James is probably the only character who could pull that off though, given that it's JAMES
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http://sphotos.ak.fbcdn.net/hphotos-ak-ash1/hs462.ash1/25378_426337043573_299696888573_5469519_6175407_n.jpg