Wasn't Wilson present at the Thanksgiving in the occasion when Cuddy sent House to get a turkey sandwich? I also cannot recall in which season he and Cuddy went out to the art show, but it seemed they enjoyed spending time together (although, perhaps, not the art itself).
OT: I believe that her voting for Wilson in the Vogler arc, just as her vote against House, aren't a sign of her friendship or lack thereof but of what she thinks is best for PPTH. In fact, what I got from that episode was that she was willing to put the good of the hospital before her personal liking (it's clear she doesn't like Vogler, but as head administrator she knows how much she could do with his money)
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I also cannot recall in which season he and Cuddy went out to the art show, but it seemed they enjoyed spending time together (although, perhaps, not the art itself).
OT: I believe that her voting for Wilson in the Vogler arc, just as her vote against House, aren't a sign of her friendship or lack thereof but of what she thinks is best for PPTH. In fact, what I got from that episode was that she was willing to put the good of the hospital before her personal liking (it's clear she doesn't like Vogler, but as head administrator she knows how much she could do with his money)