I would like to add my two cents to the House, Cuddy and Wilson love triangle or should I say fictitious love triangle? because now I'm not so convinced that House is pinning for Cuddy but having fun with Wilson.

House didn't get angry when he found out Wilson had taken Cuddy to the play nor he got jealous, he decided to have fun and mock Wilson instead. He tried so hard to convince Wilson he liked Cuddy because  it was his game of the week and Wilson, who knows House so well, did exactly what House wanted, admit he might have feelings for Cuddy so it was his turn to mock House. See House's expression during the scene, he's laughing inside. But once House's game is up, he moves to his next so appropriate victim, Cuddy, who falls for his story.

The whole conversation about May, December and October may translate to Cameron, House, Cuddy an Wilson.

Cuddy says she doesn't get the whole May-December thin, parallel to Cameron and House maybe?, but House doesn't agree with her,  he tells her to give them a break, May-October at worst, does he feel like October?, so Cuddy, who is obviously October, asks him why it can't be October-October, does she mean her and House or her and Wilson? but House responds "May is when things start to get hot", Cameron anyone? then he shuts her down by asking her to a play with him, there's no play, he's testing her, wanting to know about her going out with Wilson, make her talk, same thing he's done with Wilson before, except now it's her side of the story, so he can mess up with her mind and continue to have fun.