The scene where Wilson suggests he may have made a pass at Cameron is in the episode 'Role Model', the one where the black senator is running for President.
I don't have an answer to your second question, and it's been bugging me because I know that I know. It's a good excuse to rewatch the first season dvd set though, so when I find it I'll post.
Sorry I couldn't help more (and I call myself a House fan...<shakes head>)
