When showing Charlie's confession in different places, there is a shot of the Rangers/Bruins game, however the person at center ice is wearing a Detroit Red Wings jersey.
There was a re-election in Season 3. New York Mayors are not allowed to serve more than 2 terms, so Mayor Winston could not be up for re-election here!
The Mayor is up for election for a third time, yet he mentions that it will be his second term in office!
Caitlin: How can you have a relationship based entirely on sex?
Charlie: My secret: lack of communication.
Stuart (to the Mayor): Sir, now that you and Claire have broken up, I just need to know: How was she?
Charlie: I was just thinking about the time the Mayor wanted to close down a strip club and Stuart chained himself to the brass pole...