The Fool Who Sees Clearly
Allan Sepinwall commented that if Jeff could see clearly enough that Chuck and Sarah need to get together, he expects them to do so soon.
Which would be a good thing.
Jeff, playing the fool
Jeff is a fantastic character. He is Chuck's Shakespearian fool: The only one who can safely speak the truth for the audience without giving away anything to his fellow characters.
This is definitely an element to keep in mind for your productions. Not only does "the Fool" have a long literary history as a character, but he is a great tool for communicating something to your audience when your other characters can't/won't admit it.
Your Media Production Mentor