Jack & Bobby Season 1 Episode 5 The First Lady ( Air Date 2004-10-10 ) Genre Drama category. Overview "The future reveals a dark secret about the first lady. Back in the present, Jack offers to escort a depressed Courtney to her father's work fundraiser leading to an unexpected confession and kiss. Meanwhile, much to the consternation of her sons, Grace offers to let a homeless man stay at their house for a few days until she can find him a better place to live.".