Jack walks in on Grace and Tom (Bradley Cooper) in a compromising situation and tells Grace he disapproves of her romance. Meanwhile, Bobby convinces Grace to allow him to attend an overnight hunting trip with Peter by blackmailing her on telling Jack about her relationship with Tom before he finds out, which proves to be an eye-opening experience for Bobby. Also, Courtney contemplates moving her relationship with Nate (guest-star Mike Erwin) forward and does this by making him her first sexual experience. Lastly, Jack hangs out with new friend Katie (guest-star Kate Mara) as he adjusts to Missy and Randy (guest-star Cam Gigandet) now coming together.
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