When Richard (Edward Herrmann) and Emily (Kelly Bishop) invite Rory (Alexis Bledel) and Lorelai (Lauren Graham) to their very fancy tailgate party at the Harvard/Yale football game, Lorelai's innocent conversation with Richard's ex-fiancée Pennilyn Lott (guest star Linda Gehringer) leads Emily to deduce that Richard and Pennilyn have been meeting secretly for lunch for many years. Emily blows up at both Richard and Lorelai, prompting Lorelai to stop worrying about her mother's feelings and finally accept Jason's (Chris Eigeman) invitation to dinner. Meanwhile, Richard introduces Paris (Liza Weil) to his old classmate who is now a distinguished Yale professor (guest star Michael York).
- “One night in the hallway does not a true naked guy make, my friend”
- —Richard to Marty
- Marty meets Richard, Emily and Lorelai. Marty and Richard get along quite well.
- Richard sings with the Whiffenpoofs.
- Pennilyn Lott is seen and Lorelai meets her for the first time.
- Emily blames Lorelai for her fight with Richard.
- Rory sees Paris and Asher kissing.
- Rory – It seems a little wrong that Jessica Simpson is alive and well and Roy got eaten by his tiger
- Marty – (to Richard) Obi-Wan
- Lorelai – Ted Koppel's here