Season 3, Episode 17:
Catch-22
In flashbacks, Desmond spends time in a monastery after leaving his fiancée, Ruth, a week before their wedding. After Ruth calls him a coward, Desmond gets drunk on the monastery's wine, and is fired by Brother Campbell, although he asks him to bring some wine to a customer before he leaves. The customer turns out to be Penny, who asks him to come with her to Carlisle to deliver the wine.
On the Island, Kate and Sawyer have sex in Sawyer's tent, while Jack and Juliet grow closer. Afterwards, Sawyer suspects that Kate only slept with him out of jealousy of Jack and Juliet, and accuses her of using him.
Meanwhile, Desmond has another flash of the future, seeing Charlie shot and killed by an arrow from one of Rousseau's traps, as well as disconnected visions implying Penny is coming to the Island. He gathers the people he saw in the vision, Hurley, Jin and Charlie, and they set off into the jungle, following the cable buried on the beach. At night, they see a helicopter crash into the ocean, and a person parachute out of it. When the time comes for Charlie to die, Desmond saves him. They find the parachutist, hanging from a tree. They cut her down, to discover that she is not Penny, although she does know Desmond's name.
Tropes in this episode include:
- Apologetic Attacker: Ruth's brother Derek apologizes to Brother Campbell immediately after punching Desmond.
- Flashback to Catchphrase: Desmond's time in the monastery explains where he picked up his habit of calling people "brother".
- Freeze-Frame Bonus: A picture of Brother Campbell with Ms. Hawking can be seen on his desk, implying that he too is seeking to put Desmond on his fated path, which is supported by the fact that he sets up Desmond's first meeting with Penny in the final flashback.
- Friend-or-Idol Decision: Desmond, realizing that his visions of the future may change entirely if he tries to change anything about them, is left to choose between saving Charlie, and risking preventing the parachutist, who he believes is Penny, from coming to the Island, or letting him die. For most of the episode, he plans to let him die, but ultimately he's unable to go through with it and saves him.
- Ghost Story: Jin tells one in Korean, and still manages to startle Hurley."And the girl turned to the man who saved her and said, 'Thank God. I was afraid you were the Hook Man.' And the man looked at the girl with a smile and said, 'Don't worry, little girl. My hook is....STILL IN YOUR FATHER'S HEAD!'"
- Parachute in a Tree: Desmond's party find the pilot of the helicopter hanging from a tree by her parachute.
- "The Reason You Suck" Speech: Ruth is having none of it when Desmond tries to justify leaving her a week before their wedding to become a monk."Well, it's a good thing a bloody shepherd didn't help you up, or I suppose you'd be off with the sheep wouldn't you? Next time you want to break up with someone, Des, don't join a monastery. Just tell the girl you're too bloody scared."
- Seinfeldian Conversation: Hurley and Charlie discuss whether Superman or The Flash would win in a race. This is actually plot relevant, since Desmond knows from his vision that this is the cue for Charlie's imminent death.
- Self-Fulfilling Prophecy: Unlike Desmond's previous flashes, this episode's vision only comes true because of the vision itself. Desmond would never have known he needed to head into the jungle to find the parachutist without it, nor would he have specifically gathered the people he saw in the vision.
- Shout-Out: While hiking along the beach, Charlie, Jin, and Hurley whistle "The Colonel Bogey March" from The Bridge on the River Kwai.
- Visual Title Drop: When they find the parachutist's backpack, one of the items inside is a Brazilian edition of Catch-22.
