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Sam also knows about Lilith thanks to Ruby's intel, but he doesn't tell Dean.When her plan is denied, she leaves saying she doesn't want to watch them lose.
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The full extent of Ruby's motivation to help the Winchesters and become involved with Sam is not revealed until the end of Season 4 when the scope of her manipulation and deceit is revealed.
Following Dean's incarceration in Hell, their relationship took a big leap forward as they began to get physically intimate.
Meanwhile, Dean goes the local bar, The Cobalt Room, where he meets the sexy and independent Lydia and they have one night stand in her house.
On the next morning, Dean goes to Lydia's place to get Bobby's flask that he forgot there and he witnesses Lydia talking to her baby daughter Emma. Meanwhile Sam discovers that the symbol is relative to Amazon warriors and they can reproduce in 36 hours.
Soon Dean receives Emma in his room and learns that she is his daughter while Sam finds that all the victims were killed by their own daughters.