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Dean protects her until the moment Uriel threaten Sam. Whenever Anna pops in, Dean is surprised to see her, but treats her kindly, even going so far as to compliment her appearance on one such occasion. They were on friendly terms until Anna goes back in time to kill Mary and John so that Sam could never born. Dean later witnesses her death at the hands of Michael. Dean first met Cassie in Athens, Ohio, where she was at college and he was on a hunting mission. Best looking women over 60. They dated a few times and became close enough for Dean to trust her with his biggest secret - what he did for a living.
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Alex wants children, Maggie is dead set against it, and encounters with new supporting player Sam's daughter Ruby crystallized the fact that the elder Danvers sister was unwilling to budge on the matter. Fans who were hoping that the unhappy resolution might warrant an episode unto itself to commemorate what it meant for the series will be almost certainly disappointed to discover that the hashing-out of all this still happens in the margins of an otherwise standard Supergirl story. 'Damage' was mainly dedicated to long-term plot maintenance like reminding us about Lena Luthor's family-history hangups, giving her, Sam and Kara bonding time, and hanging a lampshade on the silly-even-for- Supergirl 'atmospheric lead bomb' plot device from the end of season 2.
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When Lisa starts to go on dates, Ben tricks Dean into coming back to try to get them back together and is upset when they don't. Ben tells Dean that he is abandoning his family by leaving them, showing that he probably sees Dean as a father. Dean does leave again, but is upset by the state he left Ben in, telling Sam that he left Ben heartbroken. When arrive to kidnap him and his mother, Ben quickly calls Dean who becomes obsessed with rescuing them. During the rescue, Dean hesitates to do anything when the demon-possessed Lisa uses Ben as a hostage, but manages to free him by throwing holy water in her face. Dean also tells Ben to ignore the demon's taunts that Lisa doesn't love him. Despite this, Dean nearly suffered from a taunt when the demon said he was Ben's real father before stating Lisa doesn't even know.