Life leading up to The Sims 3
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In The Sims 3, Derek is a teenager living in Sunset Valley with his father, Harold Greenfield. Derek's mother, Jacqueline Greenfield, left him and his father when Derek was a child for unknown reasons. Derek has his eyes on his neighbor, Daesha Ramirez. Daesha finds Derek rude and annoying, but he continues to try and win her over. Derek has short black hair, dark skin, brown eyes, and wears glasses. He wears a maroon T-shirt with a plaid shirt over it with brown shorts and black high-top sneakers.
Life leading up to The Sims 2
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By the time we get to The Sims 2, Derek has succeeded in his attempt to win Daesha over, and they are married and have a daughter, Stephanie. He also has two grandchildren, Quinn and Alicia. Herb is an elder, living in a cozy house in Pleasantview. He is neighbors and best friends with Herb Oldie. His appearance hasn't changed too much, other than the fact that he is now completely bald and wears a red and white polo shirt. His hair was black before it turned gray.