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BiographyNOTE: This biography contains spoilers!
Anna Stern is the daughter of Cameron Stern and Patricia Stern. She moved from Pittsburgh to Newport and makes her first appearance in the fourth episode of the first season, The Debut. She teaches Ryan how to waltz before the big night of Cotillion, the evening the girls make their debut into Newport society. When Ryan ditches her at the last minute before Cotillion, Seth (after being dumped by Summer) has a chat with her. They go to the Cotillion together, and Summer ends up not having a date.
She finally returns in episode 9, the first day back at school. Anna is going to attend Harbor Private School along with Seth and the gang. During the summer holidays, Anna has sailed to Tahiti. When she meets Seth again at school, he asks her if she can help him make Summer like him. Anna's reluctant to do so, and you can already she she likes him. When she kisses him at the carnival, he asks if it was "all part of the plan?". Not wanting Seth to know how she feels, she lies and says yes. Seth has also traded his tickets into a prize, and gives Anna a cute teddybear. In episode 10, Anna and Seth argue about Summer. All Seth ever does is talk about her. So to apologize, he invites Anna to a charity event on a yatch, and she accepts. When she tries to kiss him, he tells her that he's thirsty.
It's Thanksgiving dinner at the Cohen's, and Anna is invited. However, Seth gets an unexpected visit from Summer; he kisses both the girls and they find out. While Anna is up in his room, playing Jenga against Captain Oats, he's kissing Summer in the pool house. When he tells Summer he needs to check on the food, he's kissing Anna in his room.
After the big letdown at Thanksgiving, Summer and Anna become friends. They're hanging out with eachother, studying for tests, ignoring Seth and even flossing their teeth together. When Seth apologizes to the girls, she realises how much she actually likes him, and asks him out.
Seth has to choose between Summer or Anna. After the Christmas party, where Summer dressed up as Wonder Woman and Anna drew him a comic book, they tell him he can't have both. And neither of them wants to be just friends with him. On New Year's Eve, Summer tells Anna to go find someone to kiss. So Anna goes to Seth. He chooses her, and they're now a couple. Only, Summer doesn't know.
After telling Summer they're dating, Anna and Seth are officially a couple. They've been invited to Palm Springs by Oliver, and are looking forward to a couple-y weekend in their own room. But things don't turn out the way they planned. Summer barges into their room uninvited, telling them they're just like brother and sister.
Summer's comic book education begins, and Seth is ignoring Anna. When Summer finally leaves, he starts talking to Anna. When Anna confronts him about what happened earlier, he says "Anna, you know how excited I get turning people into comics!" Anna says "I know how excited you get turning Summer on, yeah." And after an incident with Marissa, the first thing Seth decides to do is call Summer, Anna's had enough. Finally, she breaks up with him, realising she's not the one he really wants.
Being the great person she is, Anna doesn't hold a grudge. In the 20th episode, The Telenovela, Summer is ignoring Seth. Anna (with all her sage wisdom) comes to the rescue and finds out why she won't talk to him in public. She then watches Seth declare her eternal love for Summer, just a few weeks after she broke up with him.
After breaking up with Seth, Anna decides it's time for her to leave Newport and go back to Pittsburgh. Seth thinks it's because of him, but Anna insists that it's not. Anna says that she misses the seasons, the fall foliage, the snow, the first signs of spring. When Anna comes to say goodbye, she gives Ryan a letter she wrote for Seth and leaves. It was too hard to say goodbye. Seth rushes to the airport to find her, he doesn't want her to leave because of him. When she walks away, she has the little teddybear Seth gave to her in The Heights in her backpack.
It's been two years since Anna and Seth have seen each other, but when Seth goes to Brown to win Summer back, they run into each other. Seth asks Anna for help after telling her the truth about him not getting into Brown. In the next episode, Anna flies to Newport to help Seth get Summer back, and goes with him to the Prom after Summer rejects him. She makes him realise that he has to tell her the truth, and that Seth didn't go to Brown to be with Anna.