Since Sterling Point became the latest breakout young adult drama series on Prime Video this summer, no one has been able to stop thinking or talking about what's going to happen next. The show's success led the streaming service to quickly green light a second season, ensuring we will be back in Muskoka for another round of family and relationship drama.
Naturally, we already have a wish list of what we want to see in Sterling Point season 2 and creator Megan Park has already offered some early teases about what to expect from the follow-up season. Based on Park's insight and the cliffhanger involving Annie and Connor's birth mother, there's a perfect way to combine this casting with a special The Secret Life of the American Teenager reunion.
Shailene Woodley should guest star in Sterling Point season 2
In case you have forgotten, Sterling Point creator Megan Park had her career breakthrough starring as Grace Bowman in the ABC Family teen drama series The Secret Life of the American Teenager alongside Shailene Woodley. The stars have built a lasting friendship outside of the series and have collaborated with Park's feature directorial debut The Fallout.
While you might be thinking that Woodley, who's currently 34 years old, might be a little too young to play the birth mother of 18-year-old twins Annie and Connor (played by Ella Rubin and Keen Ruffalo, both 25 years old), where there's a will, there's always movie magic. There's only 10 years in between the newly minted Emmy Award-winning actress and the Sterling Point stars, but it would work.
Sterling Point didn't reveal anything about Annie and Connor's birth parents and they don't have much knowledge on the parents that gave them up for adoption. However, in the season finale, Connor goes behind his twin sister's back and pursues contact with their biological mother. Annie doesn't share that desire, especially with their lives already overrun with revelations.
It's unclear under what circumstances Annie and Connor were given up for adoption to Steven and Goldie, but Woodley made her breakthrough playing a teen mom in a teen drama series. Coming back together with her best friend and former co-star would bring them full circle in a way thought would make The Secret Life of the American Teenager fans especially nostalgic.
In order to play Annie and Connor's birth mother, Woodley's character would have had to had them as a teenager to make the age difference work. Still, the 10-year gap between the stars would have to be suspended by disbelief and the magic of makeup. But you can't deny that Rubin and Woodley share a striking resemblance and would undoubtedly have an excellent on-screen chemistry.
Woodley has been in the news lately for a major career achievement. After landing her first Emmy Award nomination for HBO's Big Little Lies in 2017, she took home her first win in 2026 for her memorable guest role in the second season of Hulu's Paradise. She was previously nominated for a Golden Globe in 2011 for her breakout film role in The Descendants.
The talented actress' Emmy win comes ahead of her upcoming role in Hulu's limited series Count My Lies, which also stars Lindsay Lohan and Kit Harington, but with no other major television roles currently lined up, she has an another chance to collaborate with Park and bring an exciting and surely complicated character to life. Even if it's not that character, she needs to be in Sterling Point.
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