Ellis Looks Like Sterling Point’s Conrad, but Rory Has Conrad’s Biggest Advantage

Ellis feels like the obvious Conrad of Sterling Point. He is reserved, connected to the summer place and part of a romance that takes time to develop. His relationship with Annie grows through small conversations, shared moments and feelings neither of them understands immediately. By the end of the season, Annie staying on the island makes Ellis look like the clear choice.
The comparison works on the surface, but Ellis is missing the biggest advantage Conrad had with Belly.
Conrad was part of Belly’s life long before their romance began. He knew her as a child, watched her grow up and shared years of family memories with her. Even when Belly tried to move forward, Conrad remained connected to her childhood, Cousins and the person she was before any relationship began. Their past did not guarantee a healthy future, but it made a clean ending almost impossible.

Rory has a similar place in Annie’s life. He knew her before the island, before the family secrets and before her carefully planned future fell apart. He understands the ambitious Annie who expected herself to succeed at everything. He also understands how badly failure can affect a person because he places the same pressure on himself.
Their piano conversation makes the connection clearer. Rory felt so threatened by another musician’s talent that he asked his cousin to break his hand. Annie reacts to failure in a less extreme way, but the fear behind it is familiar. Her rejection from the summer programme does not feel like one disappointing result. It makes her question the entire life she had planned.
Rory understands that reaction because achievement is also tied to his identity. He and Annie can speak about pressure, fear and family problems without needing long explanations. They come from similar lives, carry similar expectations and know what it feels like to lose control of a future that once seemed certain.
Ellis gives Annie something different. He meets her after her old plan has already failed. With him, she can explore a version of herself that is less organised and more open to uncertainty. He is connected to the island, her mother’s past and the life Annie never knew she could have.
However, Ellis has only met Annie during one unusual summer. He has not seen her in New York, dealing with school, pressure or the daily habits that shaped her before Sterling Point. Annie may enjoy becoming a different person on the island, but her ambition and anxiety will not disappear when summer ends. Ellis will eventually need to understand both versions of her.
Rory’s advantage does not make him the better choice. He hides important parts of himself, and Annie catching him playing piano raises a fair question about how honest he has been. Knowing a person for years also means very little if the relationship keeps them trapped in old habits.
Ellis may help Annie build a new life. Rory may understand the life she already survived. Season two can now test which connection works beyond one summer.
Ellis has the slow burn that makes him look like Conrad. Rory has the shared past that made Conrad impossible to forget. The real choice is not only between two boys. Annie must decide whether she feels more understood by the person who knew her before Sterling Point or more herself with the person she met there.