Simon- a friend of Alex's since kindergarten, Simon is a sweet, mellow guy. He owns a costume shop on St. George Street, and dresses up in a different costume each day to advertise for his business. His feelings for Alex have never diminished, even in the ten years she is gone. Despite her resistance, Simon pursues her. But when he discovers the complexity and danger in being a part of her life, he wonders if he's up to the challenge.
Nick- Joe's best friend, Nick is a highly intelligent, awkward, and sweet guy. He has been stuck in the "friend zone" with her for years, but would rather be a part of her life than nothing at all. He is a calm, mellow contrast to Joe's edgy, sarcastic personality. Despite Joe's threats, he bonds with Alex and agrees to help her reconcile with Joe if she in turn helps him. Loyal to the end, Nick gets swept up in the chaos and struggle the Waverly women will face in the days ahead.
Mr. Picolata- , or "Uncle Russell," as the girls call him, is a sweet southern gentleman who has known the Waverly women their whole lives. Russell is always available to offer wisdom and advice. A small-town man and bachelor for life, he owns Picolata farms out by the Intracoastal, and only comes to town to visit the girls and sell his wares at the local farmer's market. Russell's seemingly simple life is turned on it's head as the girls embark on their mission and he ends up becoming more a part of their lives than he ever thought he would be.
Ronan- a sexy, dangerous man from Alex's past, Ronan follows Alex to St. Augustine and is waiting for the right moment to appear. The leader of a secret society seeking to take control of the city, he will stop at nothing to keep Alex from realizing her true potential.
George- When Alex returns and starts working at the Inn, Sam suddenly has more time on her hands and is free to live a life of her own. Enter George, an intensely interesting guy who sweeps Sam off her feet and turns her life upside-down. The other Waverly women don't trust him, but has Sam so captivated that she doesn't care.
Vance- the confident, charming guy Joe meets her first day at Flagler College, Vance is not all he appears to be. He shows up at the right time, says the right thing, and brings an element of adventure and surprise to Joe's life. But is he too good to be true?
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