Jack Sullivan – a Wall Street wonder kicked to the curb
Jack Sullivan is at the top of his game: a relentless Wall Street investment banker celebrating a whale of a deal in a Manhattan strip club, on the verge of a managing partnership and marriage to socialite and PR whiz Melissa. A weekend in the Hamptons on the boss’s yacht nails his promotion – but Monday morning Jack arrives at work, expecting to move into the corner office, and instead finds himself at the center of an insider trade in which he had no part. After turning down hush money, he’s quickly tossed to the curb with a cardboard box, and has to vacate his perk of a fabulous Manhattan loft. Stunned by her fiancé’s sudden lifestyle alteration, Melissa thinks it’s time for a breather. Instead of toasting his success with friends, Jack finds himself buying rounds for strangers in a downtown dive bar. They convince Jack he’s the one who needs the break. Jack wakes up the next morning with a massive hangover, on a plane about to land in Victoria, B.C.,Canada, far, far away from his stellar life. An approaching storm on the eastern seaboard is grounding all aircraft, making a quick return to New York impossible.
Natalie Gregory – a talented but frustrated artist working a day job on the tourist docks
Natalie is returning to Victoria after visiting her sister Maggi, a wedding gown designer and “bride to be”, in New York City. After landing, Natalie rushing to her making-ends-meet job hails a cab. Jack,who, distracted by circumstances and a headache, scoops the taxi. His first impression of Natalie through the taxi window :giving him the finger,and shouting “A**HOLE!”
Real whales and a real woman push Wall Street to the back of Jack’s mind
Jack is stuck in Victoria and looking for distraction. While strolling the harbourfront, he meets the Captain who urges him to go whale watching. This reacquaints him with Natalie, whose daytime job is a whale watching guide. Natalie books him on a tour and while Jack and Natalie are on the boat, emergency strikes. The Captain has a heart attack. Jack takes the helm and handles the boat with ease. He is in his element, and steps off Wall Street’s golden escalator and into the Captain’s shoes, taking up residence in a houseboat on Fisherman’s Wharf. Jack’s attraction towards Natalie grows and soon he’s all but forgotten Melissa, who has already turned her attention to an Argentine polo player. Jack begins dreaming of returning to his grandparents’ home, a ramshackle yellow house overlooking the strait. A preservation order is keeping the house from redevelopment, and it is in foreclosure.
Natalie falls for Jack
Natalie is wary of Jack’s attention, and Jack soon learns why. Her sister ‘s wedding looms and Natalie’s ex Joe will be there. Natalie takes Jack as her buffer, and they embark on a road trip through the Rocky Mountains, to the Canadian prairie for a traditional Ukrainian wedding. During the wedding celebration, Natalie and Jack realize they are in love. Jack tells Natalie that he has to go back to Manhattan the next day, not revealing to Natalie that he’s working on a financing deal to develop his family property and save the ramshackle yellow house. Jack reassures Natalie he is coming back. After he has has left for NYC, Natalie finds out about Jack’s fast life and engagement to Melissa, and decides she’s been betrayed once again.
Jack commits to Victoria and saves his childhood home
Hurt and angry, Natalie returns home to Victoria, and begins to paint again. While nursing her wounds, she receives news that she’s won a prestigious grant to pursue her art. With nothing anchoring her in Victoria, she quits her job and heads for Brooklyn. Jack returns to Victoria excited he’s secured the deal and save his grandparents’ home – but he has no one to share the news with. Natalie does not return his calls. Jack throws himself day and night into the whale watching business and the house deal.
Natalie becomes New York’s new ‘it girl”
Alone after a day on the boat, Jack is sifting through his forwarded mail and receives notice of Natalie’s upcoming show in NYC. He’s missed the art opening, but he’s found Natalie. A few days later, Natalie bounces into the gallery and sees her paintings being packed into crates. A mysterious buyer has purchased them all. In spite of being the toast of New York’s art scene, Natalie discovers that the shine is off the apple, and that she longs for her more simple life in Victoria.
Natalie returns home and Jack is there to greet her
Natalie decides to return home to Victoria, and en route, reads an Op-Ed piece in the New York Times “Why I traded Wall Street whales for whale watching” by Jack Sullivan. With the knowledge that Jack is the real deal, Natalie heads straight from the airport to the Springtide office, where her paintings hang on the walls. The story ends one year later with Natalie and Jack celebrating their elopement with family and friends.