Jump Cut by Ted Staunton
This is the third book in Seven, The Series (previous books are Between Heaven and Earth and Lost Cause). Each book follows one of the seven grandsons who have been tasked with an assignment in their grandfather's will.
Here we have Spencer, who is off to Humber College in the coming fall to study film. He is a huge movie fan, and often imagines the world around him in filmography terms. He has been given a seemingly simple assignment. Find the aging movie star Gloria Lorraine and film himself getting kissed by her. He is given the money for a good camera and any travel that may be required. There is also a backup assignment if Gloria Lorraine should no longer be living. Spencer easily finds information on Gloria Lorraine on the Internet and his mother remembers her father's love of the actress when she was growing up. He finds her on Facebook and sends her a message, finding her in a seniors' home in Buffalo, not far away at all. This ease makes him feel a little resentful of the larger travel undertaken by his cousins, but he is determined to follow through and get the kiss.
However Gloria Lorraine has other plans. She tells him they have some errands they need to run before she will give him the kiss, and Spencer's adventure begins. With shady characters, guns, and drugs, Gloria's errands take them back into Canada and into northern Ontario on a journey into the past. Oh, and did I mention Gloria's film-loving granddaughter is along for the ride?
Spencer is a nice young man that knows he isn't the macho type that most girls like, but he cares about his family, and keeps his promises, and he thinks on his feet too.
Sounds like a curious assignment.
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