In the book Jake made many, mini trips as a test and his wait for Kennedy was five years instead of three. Eventually he thinks he has it all "Ground Hog Day'd" until the very end with this scene. Jake understands that his is an ultimately sad love story of two people in love forever just out of sync. When Sadie answers yes he knows he can never try again.
When I read the book my first thought every time he came back was TV series. Lets hope they make a few more seasons because in Jake's original book timeline Sadie has a much much much sadder life. Also Jake is already on the wrong side of 30 when he starts and ages normally while Sadie starts each reset in her early 20s. So he knows he has so many trips.
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