After breaking up with his girlfriend of seven years, late-20s assistant book editor Doug decides to go on an adventure with his stock trader friend Mitch. They decide to trek to the summit of Mount Kilimanjaro. Things don't go as planned when his boss denies him a vacation, his parents lecture him, and his ex keeps hounding him. One day he meets a fabulous girl while on his daily run and they instantly hit off. Will he overcome all his hurdles and set off to Kilimanjaro with his new girlfriend in tow?