After breaking up with his girlfriend of seven years, late-20s assistant book editor Doug (Brian Geraghty) decides to go on an adventure: he and his stock trader friend Mitch (Chris Marquette) will trek to the summit of Mount Kilimanjaro. But his asshole boss (Jim Gaffigan) is not about to give him a vacation, his busybody parents are crowing about “irresponsible purchases,” his ex keeps coming back for dinner and snuggles, and he meets an awesome new girl (Abigail Spencer) on his daily run. Will he tell his boss to fuck off, shed the affections of his ex, tearfully explain to his parents that he’s gotta live his life, and set off to Kilimanjaro with his new girlfriend in tow?
The answer to most of those questions turns out to be “no,” which is part of why Kilimanjaro is such a wonderful surprise. In his feature film debut, Walter Strafford snuck a smart and tricky movie about disappointment into the shell of a formulaic rom-com about chasing your dreams. So many films traffic in wish-fulfillment that it’s hugely gratifying to see one that has some of the same conventional rhythms but that also acknowledges that sometimes circumstances refuse to cooperate with one’s fantasies and grand plans. Kilimanjaro is funny and breezily enjoyable, but it also works to undermine clichés at every turn, ending up not on a mountain, but somewhere poignant and unexpected.
— Eugene Novikov