I didn't rush to see Jack Goes Boating during its limited art house release but now I wish I had, and I'm grateful I didn't miss it altogether thanks to the power of Netflix. This is the directorial debut of Philip Seymour Hoffman, who leads a wonderful cast that includes Amy Ryan and John Ortiz. Hoffman plays Jack, a limo driver who aspires to raise his economic stature by landing a job as a driver for the New York Metropolitan Transit Authority. He doesn't expect a lot from life and life has certainly obliged him to this point, but then his best friend, Clyde (played by Ortiz), sets him up on a blind date with his wife's new coworker, Connie.
Jack and Connie are not the prettiest couple around, but the two of them hit it off and embark on a relationship that stretches them both out of their comfort zones. What makes the story so touching is the lengths Jack goes to express his love for Connie, reminding me of my all-time favorite line from another romantic comedy about less-than-perfect lovers: "You make me want to be a better man" (Jack Nicholson to Helen Hunt in As Good as It Gets). Jack goes out of his way to learn to cook and conquer his fear of water by learning to swim so he can take Connie boating.
The transformative power of love turns Jack and Connie into better, more fulfilled human beings, while the lack of it sends Clyde's marriage into a tailspin at the same time. This is a film about love at its best--freely given and unconditional. Jack is no more a wealthy prince than Connie is a beautiful princess, but they teach us by example that real love between two people is less a socioeconomic arrangement or solution to personal insecurity, and much more about being our best selves and supporting those we love. I'll take that over a fairy tale ending any day.