Miles is a writer. (The backward "Write now" chest tattoo clues you into that.) He's struggling with relationship issues, specifically his latest breakup with the winsome, willowy Julia (Jen McPherson).
Though he initiated the split, he misses her, calls incessantly, shows up uninvited and inevitably, eventually talks his way back into the relationship. Will it work out? Who knows, and frankly, who cares? It's not clear that even Miles has a strong feeling either way. He fears he's a jerk, and maybe if this works out, he just might not be. Rose, as a filmmaker, surrounds Miles with a coterie of women to assure him (and us) that he's not a jerk, and one wonders just whom he is trying to convince.
"Miles to Go" can't pull off an update of the urbane relationship dramedy in the vein of "Manhattan" or "Annie Hall" for a couple of reasons. There's an undeniable tone deafness in the casual hipster misogyny (vulgar, pointless sex talk) and racism (a cringe-worthy "gangsta rap") that permeates the film, which doesn't help to endear the polarizing protagonist. But what really hampers "Miles to Go" is its aimless wandering. Many things could be forgiven with some growth or movement in the journey, but ultimately, this one just ends up running in circles.
"Miles to Go."
MPAA rating: None.
Running time: 1 hour, 25 minutes.