Grim and gloomy, Woody Allen's film is a noirish character study by Woody Allen, not a comedy and not for kids. Chris's slide into the standard soul-sucking vortex is not especially affecting. His thudding caddishness, lacking in conscience or compassion, makes his appeal to Chloe, who otherwise seems self-confident to a fault, seem odd, except for the fact that she's preoccupied with having a baby, that recurrent bane of Allen's women.
Because Chris is the indecisive, unhappy protagonist in a Woody Allen movie, you can pretty much guess what happens to him. Though Chris begins by asserting his faith in luck, he ends up adrift and haunted, without any "measure of hope for the possibility of meaning." Maybe it's just luck that the women around him -- irrational, demanding, and voluble -- come to represent that lack.