Chris Eigemann plays Jake Singer, a well-liked middle-aged English professor to a group of privileged students at a posh high school for precocious young white men with floppy hair styles and ironic disdain, located somewhere in New York City. Having just discovered that his ex-girlfriend is engaged, Singer begins a psychoanalytic treatment with an Argentinian analyst, played with relatively understated gusto by Ian Holm. Singer meets Allegra Marshall (Famke Janssen), a woman whose deceased husband was a benefactor of the school; she is now the single (and rich) mother of two adopted children.
They fall in love, complicated slightly by Singer's father, a curmudgeonly heart surgeon, and a rather strange plot contrivance involving Marshall's failure to tell the adoption agency that her husband had died even though the biological mother had insisted that the child go to a family with a mother and a father. In one other plotline, left satisfyingly unresolved, Singer has clearly been the mentor to a young African American student, who self-sabotages at this otherwise all-white, all-privileged academy.