A mutually dependent relationship unfolds between Leonard Schiller (Frank Langella), an old-school writer of the Bellow-Roth-Howe generation of realists, and Heather (Six Feet Under's Lauren Ambrose), the eager-beaver Brown University grad who worms her way into Leonard's life and tries to convince him that her forthcoming master's thesis on his work will put a new shine on the old man's dusty reputation.
When Heather, a thief in more ways than one, bursts in on Leonard's cramped, poorly lit Manhattan apartment with her long red hair and chipmunk cheeks, the long-widowed writer is putting the finishing touches to a manuscript 10 years in the making that no hip publisher will even look at. Langella is superb, at once held-in and intensely physical in his rendition of this proudly anachronistic man, a shell imprisoned in his impressive bulk and formal suit, with only the slightly hunted look in his otherwise blank eyes revealing a fear that his day may be done.
Starting Out in the Evening is about people who are just ticking over, not only Leonard but his devoted, equally becalmed daughter Ariel (Lili Taylor), whom he loves but distractedly holds at arm's length. A former dancer and Pilates instructor whose biological clock keeps murmuring "pushing 40," Ariel is girlish and eager to please in the awkward way of women who have fallen behind in the business of finding an adult identity to grow into. (She tiptoes in and out of her dad's apartment bearing soup.) Her lack of self-definition also makes her both a victim and an exploiter of poorly chosen men, notably a similarly under-evolved former boyfriend (Adrian Lester) whose re-entry into Ariel's life earns the reflexive disapproval of her father, even as he succumbs to the blandishments of a woman less than half his age.
Like Heather, Wagner went to Brown, and his grasp of the clash between old and new academe is witty and quietly assured. But if there's little question about whose side he and Morton are on, neither world gets off lightly, or without sympathy. Callow, ambitious, and raring to connect the dots between what she thinks she knows about Leonard's life and his art (the movie takes a discreet swipe at dirt-driven magazine writing in the form of a canny Village Voice editor nicely underplayed by Jessica Hecht), Heather is a parasite. But she's a useful one, because Leonard, with his fastidious — and, did he but know it, terrified — withdrawal from the world, is the embodiment of snooty ivory-tower detachment. Heather may not know as much as she thinks about Leonard's life, but she galvanizes him, albeit with a high cost to them both.
If Starting Out is a movie about how little we know and how much we presume, it is also about transformation, about heartbreak and halting renewal. There's no vulgar equivalence between Leonard and Heather, and when it comes down to it, Starting Out in the Evening comes down squarely on the side of the old-fashioned literary life. Yet if Leonard may be kept going (and kept out of print) by "the madness of art," he can't proceed without the painful recognition that, as he ruefully puts it, his characters haven't been doing anything interesting. He's always known that the unexamined life is not worth living. Heather may be an intellectual and emotional thief, but she has forcefully awakened Leonard to the fact that the unlived life may not be worth examining.