"As we soon discover, when the lighting shifts on Wilson Chin's excellent re-creation of Flanagan's book-lined office, this has been an imagined monologue; one that Flanagan would never actually utter, but meant to give the audience a clue into his inner fire."

– Brian Scott Lipton, theatermania.com

"The piece has been fluidly staged by Michael John Garcés, using Wilson Chin's library set ingeniously to fit the various locales."

– Michael Feingold, The Village Voice

"Wilson Chin's set for The Dear Boy arrested my attention as soon as I took my seat in the theatre. First of all, its walls are lined with books, hundreds of them, and I love books: I could make out several volumes of the Durants' world history series, Joan Peyser's Leonard Bernstein biography and something with the tantalizing title Moo. Second of all, as I studied it, I realized that it couldn't possibly represent only one room; and as Dan O'Brien's play progressed, I was proved correct: it's actually three rooms, shown to us simultaneously—a teacher's office (table and chairs at dead center), a bar or other sort of party room (open areas at the perimeter of the stage), and a sublet apartment belonging to two poets (hence all the books)."

– Martin Denton, nytheatre.com