The story begins with four aspiring writers, (all in their 20s, acquainted with each other and living in New York City
) who have just hired world renowned writer, editor and teacher Leonard for a 10 week seminar to teach them how to be better writers and help their careers along. And they have absolutely no idea
what they've gotten themselves into.
You see, Leonard is a world-weary misanthrope who cannot and will not tell a lie or go along with polite social facades. Leonard only respects the written word, (when it's done right) and that unique synthesis of inspiration, drive, and energy that makes a story come alive, turns its characters into people, and its settings into places that seize the imagination. He certainly has no use for things like your feelings, need to be supported, or your idea of what is politically correct and what is out of bounds.
The foursome are quickly challenged on everything from writing bloodless, soulless stories that only exist to amuse themselves with their own wittiness to being over privileged, entitled kids with delusions of grandeur. It's not just their stories being examined, (and usually torn apart) it's who they are, how they identify themselves, and how they perceive and interact with the world.
As the weeks go by and the seminar continues, all of the resentments, attractions, lusts, anger, untapped talent and various other dramas that the four would-be writers hide just under the surface start boiling over, leading to multiple confrontations...
The four writers are:
- Douglas: the nephew of a well known writer and hailing from an upper class family, his chief publications thus far have been pieces for The New Yorker and similar magazines. He insists however that he is "a writer of fiction" and to prove it he frequently goes on writer's retreats to top notch writing colonies, which he mostly gets into because of his last name. Has a talent for describing scenery and conveying images, but otherwise his writing tends to be either a bland retread of things that have come before, or centered around utterly banal ideas. Leonard identifies him as "a literary whore" getting by on his name and connections. He very much wants to get Izzy in the sack.
- Izzy: The most sexually free and rebellious of the four, Izzy's stories (and personal life) are essentially Sex, Drugs and Rock & Roll, with writing substituted for rock & roll. Hot, Really Gets Around, and is generally lusted after by all. She freely admits that ultimately her stories don't mean all that much to her and that she's Only in It for the Money. Thus she's always looking for ways to cash in, and is quick to think of angles that could turn a story or her own personal narrative into an appearance on a daytime talk show or media grabbing headline. She wants to use Douglas for his connections and has a slight soft spot for Martin, who she attempts to help (as she sees it anyway) on occasion.
- Kate: A child of an Old Money family, most of the action of the play including the seminars with Leonard take place in Kate's (rent controlled) apartment. Kate went to school with Martin, where their mutual interest in writing and stories drew them together, despite their very different backgrounds. Kate's main work through much of the play is a story that is her ode to Pride and Prejudice which she's been rewriting for 6 years due to encouragement by various teacher and critics, (most if not all of whom were Damning With Faint Praise) and which makes Leonard want to gag after reading the first sentence. She's a liberal, feminist, and occasionally comes off as unthinkingly harsh toward others and somewhat unaware of how privileged her life is. She secretly has a thing for Martin, although she will never admit it.
- Martin: A painfully shy and socially awkward wallflower who cannot bear to have his stories read by anyone. Martin is in many ways the odd one out in the group; he's more or less the only one truly Doing It for the Art, he disagrees with the others who mostly plan to use this seminar as a career stepping stone, and he's by far the poorest. In fact, the $5,000 he paid into the seminar leaves him in danger of being kicked out of his apartment because he can't pay the rent without it. He hides a barely repressed anger aimed at both the world in general and specific people (especially Douglas) behind his shy exterior. He also thinks that he's morally superior to everyone else due to being poorer and true to a made-up and rather arbitrary code of what an authentic artist is. Leonard derisively calls him "a pussy", and towards the end of the play, Leonard amends that, with much greater respect to "a Talented Nobody". He is hopelessly in lust with Izzy, despises Douglas, and has idealized Kate since high school.
This play contains examples of:
- Attention Whore/It's All About Me: Kate accuses both Martin and Leonard of this.
Boys, boys, boys—you just never get enough of yourselves, do you?
- Be Careful What You Wish For: Everyone in this play, more or less. There's also a specific case of dialog where Douglas submits a story, Leonard finds little things here and there to praise, and Douglas is actually Genre Blind enough to say "I'd like some criticism." Leonard's response is to look at him and say "Oh, would you now?"
- Betty and Veronica: In a way, Kate and Izzy are this for Martin.
- Break the Haughty: Kate, although she takes it as a much needed wake-up call. In a way, it also happens to Martin, and Leonard is in the midst of a prolonged one that has dogged him for years as well. For example, Leonard considers his past jobs as an editor and professor to be "servant's work" that is beneath him, and he hates that he has been given certain positions out of pity, but he was also in dire enough straits that he was forced to accept them.
- Brutal Honesty: Leonard, all the time. Even about himself, in the end. An an example, here he discusses his conclusions about the narrator of Kate's story:
I know who your narrator is. She's an over-educated, completely inexperienced, sexually inadequate girl who has rich parents who give her everything. She's got nothing to say so she sits around and thinks of Jane Austen all day. I don't give a shit about her.
- This is also a key source of the play's humor in general.
- Can Not Spit It Out: Martin and Kate, towards each other.
- Can Not Tell A Lie: Leonard actually does try the whole being polite and Damning With Faint Praise routine at one point, and is barely able to keep it up for even a few minutes. He looks physically relieved when he can go right back to Brutal Honesty again.
- Character Development: Kate probably gets the most. She starts off as prickly, defensive, totally inexperienced character who has been stuck on the same concepts and in the same ruts for years, she learns to move on, mature, and starts going out to get some real life experience under her belt.
- Character Filibuster: Leonard closes the last seminar with an impressive one.
- Comfort Food: The first seminar drives Kate into a wild binge that includes uncooked cookie dough, ice cream and potato chips.
- Cynical Mentor: Leonard is this for the most part, but when he encounters work that is actually good and shows talent and drive his own enthusiasm comes out.
- Deal with the Devil: Leonard calls his offer to Martin to help Martin's career and be Martin's editor this.
- Did Not Get the Girl: Martin winds up with neither Kate or Izzy in the end.
- Dirty Old Man: Leonard sleeps with both Izzy and Kate, and his speech reveals that he slept with plenty of students when he was a professor.
- The Ditz: Although it's easy to peg Izzy for this trope, it's really Douglas who winds up fitting this role best.
- Doing It for the Art: Martin voices the belief that every page of creative writing is sacred and criticizes all of the others for plans to cash in or act in ways he considers to be dishonest as creators.
- Douglas is surprisingly distressed and sincere when, after Leonard calls him a whore who should write in Hollywood because they would give him endless scripts to write based on his last name, he protests "But I'm a fiction writer. A novelist".
- Don't You Dare Pity Me!: Multiple characters have shades of this. Leonard is probably the strongest case, most notably in his monologue that reveals a lot about his life and history in the last seminar.
- Establishing Character Moment
- Douglas begins the play with a glowing review of the scenery of his latest writer's retreat and comparing it to others he's been on. The way he does it both establishes his talent at conveying imagery and that he's a totally nonsensical, pretentious and shallow goof.
- Martin goes on a bitter, venom laced tirade at Douglas' description of the writer's retreat when Douglas leaves the room, but doesn't dare say it to his face.
- Izzy does an extended breast flash in the opening minutes for no reason other than a whim. (And maybe to tantalize Martin).
- The Ghost: Luis, a friend of Kate's from her college days who has a story about his life as a cross dressing gang leader that actually impresses Leonard. Because he doesn't exist, and the story is a new one Kate wrote.
- The Gift: Martin has it. Leonard has it too, and immediately recognizes it when Martin finally gives him something to read.
- Green-Eyed Monster: One of Martin's defining traits. He is endlessly bitter and jealous about the fact that he's surrounded by people who seem to have it easier than he does, es when it comes to money and material comfort.
- The Hedonist: Izzy.
- I Just Want My Beloved to Be Happy: Kate tries to do this when Martin and Izzy hook up, but the fact they're getting it on right in front of her in the apartment where she let Martin stay quickly becomes too much for her.
- Jade-Colored Glasses: Leonard certainly wears them.
- Jerkass Façade: Leonard is paradoxically a true JERK and incredibly sensitive, burnt out, and used up by life. The facade is his defense mechanism.
- Jerk Witha Heart Of Gold: Leonard. For all the harm he does to the four, he does equal good, and does move their careers forward and challenge them to grow.
- The Lad-ette: Izzy, in many ways.
- Lust Object: Izzy.
- Man Child: Martin is presumably at least in his mid 20s, but often acts more like an angry, spiteful teenager.
- Never Live It Down: Leonard's plagiarism is an In-Universe example. His reaction when the four of them bring it up:
That was 32 years ago!
- No Social Skills: Martin. Spelled out towards the end by Kate.
You don't know anything about people. People are complex. Life is complicated. If you don't get this you'll never be a real writer.
- Not So Different: Leonard lays out the miserable path that Martin is setting for himself, quickly making it clear that it's the same path that Leonard himself has journeyed.
- Obfuscating Stupidity: Don't underestimate Izzy's determination, political skills, or brains just because of her personal life.
- Oblivious to Love: Martin has no clue that Kate likes him as more than Just Friends.
- The Resenter: Martin, particularly to Douglas.
- Shrinking Violet: Martin paid $5,000 that he couldn't afford to pay to get into this seminar, and then is too pathologically shy to submit his stories for review.
- Skilled, but Naïve: Martin.
- Sleeps with Everyone but You: As far as Douglas is concerned, Izzy is this.
- Small Name, Big Ego: Douglas, who on several occasions trashes true literary superstars that have accomplished something while bragging about his own (rather modest) talents.
- Starving Artist: Martin.
- Taught by Experience: Leonard thoroughly encourages his students to get out of the house, take chances, put themselves at risk and experience everything, including the bad of the world. That, he feels, is what gives a writer something worth saying.
- Teacher/Student Romance: Both Izzy and Kate sleep with Leonard before the end of the show, and it's not exactly something he's shied away from in the past either.
- Tsundere: Kate has most of the qualities down pat.
- Twice Shy: Kate and Martin.
- Who's Laughing Now?: Kate is delighted when Leonard lavishes praise on a story from her college friend Luis. Because it's really a new story Kate has churned out in a couple of days. She loves that she has put one over on him and it lifts her self esteem right back up after Leonard had crushed it before. That said, it's strongly hinted that Leonard knows about the deception and that Kate is the writer.
- Who Writes This Crap?!: Leonard does this to Kate's story in two different seminars.
- Wide-Eyed Idealist: Martin refuses to believe that Izzy has her own ulterior motive for things like sleeping with Leonard, believes her Blatant Lies, and falls into a very childish and facile pattern of viewing the world: anyone he admires is a wonderfully good person full of Incorruptible Pure Pureness, anyone he dislikes is an irredeemable, despicable prick.