Flashback # 1:

The camera pans to the left and dissolves into a flashback that Don has begun to narrate - moving backward three years in time to when Birnam was already deeply gripped by the powerful urge to drink. After checking his plain raincoat (with a bottle stashed in a side pocket) at the opera house, the operatic singers abandon themselves as they perform the drinking song, "Libiamo." Don focuses in on the tempting champagne glasses being served, toasted and raised to the joyous performers' lips. He licks his own chops to taste the bubbly, and hallucinates that the singers are actually multiple visions of his own raincoat with a bottle of rye whiskey tucked inside.

Thirsting unbearably for a drink, he squirms and increasingly shows discomfiture in his chair. As soon as he can - during the number's applause, he excuses himself and hurries to retrieve his coat from the check room. The claim check for his overcoat (with his precious supply of booze) has been mixed up with someone else's coat (Helen's leopard coat) and he must impatiently wait until the program is over to find his own raincoat. He and Helen meet for the first time after everyone else has left - she learns how abusive, rude and self-centered he can be:

Don: Goodbye.
Helen: Oh, oh, just a minute. (She holds out his derby hat. He takes it from her and begins walking off.) My umbrella, if you don't mind?
Don: Catch. (He abruptly tosses it in her general direction and it falls on the floor at her feet.)
Helen: (coldly) Thank you very much.
Don: (snarling) I'm terribly sorry. (He picks up her umbrella.)
Helen: You're the rudest person I've ever seen. What's the matter with you?
Don: Oh, just rude, I guess.
Helen: Really, somebody should talk to your mother.
Don: They've tried, Miss St. John.
Helen: My name's not St. John.
Don: St. Joseph, then.
Helen: St. James.
Don: First name Hilda or Helen or Harriett maybe?
Helen: Helen.
Don: All right, Helen.

He had tried to guess her name from her initials on the label inside her coat, bought in her hometown of Toledo, Ohio. She becomes gracious and forgiving to him as they exchange chit-chat about their occupations - she has a job as an editorial researcher at Time Magazine. He is an aspiring, but failed writer - with writer's block:

Don: I'm a writer. I just started a novel. As a matter of fact, I've started several but I never seem to finish one.
Helen: Well, in that case, why don't you write short stories?
Don: Oh, I have some of those - first paragraphs. And there's one half of the opening scene of a play which takes place in the leaning tower of Pisa that attempts to explain why it leans and why all sensible buildings should lean.
Helen: (smiling broadly) They'll love that in Toledo.

He first declines her invitation to "an extremely crazy party" on Washington Square. But when his bottle of rye whiskey accidentally falls from his pocket and smashes on the sidewalk, he reconsiders her invitation to the "cocktail party." The film returns to Nat's bar after a dissolve.

End of Flashback # 1

Still drinking, Birnam beguiles Nat with his intelligent tale of romance with Helen:

That's what's gonna be so hard to write. Love is the hardest thing in the world to write about. It's so simple. You've gotta catch it through details, like the early morning sunlight hitting the gray tin of the rose garden in front of her house, the ringing of a telephone that sounds like Beethoven's Pastorale, a letter scribbled on her office stationary that you carry around in your pocket because it smells like all the lilacs in Ohio....He thinks he's cured. If he could only get a job now, they could be married and that's that. But it's not, Nat, not quite. Because one day, one terrible day...you see, this girl's been writing to her people in Toledo. They want to meet the young man. So they come to New York. They stay at the Hotel Manhattan. Their very first day, she's to introduce him to her parents, one o'clock, in the lobby of the hotel...

Flashback # 2:

Following his third-person narration, another flashback is signaled when the camera pans left and dissolves back in time. In the hotel's lobby, an insecure Birnam loses self-confidence as he overhears Helen's parents (Lewis R. Russell and Lillian Fontaine - actress Joan Fontaine's mother in her first film role) speaking about their only daughter's ne'er-do-well, 33 year-old beau with "no job" who never graduated from Cornell University: "A writer. What did he write? I never heard his name." He avoids meeting and facing up to Helen's "respectable" parents, fearful of revealing his life's weaknesses. He returns to his apartment, sinks lower with more accursed drinks, and confesses to his brother:

I couldn't face it...I couldn't face 'em, Wick, and all the questions they'd ask. I just couldn't do it, not cold. I had to have a drink first, just one - only the one didn't do anything to me.

In a pathetic attempt to keep secret his brother's symptomatic state, Wick conceals his brother's absence (and closet drinking) by lying to Helen when she comes looking for him at their apartment. He explains that Don was probably detained while job-hunting in Philadelphia at the Inquirer. He even takes his brother's place - admitting to having a personal problem with drinking: "You might as well hear the family scandal. I drink. Don thinks I drink too much. I had to promise him to go on the wagon." But Don, who has been hiding in the bedroom, can't let Helen go without hearing the truth: "Thanks very much for your Philadelphia story, Wick, nice try." Helen is again overly-forgiving ("People drink a little. A lot of them get tight once in a while"), but Don is brutally honest about his own addiction:

Sure, the lucky ones who can take it or leave it. But then there are the ones who can't take it and can't leave it either. What I'm trying to say is, 'I'm not a drinker - I'm a drunk.' They ought to put me away once.

Helen naively looks beyond his "not too pleasant" deficiencies, vowing that "the right doctor" could find a cure. Don relates how his authoring brilliance during his college years was soon blocked and tarnished, declining after age nineteen with a recourse to the bottle. He is helplessly schizophrenic, divided between Don the Drunk and Don the Writer. He describes the soaring, creative juices that flow with just a few drinks, and how he spirals down into despair and agony when the booze wears off:

Helen: ...they could be worse. After all, you're not an embezzler or a murderer. You drink too much and that's not fatal...There must be a reason why you drink, Don. The right doctor could find it.
Don: Look, I'm way ahead of the right doctor. I know the reason. The reason is me - what I am, or rather what I'm not. What I wanted to become and didn't.
Helen: What is it you wanna be so much that you're not?
Don: A writer. Silly, isn't it? You know, in college, I passed for a genius. They couldn't get out the college magazine without one of my stories. Boy, was I hot! Hemingway stuff. I reached my peak when I was nineteen. Sold a piece to The Atlantic Monthly, reprinted in the Reader's Digest. Who wants to stay in college when he's Hemingway? My mother bought me a brand-new typewriter. And I moved right in on New York. Well, the first thing I wrote, that didn't quite come off. And the second, I dropped. The public wasn't ready for that one. I started a third and a fourth. Only by then, somebody began to look over my shoulder and whisper in a thin, clear voice like the E string on a violin. 'Don Birnam,' he'd whisper, 'It's not good enough, not that way. How about a couple of drinks just to set it on its feet, huh?' So I had a couple. Oh, what a great idea that was! That made all the difference. Suddenly, I could see the whole thing. The tragic sweep of the great novel beautifully proportioned. But before I could really grab it and throw it down on paper, the drinks would wear off and everything would be gone like a mirage. Then there was despair, and I'd drink to counter-balance despair. And then one to counter-balance the counter-balance. And I'd sit in front of that typewriter trying to squeeze out one page that was half-way decent. And that guy would pop up again... The other Don Birnam. There are two of us, you know. Don the Drunk and Don the Writer. And the drunk would say to the writer, 'Come on, you idiot. Let's get some good out of that portable. Let's hock it. Let's take it to that pawn shop over on Third Avenue. It's always good for ten dollars. Another drink, another binge, another bender, another spree.' Such humorous words. I've tried to break away from that guy a lot of times, but no good. You know, once I even got myself a gun and some bullets. I was gonna do it on my thirtieth birthday. Here are the bullets. The gun went for three quarts of whiskey. That other Don wanted us to have a drink first. He always wants us to have a drink first. The flop suicide of a flop writer.
Wick: All right, maybe you're not a writer. Why don't you do something else?
Don: Sure, take a nice job, public accountant, real estate salesman. I haven't the guts, Helen. Most men lead lives of quiet desperation. I can't take 'quiet desperation.'
Helen: But you are a writer. You have every quality for it - imagination, wit, pity.
Don: Come on, let's face reality. I'm thirty-three. I'm living on the charity of my brother. Room and board free. Fifty cents a week for cigarettes and an occasional ticket to a show or a concert - all out of the bigness of his heart. And it is a big heart and a patient one...I've never done anything, I'm not doing anything, I never will do anything. Zero, zero, zero!

Believing that he is a terminal drunk and a "zero" person who lives off his brother's charity, Don challenges Helen to leave him ("Look Helen, do yourself a favor. Go on, clear out"), but she lovingly refuses to admit that either of them are defeated: "I'm gonna fight, and fight and fight..."

End of Flashback # 2

The film returns to the present with a pan left and dissolve back to Nat's bar: "That was three years ago, Nat. That's a long time to keep fighting, to keep believing. She knows she's clutching a razor blade but she won't let go. Three years of it." Resolute, Don vows to become the accomplished writer Helen has always believed him to be:

I'm gonna do it now. It's all there, you heard it...That's why I didn't go away on that weekend, see, so I can be all alone up there and sit down at my typewriter. This time, I'm gonna do it, Nat! I'm gonna do it!...I'm going home. This time, I've got it. I'm gonna write.

He returns home and determinedly types out three lines on the title page to his novel:

And then looking quite haggard, he lights a cigarette, rubs his neck, struggles, sweats, and puffs in front of his almost-blank page. Alcohol cravings seize his mind as he again slides into his self-induced hell and tears apart the apartment in search of a hidden bottle. After overturning his mattress, books on his shelves, a lamp, and items in his closet, he collapses in his arm chair next to his empty 93 proof whiskey bottle and glass. He notices the inside of a matchbook cover, advertising "Harry and Joe's - Where Good Liquor Flows" at 13 West 52nd Street in NYC.

He sinks deeper into his delirious world of alcoholism, falls off the wagon and ends up at the cocktail lounge - unable to pay the expensive bill when his money runs short after many high-priced drinks. Noticing the monogrammed handbag (MM) of the young lady next to him, Birnam ruthlessly steals the purse, takes it into the washroom, and removes $10 from it. When he returns to his table, he is confronted with the theft. The 'cheap drunk' quickly returns the purse and money, but cannot pay the check. The pianist leads the customers in singing Somebody Stole A Purse to the tune of Somebody Stole My Gal as he is thrown out into the street, protesting: "I am not a thief!"

He stumbles back to his disheveled apartment (with an overturned lampshade looming up in the foreground) that evening, feeling miserable, debased, and defeated, until he lies down and sees the glowing shadow of a bottle that he hid in the lighted fixture above him.

Saturday:

After surrendering to another night of suicidal binging, he awakens to the incessant, annoying sound of the ringing telephone. The scene opens with an intense closeup of Don's haunted-looking, hung-over right eye. His hollow, gaunt face is covered with bearded stubble, and his clothes are messed up - he slept without removing them. He shouts at the unanswered phone: "Stop it, Helen, stop it, stop it. I'm all right. I just can't talk. Please stop it!" With both whiskey bottles empty, he decides to pawn his own typewriter for booze money to satisfy his cravings for demon drink. But he worries about the distance he must walk: "You'll never make that hock shop. It's a block and a half away." He leaves his apartment, stepping over the two bottles of milk and newspapers lying in front of his door, and exhaustedly trudges along down Third Avenue. Throughout most of the day, he drags himself about forty or fifty endless blocks on Third Avenue toward 90th Street. His desperate attempt to pawn his only means of livelihood are fruitless - eventually, he discovers that the shops are closed behind iron gratings due to the Jewish holiday of Yom Kippur. Both Jewish and Catholic pawnshops are simultaneously shut.

He stumbles back to Nat's Bar where he collapses and begs: "Let me have one, Nat. I'm dying. Just one." The broken-down Birnam endures the bartender's refusal to serve him ("No credit and you know it"), eventually wearing him down and getting one shot's worth. Nat whets his appetite and then orders him out of the bar for his own good: "Yeah, one. One's too many, and a hundred's not enough. That's all...Now go, go away...I mean it, get out of here!"

On his way back home, Birnam passes the wooden Indian statue below where Gloria said she lived. When he buzzes her second-floor apartment door, she sarcastically reproaches him for being a "little late" for their Friday night date and rejects any apology: "Save your saliva. I've had enough of you...What do you think I am? I break a business date. I buy me an evening purse, a facial, and new hairdo, and maybe you can do that to your ritzy friends, but you can't to me, understand?" Pitifully, he beseeches her for "some money" and kisses her. She softens toward him, admitting: "I waited half the night like it was the first date I ever had. The other half I was crying." She gives him a $5 bill and asks insecurely: "You do like me a little, don't ya, honey?" As he leaves exhausted and trembling, in a subjectively-shot scene, he slips and falls down the flight of stairs from her apartment.