In "the Mansion," the millionaire escorts his new-found friend back to his elegant mansion to warm up. The millionaire's butler (Allan Garcia) tells him that his wife has sent for her baggage following their divorce or separation. The millionaire hurls his wife's photograph from the top of the liquor cabinet. The two buddies have a few strong champagne toasts to their friendship, although half of the bottle ends up down the Tramp's pants. The Tramp finds that the butler doesn't like him. The millionaire becomes depressed about his marital situation, reminded by the butler's news, and attempts suicide again with a revolver, but the Tramp prevents a second suicidal attempt on his life. The millionaire brightens up and suggests that they go out to a night club together: "We'll burn up the town!" They dress to go out on the town to celebrate.

In "Out on the Town," they enter a crowded dinner and dance nightclub together. The Tramp's behavior causes a series of unfortunate incidents to occur there. He slips on the polished floor, and also sets fire to a lady's dress with his discarded cigar butt. She is squirted with seltzer water to put the fire out. In a hilarious spaghetti-confetti sequence, he confuses the spaghetti on his plate with the strings of streamers which come floating down from the ceiling. He finds himself helplessly sucking upward on an endless strand of noodle. After a brief floor show - an Apache dance - the drunken Tramp attempts to save the female dancer from her partner. The rhythmic beat of the dancing possesses the Tramp. First, he passionately and wildly whirls an unsuspecting woman around on the dance floor. And then he takes a waiter with a food tray as his partner. Exhausted by the energy he has expended, he falls stiffly backward, collapsing into the arms of the millionaire.

In "Homeward Bound," the two of them zig-zag home in the millionaire's Rolls-Royce, in the early morning. The Tramp reprimands his companion for his reckless driving: "Be careful how you're driving" but receives a reproach: "Am I driving?" They cross over sidewalks, and narrowly avoid other cars.

In "Come In, Get Out, Come In," they arrive back at the mansion, and the Tramp is offered the limo: "Keep it, it's yours." The butler throws the Tramp out onto the front steps, where he sees the Flower Girl pass by. At his millionaire friend's orders, he is fetched back inside. The Tramp is lent some money to go buy some flowers, although the butler disapproves. He runs after the Flower Girl in the neighborhood and with the real millionaire's money buys up her whole basket of stock for ten dollars. He gives her one bill: "Here's ten dollars." When she replies: "I haven't any change, sir," he refuses the change and then thrusts a second bill into her hands. The Tramp drives her home in the rich man's car - he literally becomes the person she imagines with the money and automobile in his possession.

As they pull up in front of her place, a cat is seen sitting on a high windowsill. She thanks him for his kindness and he asks: "May I see you home again?" The blind girl responds: "Whenever you wish, sir." Once again, she is infatuated by his attention to her, now mistakenly convinced that he is a real millionaire. He is content to let her believe that he is very rich. As he smells the boutonniere, the cat from above knocks a flowerpot on his head, but he is so love-struck that he shrugs off any hurt. He climbs up and stands on a large rain barrel to yearn after her from her second floor window. The fat janitor from below catches him peeping and startles him. The barrel topples over and water floods down on the man as the Tramp scampers away to the limo.

In "This Time, Stay Out," he returns to the millionaire's mansion in the limo, but the eccentric millionaire has sobered up, and can remember nothing at all of what has happened. He has to be drunk to recognize the Little Tramp as his friend. When sober, he is icy and cold and wants nothing to do with the Tramp. When drunk, he is friendly and supportive. The Tramp is pushed out by the butler at the front door and goes away disappointed. He trails a gentleman down the street for his discarded cigar butt - in the borrowed limousine. He leaps from the car to elbow another bum away from the discarded cigar butt.

In "Daydreams," the Blind Flower Girl thinks of her millionaire friend, and tells her grandmother: "...and then he brought me home in his car." Her grandmother thinks: "He must be wealthy." She replies: "Yes, but he's more than that."

In "That Afternoon," the Tramp again meets the drunken millionaire on one of the city's sidewalks. He welcomes his "friend" again with open arms, and arranges a "swell party" in his honor. At the party, the tipsy Tramp mistakes a bald head for fancy ice cream or a cream pudding. When he is offered real pudding, he dismisses it. And then he swallows a whistle, a party favor. With an attack of hiccups, he whistles with each spasm. When he steps outside to avoid distracting the other guests, he first attracts a taxi, and then is surrounded by a wild assortment of dogs.

In "The Morning After," morning brings an unpleasant awakening. He finds himself sharing a warm double bed with the millionaire, who wakes up sober and doesn't recognize him at all. Once again, the Tramp is ruthlessly ordered out of the mansion. The millionaire is planning an ocean voyage to Europe, leaving at noon. After being thrown out by the butler and neatly stealing some fruit on the way, the Tramp pulls a banana from his back pocket and strolls away unperturbed, non-chalantly peeling the banana and taking a bite. Disillusioned again, the Tramp tries to find the Blind Girl at her familiar street corner location, but she is not there. Looking through her home's window, he learns that she is sick in bed with a fever, attended by a doctor and her grandmother. He sits dejectedly on the stairs where he was earlier hit with a falling flowerpot.

In "Determined to Help," the Tramp finds his purpose in life. He is determined to pay for a doctor and become her benefactor, so he takes a job as a street cleaner, a sanitary engineer with a shovel and a trash barrel. Shuffling along in his white street-sweeping uniform, he sees the natural remains of a horse-drawn cart - and shovels up the manure. He turns away from following a long procession of mules, and then he does a double-take when an elephant ambles down the street, part of a circus animal procession. The girl's grandmother shields her from the bad news - they have received a Final Notice of $22 rent due, facing eviction from the dispossessing landlord who has signed the notice: M. B. Mint. The blind girl is hopeful: "He's coming today!" At lunch time during his work break, the Tramp accidently swaps soap for a wedge of cheese, providing a fellow laborer with a soap sandwich. Bubbles float from the worker's mouth as he is cursed. The Tramp is warned about being back on time for his job.

In "Playing the Gentleman," "to play the part of a gentleman without the millionaire was difficult, but he did his best." He takes food to the girl at her home, delighted at being able to play the role as breadwinner. The blind girl's grandmother is not at home when he calls. The Tramp empties the largesse from a bag - fruit, a head of cauliflower (that looks like a giant boutonniere), and a plucked duck. The Tramp reads to her from the newspaper about a Viennese eye specialist in town who can cure her blindness. "Wonderful, then I'll be able to see you," she says, giving him some hesitation and cause for alarm. The gift of sight that he wishes to give her may also cause tremendous loss. She asks him to hold the skein of yarn she is raveling up. But his joy turns to concern when he realizes that she has somehow caught a loose thread from beneath his vest that is slowly unraveling his long underwear. As he continues to talk to her, he squirms and writhes as the threads from his underclothes slither against his skin and he is slowly stripped of his undergarments. He shifts from side to side so that the unraveling won't catch somewhere. Then, he feverishly pulls the thread out to feed it into her hands until there is nothing left.

The Tramp also reads to her the Final Notice about overdue rent, upsetting the girl. But he promises: "Now don't worry. I'll pay it the first thing in the morning." He returns to his street-sweeping job, but loses it for being late once too often. His employer fires him: "You're late for the last time!" As he walks away, he is enticed into making some "easy money" outside the Main Street boxing arena.

In "That Night," to keep up pretenses of being rich and to earn reward money to pay the overdue rent, he enters a fixed boxing contest. As a stand-in, he must not hurt his crook-opponent, and the plan is to split the purse 50-50 following the match. He believes that the fight is fixed in his favor.