In the next car, Sugar asks Joe to put the ice in the sink and Joe warns her that they should stop because if Bienstock catches her she will be thrown out of the band. “I’m not very bright I guess!” Sugar says. When Joe protests, Sugar insists that if she were brighter she wouldn’t have to play with such a “crummy band,” that she used to work with male bands, but that she cannot “afford” to anymore. She then seductively tells Joe that she has a thing for saxophone players, which catches his attention. “You know, I play tenor sax,” he says to Sugar, to which she responds, “Yeah, but you’re a girl, thank goodness!” Sugar then tells Joe that she feels safer in an all-female band, because men are so untrustworthy, that they spend all their money on other girls and gambling, and then just leave one day. “I’ll tell ya one thing, it’s never gonna happen to me again. I’m tired of getting the fuzzy end of the lollipop!”
They are suddenly interrupted by one of the girls, who asks what’s taking so long with the ice. Joe asks the girl to bring them back some drinks, and Sugar tells him that she’s turning 25 in June, which has gotten her to thinking about getting married, which is why she’s excited about going to Florida. When Joe asks her what is so special about Florida, she informs him that Florida is filled with “millionaires…flocks of them! They go south for the winter like birds!” Sugar then tells Joe that she wants to meet a man with glasses, because they are more gentle. A girl brings them drinks and Joe raises a toast to “the sweet end of the lollipop.” Back in Jerry’s bunk, a crowd of girls are drinking, smoking, and giggling loudly.
Suddenly Jerry starts hiccuping. One of the girls puts some ice on Jerry’s neck and it falls down the back of his nightgown. As the girls try to get the ice out from Jerry’s nightgown, it becomes apparent that he is quite ticklish and the girls tickle him, which makes him so nervous that he pulls the emergency brake for the train. The train stops, and we see Joe falling onto Sugar in the next car. When he goes to see what happened, the girls are all scrambling back to their bunks to avoid being found out. Just as Jerry climbs back into his bunk, Sweet Sue pops out angrily from her bed and asks what’s going on, calling on Bienstock for help. Bienstock scrambles out of bed as well, but they find nothing wrong.
The scene shifts and we see a palm-tree-lined street in Florida. We see a bus pulling up to a large beachside hotel and a group of bespectacled millionaires sitting on the hotel porch, rocking in rocking chairs and reading the paper. The girls stream off the bus as the millionaires watch, smiling. As Sugar gets off the bus with Joe and Jerry, Jerry offers to carry their instruments. Joe and Sugar then go into the hotel, leaving Jerry with armfuls of instruments alone. “Isn’t she a sweetheart?” Joe says to Sugar. On the porch, Sugar and Joe see the millionaires, whom Sugar notes all seem to be over 75 years old. “Let’s hope they brought their grandsons along,” Sugar says, as they go into the hotel. As Jerry approaches the hotel, one of the millionaires sitting at the end smiles and helps him put his shoe (which has fallen off) back on. He introduces himself to Jerry as Osgood Fielding III. Jerry seems uncomfortable as Osgood tells him, “If there’s one thing I admire, it’s a girl with a shapely ankle!” Osgood then offers to carry one of the instruments and Jerry gives him all of them.
Inside, Osgood continues to talk to Jerry, telling him that it’s nice to have some young people around and that he loves show business and “invests” in showgirls. While they wait for the elevator, Osgood tells Jerry that he’s been married 7 or 8 times and that his “mamma” sent him down to Florida to go “deep sea fishing,” but doesn’t know that he is on land looking for a new wife. “Pull in your reel,” an uncomfortable Jerry says to Osgood, gently pushing him away. When Osgood asks him out to dinner, Jerry insists that he will be playing in the band later, and they have a suggestive conversation about instruments. The elevator doors open and Jerry thinks he has an opportunity to get away, but Osgood follows him on. As the elevator doors close, the camera pans up to the floor numbers. The arrow goes up to the 2nd floor, but then the elevator seems to come immediately back down. As the doors open again, Jerry scolds Osgood—“What kind of girl do you think I am, Mr. Fielding?”—before slapping him. Evidently, Osgood got fresh with Jerry on the elevator.
Jerry storms out of the elevator and climbs up the stairs, as Osgood tries to convince him to stay. Upstairs, Bienstock announces the girls’ room assignments, but he cannot find his glasses, so Sweet Sue reads it. “Daphne” and “Josephine” are staying together in the room next to Sugar and a girl named Dolores. As they walk to their rooms, Sugar tells Joe that she wishes they were in the same room, but Joe assures her that they will see a lot of each other. At her room, 414, Sugar notes that her room in Cincinnati was 414 when she was playing with a male band and dating the saxophonist. Joe tries to comfort Sugar, telling her that his “feminine intuition” makes him sure that Sugar is going to meet a millionaire. After Sugar goes into her room, Joe goes into his, where he runs into a young bellboy who aggressively flirts with him. Joe tells him to get lost, which only encourages the boy more, who says, “That’s the way I like ‘em! Sassy!” before leaving.
Joe throws down his purse and stores his suitcase under the bed, as Jerry enters. Jerry is angry and tells Joe that he “just got pinched in the elevator.” Joe assures Jerry that men do not care if a woman is pretty; they just see a woman in a dress and are smitten. Jerry tells Joe that he wants to leave, reminding Joe that it was his idea to leave the band as soon as they got to Florida. Joe, however, reminds Jerry that they are broke and on the run from Spats Columbo, so need to stay incognito. He then reminds Jerry that they are getting paid, that they get room and board, and they are in a beautiful place. Jerry doesn’t buy Joe’s speech, however, and accuses him of wanting to stay for Sugar. “We’re like sisters!” Joe insists, but Jerry promises to keep an eye on them for the duration of the tour. Suddenly there’s a knock on the door. It’s Bienstock, who enters the room once Jerry gets his wig on and asks if they have seen his suitcase. Apparently, Bienstock’s glasses and suitcase have gone missing. Sugar comes into the room beside him to fetch her ukulele and tell Joe and Jerry that the girls are going swimming.
When Jerry agrees to go swimming, Joe reminds him that he doesn’t have a bathing suit, but Sugar tells them that they can rent them. Joe tells Sugar that she’s going to stay in and take a bath, but Jerry agrees to go along. Once Sugar and Jerry have left, Joe locks the door and pulls a suitcase out from under the bed. It is Bienstock’s missing suitcase, and Joe pulls out a nautical cap and then pulls Bienstock’s glasses out of his garter and puts them on. The scene shifts to the beach, where the girls run into the water excitedly. Jerry splashes Sugar and plays with her, as Joe walks down the beach towards the group, dressed now as a man, in Bienstock’s clothes. As the girls run back onto the beach from the water, Joe watches them from a distance. For the first time, Sugar notices that Jerry has big arms and a flat chest, and one of the girls initiates a game of beach ball.
As the girls start their game, Joe intimidates a little boy so that he can steal his beach chair and watch. The girls chant and toss the ball around the circle. When one of the girls hurls the ball too far and it goes flying towards Joe in his beach chair, Sugar runs after it. When she gets near Joe’s chair, he trips her as an excuse to start a conversation. Affecting a bad British accent, Joe plays the role of an eccentric young millionaire, in hopes of winning Sugar’s affections. Picking up a paper, Joe sits back down in the chair and refuses to tell Sugar who he is, having suitably intrigued her. Jerry calls Sugar back to the game aggressively, noticing that Sugar’s attention has gone elsewhere. Sugar throws the ball back and tries to make conversation with Joe, who answers in one word answers between reading his paper. After hinting that she has probably seen him in a magazine, Joe tells Sugar that she’s blocking his view of his yacht. Overjoyed to hear that he has a yacht, Sugar asks him if his is the big one, and Joe tells her that “with all the unrest in the world” he doesn’t feel comfortable having a yacht that sleeps more than 12. He then lets her know that he is unmarried and Sugar kneels beside his chair.
Sugar tells him she’s there with a band and he asks if she plays jazz. She tells him that they do—“real hot!”—to which Joe responds, “I guess some like it hot. I personally prefer classical music.” Trying desperately to keep up the conversation, Sugar pretends that she prefers classical music as well, telling him that she went to a conservatory and that she is really rebelling against her high society family by being in the jazz band. Joe and Sugar, both posing as upper-class individuals, bemoan the drudgery of their wealthy upbringings. Sugar tells Joe that she has a theory about men who wear glasses, but that she’ll wait to tell it to him when she knows him better, before asking him what he’s doing that evening and inviting him to see the band play. Unfortunately, Joe says, he only comes to shore twice a day, when the tide goes out, to collect shells, as that is what his father and his grandfather did. “You might say we have a passion for shells—that’s why we named the oil company after it,” he tells her.
Sugar’s eyes widen as she realizes that Joe is insinuating that his family owns Shell, a giant oil company, which suggests that he must be exceedingly wealthy. Just as Joe is telling Sugar to call him “Junior,” Jerry runs up and tells Sugar that it’s time for dinner, causing Joe to cover his face, fearful of being found out by his friend. When Sugar tells him that she will catch up with the girls later, Jerry starts to run off towards the hotel. Jerry stops short, however, when he realizes that it’s Joe in the chair. Joe passes off Jerry’s accusatory finger point as his recognizing him from the papers. Sugar is overjoyed, telling Jerry that she recognizes him too, and explaining that Joe is waiting for his yacht. Jerry is perplexed, and Sugar introduces him as “Daphne…a Vassar girl,” trying to impress Joe. “I’m a what?!” Jerry says, as Sugar motions for her to play along. Joe stands and says, “I heard a very sad story about a girl that went to Bryn Mawr. She squealed on her roommate... and they found her strangled with her own brassiere!” and looks at Jerry menacingly. Without skipping a beat, Jerry says, “Yes, we've got to be very careful who we choose for a roommate.” Jerry and Sugar say their goodbyes, and Joe watches them go. Looking back, Sugar is excited about her new millionaire friend, and tells Jerry that she “can’t wait to tell Josephine.” Seeing an opportunity to reveal Joe as a fraud, Jerry says that they ought to go up to the room and tell her right then and there, grabbing Sugar’s arm and pulling her towards the hotel.
Inside, Jerry and Sugar run into their hotel room and call for Josephine. When Joe is not there, Jerry encourages Sugar to stay and wait for “Josephine,” hoping that this will reveal that Josephine is in fact, Junior, who is, in fact, Joe. When Sugar wonders if Josephine went shopping, Jerry laughs and says, “Shopping, that’s it! Something tells me she’s going to come through that door in a brand new outfit!” Suddenly, they hear someone singing in the bathroom. It’s Joe, singing in his girlish Josephine voice, taking a bath. “Oh, I didn’t hear you come in!” Joe says from a bubble bath as Jerry and Sugar open the door. Jerry is shocked and confused about how Joe beat them up to the room. Sugar sits beside the bath and tells Joe that she met a millionaire on the beach, describing “Junior” as “a real gentleman, not one of these grabbers,” and “Josephine” urges Sugar to go after him. Sugar assures Josephine that Junior will be at their concert tonight, a conviction that Jerry echoes vehemently, hoping to complicate Joe’s plot and foil him.
While Joe has been the one to keep it together for much of the movie, barely getting thrown off by the presence of so many beautiful women, his one-on-one conversation with Sugar begins to unravel his composure. Yet again, Sugar knows exactly the things to say to entice the disguised men. When Sugar brings up the topic of men, Joe thinks that she is about to confide her distaste for men, but she instead tells “Josephine,” “I don’t trust myself, I have this thing about saxophone players.” Joe, a saxophone player, is instantly startled to realize that if he were not dressed as Josephine, he would have a very good shot of having an affair with Sugar, which creates a crack in his hitherto sturdy veneer of femininity. Walking towards Sugar in a trance, he drops his feminine voice and looks about ready to kiss her. The film gets a great deal of use out of this joke, that Sugar is at once completely sexually available to Joe and Jerry, yet because of their female disguises, totally unavailable.
Sugar’s unavailability is not just the result of the fact that Joe and Jerry are dressed up as women, but also—as she details soon after revealing her weakness for sax players—connected to her distrust of men. Even though Sugar has a weakness for the opposite sex, she also sees right through them, and tells “Josephine” that men just tell a woman that they love them, before spending their money on other women and gambling it away. Joe, a gambler himself, is forced to look at himself as an untrustworthy suitor in this moment, in spite of his pronounced attraction to Sugar. Thus, not only is the attraction between Joe and Sugar impossible because of Joe’s disguise, but also because Sugar wouldn’t trust him if she knew he was a man anyway. The only reason she feels comfortable confiding her true feelings about men in Joe is that she believes he is “Josephine,” a kindly, matronly female saxophone player.
The film is always very lighthearted, maximizing comedic effect and style in favor of strict realism. For instance, the scene of the party on the train is exaggerated and over the top. The girls smoke and swig booze in their bunks, laughing raucously even though they are on a cramped train in the middle of the night and could easily be found out. The din of female laughter and chatter is a recurring comedic element of the film, with the girls in the band often having outlandishly enthusiastic and loud reactions to various moments. This serves to heighten the band members’ girlishness as it contrasts with Joe and Jerry’s performances of femininity. Additionally, Joe and Jerry’s female impersonations are not especially believable; to the viewer, their maleness seems rather apparent, but it goes almost completely unnoticed by the girls in the band. Even when Joe and Jerry accidentally drop their voices down an octave, Sugar and the other girls seem blissfully unaware that their ranks have been invaded by two men. This heightens the dramatic irony, the fact that we as the viewer know that they are men, but the other characters have no idea.
The use of comedic storytelling only heightens once the group makes it to Florida. The first image of their hotel that we see is a group of bespectacled millionaires in identical white hats—Sugar Kane’s version of the ideal husband—rocking in rocking chairs, folding up their papers, and removing their glasses in perfect unison. It is a completely outrageous sight, heightened and choreographic, meant to communicate not only the sheer number of millionaires who “flock” to Florida in the winter, but also their indistinguishability from one another. Much as all the girls in the girls’ band seem to be part of the same unit, a bevy of excitable blondes who love to party, the millionaires at the hotel are also connected to one another. The movie makes use of very specific “types” in order to make a joke and to highlight patterns and dynamics that the audience can recognize. The stereotype of the gold-digging blonde ditz and her adoring millionaire husband is exploited by the film in surprising and hilarious ways.
While the tone of the film is quite lighthearted and over-the-top, it makes a number of complicated and interesting observations about gender and sexuality. When Joe and Jerry arrive at the hotel, they are greeted by lasciviousness everywhere they turn. Osgood Fielding takes an instant and predatory liking to “Daphne,” pinching her butt in the elevator and “Josephine” cannot even get unpacked without getting hit on by a prepubescent bellboy, who is undeterred by Josephine’s insistence that he leave. “Just the way I like ‘em: sassy!” the boy says to Josephine’s. Forced to walk in women’s shoes (literally), Joe and Jerry begin to see just how lecherous men can be and how cautious and prudent the average woman must be. Even though they themselves are men, easily swayed by pretty girls themselves, Joe and Jerry’s appearance as women in an all-girl band forces them to confront some of the difficulties of male entitlement. Jerry complains about Osgood’s unwanted attention saying, “I’m not even pretty!” but Joe assures him, “They don't care. Just so long as you're wearing a skirt. It's like waving a red flag in front of a bull.” While the film seems to accept or at least remain ambivalent about these dynamics, it also shows makes clear the difficulties of being a woman in a world of men.