Back at his apartment, Ann finally awakens at about 1:30 in the afternoon, but she is thoroughly disoriented:

Ann: Would you be so kind as to tell me where I am?
Joe: Well, this is what is laughingly known as my apartment.
Ann: Did you bring me here by force?
Joe: No, no. Quite the contrary.
Ann: Have I been here all night, alone?
Joe: If you don't count me, yes.
Ann: So I've spent the night here - with you?
Joe: Well now, I-I don't know that I'd use those words exactly, but uh, from a certain angle, yes.
Ann: (beaming with a smile) How do you do? (She extends her hand for a handshake)
Joe: How do you do?
Ann: And you are - ?
Joe: Bradley, Joe Bradley.
Ann: Delighted.
Joe: You don't know how delighted I am to meet you.
Ann: You may sit down.
Joe: (sitting on the bed) Thank you very much. What's your name?
Ann: You may call me Anya.

The newspaper reporter pretends ignorance of her identity, initially having a strictly mercenary interest in the Princess. (Deception #5) While she takes a bath, he phones his carefree, bearded photographer friend Irving Radovich (Eddie Albert), hinting: "It's front-page stuff. That's all I can tell ya. It might be political or it might be a sensational scam. I'm not sure which. But it's a big story, and it's gotta have pictures."

Everything is exciting for Ann: "It must be fun to live in a place like this." But she feels compelled to leave and wander around by herself. After lending her a little money, he secretly follows her through the crowded streets and marketplace filled with small motorcycles, bicycles, vendors, and pedestrians. She walks the streets of Rome incognito, experiencing things as an ordinary commoner and doing things exactly the way she wants to. At a salon, she has her hair drastically cut shorter after ordering the Italian haircutter (Paolo Carlini): "All off." Afterwards, the salon hairdresser asks: "You musician, maybe? You artist? Painter? I know, you model," and she seems to agree with his inaccurate assessment. She tells him that the drastic hairstyle makes her unrecognizable: "It's just what I wanted."The flirtatious barbiere invites her to go dancing for "moonlight, music, romantic." She again affirms that her friends will not recognize her new look: "I don't think they will." (Deception #6)

She begins her day of freedom by ordering a gelati cone at a roadside stand and accepting a single flower from a flower vendor. Joe accidentally runs into her to keep in contact with her and get the inside information for his story. (Deception #7) She confesses her predicament of playing hookey from school and her desire to "live dangerously":

Ann: I ran away last night, from school.
Joe: Oh, what was the matter? Trouble with the teacher?
Ann: No, nothing like that.
Joe: Well, you don't just run away from school for nothing.
Ann: It was only meant to be for an hour or two. They gave me something last night to make me sleep.
Joe: Oh, I see.
Ann: Now, I'd better get a taxi and go back.
Joe: Well look, before you do, why don't you take a little time for yourself?
Ann: Maybe another hour.
Joe: Live dangerously. Take the whole day.
Ann: I could do some of the things I've always wanted to.
Joe: Like what?
Ann: Oh, you can't imagine. I-I'd do just whatever I liked all day long.
Joe: You mean things like having your hair cut, eating gelati...
Ann: Yes, and I'd sit at a sidewalk cafe and look in shop windows. Walk in the rain, have fun and maybe some excitement. Doesn't seem much to you, does it?

Joe proposes to spend the day with her and experience everything she has always wanted to:

Joe: Tell you what. Why don't we do all those things, together?
Ann: But don't you have to work?
Joe: Work? No. Today's gonna be a holiday.
Ann: But you want to do a lot of silly things?
Joe: (He takes her hand) ...First wish? One sidewalk cafe, comin' right up. I know just the place. Rocca's.

At the cafe, Ann orders costly champagne for lunch, and then describes, in disguised terms, her father's fortieth anniversary of the day he got his job:

Ann: Well, mostly you might call it public relations.
Joe: Oh, well, that's hard work.
Ann: Yes. I wouldn't care for it.
Joe: Does he?
Ann: I heard him complain about it.
Joe: Why doesn't he quit?
Ann: Oh, people in that line of work almost never do quit, unless it's actually unhealthy for them to continue.

To conceal his own identity to her, (Deception #8) Joe describes his own line of work, falsifying that he is a successful businessman who sells "fertilizer, chemicals"):

Ann: What is your work?
Joe: Oh, I'm, ah, in the selling game.
Ann: Really? How interesting. What do you sell?
Joe: Fertilizer. Chemicals. You know, chemicals. Stuff like that.

When Irving arrives, he repeatedly tries to mention that Ann is a "ringer" for the Princess, but Joe blocks him by kicking him under the table, dumping a drink in his lap, and finally by knocking his chair over. When Joe gets Irving away for a few moments, he tells his photographer friend about Anya Smith's ("Smitty's") real identity and the promise of five grand (including a percentage of the take if there are pictures) if they can keep it a secret (Deception #9): "She doesn't know who I am or what I do. Look Irving, this is my story. I dug it up. I've got to protect it...Your tintypes are gonna make this little epic twice as valuable...You're in for twenty-five percent of the take." Then, he asks his friend to loan him thirty thousand lira ("that's fifty bucks") so that he can entertain the Princess for the rest of the day.

Ann smokes her "very first" cigarette, while Irving surreptitiously takes candid pictures of her with his hidden-camera cigarette lighter. Meanwhile, "plain-clothes" men are retained to search the city for the missing princess, as Joe, Ann, and Irving begin their carefree tour of the city on a "fun schedule." She rides on the back of Joe's motorcycle to see the famous sights, including the ruins of the Coliseum.

After Ann recklessly drives them through the streets, they are arrested by the polizia but released after Joe's clever alibi: "Going to church to get married on a scooter." (Deception #10) Ann brags about her own deceitfulness:

Ann: I'm a good liar too, aren't I, Mr. Bradley?
Joe: The best I ever met.

In a memorable scene, Joe shows the Princess a sculpture which he names 'The Mouth of Truth.' He tests the legend with her:

Joe: The Mouth of Truth. Legend is that if you're given to lying, you put your hand in there, it'll be bitten off.
Ann: Oh, what a hard idea.
Joe: Let's see you do it.
Ann: (she nervously moves her hand toward the mouth, but then pulls back) Let's see you do it!

Joe scares the Princess into believing he has lost his hand inside the sculpture's mouth, (Deception #11) and she is amused by the surprise of his joke and laughs.

Later during her guided tour, they visit a wall covered with inscriptions, where wishes are supposed to come true. Joe suggests that she make a wish, but she keeps her desire private and adds: "Anyway, the chances of it being granted are very slight":

Joe: Each one represents a wish fulfilled. It all started during the war. There was an air raid, right out here. A man with his four children was caught in the street. They ran over against the wall, right there, for shelter and prayed for safety. Bombs fell very close, but no one was hurt. Later on, the man came back and put up the first of these tablets. Since then, it's become a sort of a shirine. People come and whenever their wishes are granted, they put up another one of these little plaques.
Ann: Lovely story.
Joe: Read some of the inscriptions. (Ann moves closer toward the wall) Make a wish? (Ann nods). Tell the doctor?
Ann: (declining) Anyway, the chances of it being granted are very slight.

Ann suggests going dancing that evening on a barge down by Sant'Angelo on the Tiber River (where she was invited to meet the salon barber) - to stay out later, but Joe senses a premonition that it will end her fairy-tale life:

Ann: At midnight, I'll turn into a pumpkin and drive away in my glass slipper.
Joe: And that will be the end of the fairy tale.