HENRI: She's an enchanting girl, Adam. Not really beautiful. And yet, she has great beauty.
We think this is a compliment? Maybe? Henri's description of Lise to Adam reveals a lot about gender expectations and how we view beauty. Henri's saying that, on the outside, Lise isn't a stunner, but she makes up for her lack of "traditional" beauty through her complexity.
YOUNG WOMAN: I can understand disregarding perspective to achieve an effect, but in your case—
JERRY: Look, honey. Why don't you be a good little girl and move on. You're not going to buy anything. You're just blocking out the sunshine.
YOUNG WOMAN: Well, I just wanted to discuss your work.
JERRY: I don't want you to discuss my work. I'm not interested in your opinion of my work. If you say something nice, it won't make me feel any better. If you don't, it'll bother me. Thank you. Good day.
If the young woman were a young man, do you think Jerry would've told him to be a "good little boy" and move on? Probably not. This exchange suggests that Jerry doesn't value this young woman's opinion simply because she's a young woman.
JERRY: Hey, uh, how'd you come by all these worldly possessions? A rich husband or a rich father?
For Jerry, the idea that Milo could've made her fortune by herself is about as realistic as electing a Labradoodle president of the United States. Furthermore, the fact that Milo takes no offense also reflects the time period's prevailing attitude about gender.
JERRY: That's, uh, quite a dress you almost have on.
JERRY: What holds it up?
Milo's not above using her feminine wiles to try to snag Jerry. Personally, we'd prefer to see her use her brain, but that was then and this is now. Jerry, meanwhile, is just surprised to see a powerful woman actually look like a woman. For Jerry, and most of society at the time, power and femininity were mutually exclusive.
MILO: I don't need a paid escort, and I'm not trying to rob you of your precious male initiative. I'm simply interested in your work and I want to get to know you better. Now is that such a crime?
Taking a hand-out from somebody is hard enough for Jerry—but taking a hand-out from a woman? That really threatens his pride as a dude.
MILO: Would it embarrass you if I signed the check?
JERRY: Yeah. Let's go someplace I can afford.
Of course he'd be embarrassed; it's the 1950s. Jerry may be okay with Milo sponsoring his career behind the scenes, but he's not going to let her pick up the check in public. We mean, what would the waiter say?? Probably nothing, but that doesn't matter to Jerry. Men are supposed to pick up the check.
LISE: I don't know what type of girl you think I am, but I am not, and now I would like return to my friends.
JERRY: I thought you were bored with them. You sure looked it.
LISE: You should see me now.
Atta girl, Lise. When Jerry first meets Lise he comes on strong—like "Lise should seriously consider a restraining order" strong—so when she isn't won over and takes Jerry down a peg in the process, he's surprised. Ouch, indeed.
ADAM: (to Jerry) Tell me: when you get married, will you keep your maiden name?
Here, Adam equates needing financial support with being a woman, giving a tidy summary of gender attitudes in the film.
ADAM: I told you this sponsoring business was complicated. You see what happens today? Women act like men and want to be treated like women.
Before you hate on Adam, we should probably tell you that his views are a pretty accurate reflection of his society's attitudes about gender. Of course, that doesn't make them any less awful, but that's the way things were.
JERRY: You and I are going out tonight. I'm going to take you to the art students' ball. You ever been to one?
JERRY: You'll love it. It's jet-propelled New Year's Eve, and everybody in Paris will be there.
MILO: It's costume, isn't it?
JERRY: Nevermind. I'll take care of all that. Leave it to me. Tonight's my night.
MILO: I feel like a woman for a change.
We'd be a lot happier for Milo if this weren't such a bummer of a conversation. Here's why: Milo's reaction suggests that she can't be rich, powerful, and in charge, and also be a woman. She can be one or the other, but not both.