Higgins: I’m interested. What about the ambassador’s garden party? I’ll say you’re the greatest teacher alive if you make that good. I’ll bet you all the expenses of the experiment you can’t do it. And I’ll pay for the lessons.
Pickering shares with Higgins a penchant for language, and so when he speaks these lines to Higgins in Act 2, he is genuinely interested in seeing Higgins’ skill as a teacher in action. That he offers to pay for the lessons also speaks to his ostensibly generous nature, a stark contrast to Higgins’ lack of generosity and consideration throughout the play, though it’s a generosity that’s complicated by personal interest and short-sightedness; he, like Higgins, hasn’t at this point given any thought to what will become of Eliza once the experiment has concluded.
Come, Higgins! You know what I mean. If I’m to be in this business I shall feel responsible for that girl. I hope it’s understood that no advantage is to be taken of her position.
In Act 2, Pickering directs these lines to Higgins, to make it clear he expects Higgins will not take advantage of Eliza over the course of their experiment. Pickering reveals here that he is an honorable character. Furthermore, his consideration for Eliza in this scene illustrates how, even before she becomes a lady, he cares for her as a human being.
You’ve never been broken in properly to the social routine. [Strolling over to the piano] I rather enjoy dipping into it occasionally myself: it makes me feel young again. Anyhow, it was a great success: an immense success. I was quite frightened once or twice because Eliza was doing it so well. You see, lots of the real people can’t do it at all: they’re such fools that they think style comes by nature to people in their position; and so they never learn. There’s always something professional about doing a thing superlatively well.
In Act 5, Pickering points out Higgins’ reluctance to participate in the social routine. Unlike Higgins, Pickering doesn’t mind the performative aspects of middle class society. Eliza’s performance was such a success, Pickering observes, that she seemed to be more a lady than those that were born into ladyhood. Pickering understands that being born into a position of wealth is taken for granted and considered a given. One’s identity, then, Pickering suggests, is not determined by nature, but by nurture.