We never meet the real Madeleine at all in the movie, so like Scottie, we only get to see an idealized fantasy. Madeleine as played by Judy is elegant, regal, and refined. She’s alluring and sensual without being licentious or otherwise undignified. She’s mysterious and worthy of examination, especially to a detective. She’s a unique mixture of the distant femme fatale as well as the adorable damsel in distress. In short, Madeleine is the ultimate dream girl for most men.
Where Scottie is in many ways the everyman for male viewers to project their experiences onto, and Judy fulfills the same role for women, I believe Madeleine is more of a larger than life metaphor. She is the fantasy of sex and fulfillment which our modern society bombards us with 24/7. This image is fed to us through advertisements, melodramatic love songs and romantic films which give people the wrong expectations of what courtship is actually like. Women are told they’re not beautiful unless they buy XYZ product or ABC designer dress. Men are told the reason they’re having problems getting women is that they don’t drive the right car or drink the right beer, and if they just buy more products, suddenly they’ll be irresistible. It’s these warped expectations of the beholders which exacerbate a lot of the insecurity and dysfunction in people today. This is represented in the film by Madeleine’s legacy destroying Scottie and Judy’s lives.
How Much of Madeleine is Real?
Part of the fun of Madeleine’s character on rewatches is determining how much of her dialogue and mannerisms were Gavin’s instructions and how much was Judy improvising and/or fighting back attraction for Scottie. On some level I think Gavin intended her to be someone Scottie would love to follow around and learn more about. At the same time though, I don’t believe Gavin intended for him to actually fall in love and get so tortured by the experience. It’s obvious some kind of meeting between Madeleine and Scottie was planned, as Gavin would want Scottie to see that these travels of hers were unconscious. The only surefire way to communicate as much would be for them to talk face to face. Later, after the two meet up when she delivers the letter and they go to the Sequoias, Scottie is allowed to witness her going into an apparent fit of apparition. Finally, on the beach and back in his apartment Scottie hears about her dreams and supposed prophecy of doom.
At the same time, it should be noted that while hearing Madeleine describe her own condition could aid the plan, Gavin could also have achieved his goal of murder if Scottie had still been trailing her from afar if she had just visited the mission on her own. Indeed, having Scottie interact with and imprint on Madeleine seems pointlessly cruel and potentially problematic. What if Judy flubs, gets caught in a lie or breaks character? What if Scottie refused to let her go into the church after their kiss? Or Scottie rose above the call of duty and staked out the Elster home in case Madeleine had another fit of apparition at night? (He might have seen Judy or Gavin himself breaking character in that scenario.)
So, all of these meetings could have been part of a carefully laid out scheme by Gavin, or it might have been improvisation when Scottie acted in a way that was unexpected. It would be far more wise to assume Scottie would have taken Madeleine to a hospital or back to her home after her first suicide attempt in the bay. Having the two get involved seems very needlessly risky for Gavin and with no apparent benefit to his plan. Scottie seemed very visibly convinced that Madeleine knew nothing of Carlotta and was therefore in some sort of trance in his second meeting with Gavin (before talking with Madeleine herself). Nothing Madeleine says in Scottie’s apartment is new information, it’s just getting it from the horse’s mouth so to speak.
This is why, in my opinion, the events in Scottie’s apartment were unforeseen and therefore Judy was improvising (and very well) while trying to remain in-character. This is the reason she insists on tying up her hair so quickly—to feel like Madeleine—and why she leaves at the first opportunity. After all, the longer she remains the greater the risk she gives herself away. So, the Sequoia forest, beach and Scottie’s apartment were her and Gavin trying to work the shifting situation to their advantage, and required a lot of further improvising by Judy. This is why she says “it wasn’t supposed to happen this way—it shouldn’t have happened!” at the Spanish Mission. She did not originally intend to lead this poor guy on so much, to make him so personally involved in Madeleine’s plight, and to fall in love with him. The original plan was far more impersonal.
I believe the moment Judy (as Madeleine) fell in love, and where her in-character improvisation got carried away, was when they kiss on the beach. If the ocean represents Gavin and his influence (more on this later), the splash from a wave represents a snag in his plan as it came up against this unforeseen circumstance. Judy was so wrapped up in the role of damsel in distress, so empowered by having a man fawn over her, that she acted without considering the consequences. Not to mention, in-character it makes sense for Madeleine to throw herself at Scottie in this scene of vulnerability and passion, so Judy got caught up in the moment and did just that. Like Scottie pulling her out of the bay, this willful and complete submission may have awakened some primal feminine role in her. I like to think having a man care for her, take such an interest in her, made the plain ordinary Judy feel like a desirable woman for the first (second maybe, including Gavin when he led her on) time in her life.
An Amalgamation of Two Conspirators
Gavin either married the real Madeleine for the money outright, or he actually did love her once. If the latter, it means she displeased him after he felt constrained by the shipbuilding businesses he was forced to take over and then threw her away, another continuation of the Carlotta story. There’s not enough evidence to say, but I prefer to believe the latter as it better mirrors Scottie’s arc and the Carlotta legacy. Assuming the real woman was anything like Judy’s portrayal, this implies that even the perfect, photo-shopped feminine ideal doesn’t stand up to scrutiny when held up close.
For Judy too, I strongly suspect she enjoyed playing the part and perhaps getting closer to Scottie as discussed in the previous subheading was her impulse because it would allow her to go deeper into this character. After all, Madeleine is everything plain-Jane Judy is not. While Judy’s distressed by it, and largely motivated by guilt towards Scottie, I also suspect part of her willingness to become Madeleine again in the second half is because on some level, she wants to assume those characteristics again.
Madeleine’s final lines on the tower are the only time she has ever been truthful to Scottie (Except maybe when she said she enjoyed talking to him earlier. And perhaps some of that improv at Scottie’s apartment regarding falling into water while “leaping from one stone to another” might have been based on real anecdotes.)
the Carbon Freeze 
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