Tris' Thoughts

In part 1 , I introduced the premise and overall story of the 2001 film Kate & Leopold, with focus on the character of Leopold, played by Hugh Jackman. But here, we’re going to discuss the second half of the story: Kate McKay, played by Meg Ryan. Please view part 1 before reading this for further context.

Definitely Not Shop Girl

For those who have seen 1998’s You’ve Got Mail, you may notice a few similarities and a lot of differences between Kathleen Kelly–the cute, underdog bookstore owner–and Kate McKay–the ruthless executive. Not to go on too long of a tangent, but I find it fascinating how both characters are named Kate, and with some narrative tweaking, one could even treat Kate & Leopold as a “bad ending” future You’ve Got Mail. You’ve Got Mail sees Kathleen having lost her business, forced to move on as she pursues a romance with the big business executive who put her out of business in the first place. Stretch the timeline, and one could imagine that Kathleen becomes a jaded executive herself, having experienced professional and romantic disappointments.

I start this section with that little bit of fan-fiction because unlike Leopold’s character, Kate McKay is not directly explained. We know that Leo’s parents died and he’s been raised by his uncle. We know what’s led to his personal struggles. We get enough insight into his past to form a strong idea. We don’t know the context of his parents’ death, but the most important details are present. We don’t get the same for Kate. But this pushes the audience to connect the pieces more.

Kate & Leopold has a director’s cut, so there are two opening scenes for Kate to choose from. The director’s cut starts with the ending of some romance movie being played in a theater. The leads are in an intimate embrace just before we see a horse-drawn carriage as typical romantic music plays. We see Kate’s secretary, Darci–played by Natasha Lyonne–is absolutely enthralled by the film. But Kate is not.

Kate is part of the test screening team. And she looks put-off by–even bored with–the film, to the point where she leaves the theater temporarily, and returns when it’s time to gauge the quality. Kate doesn’t like the female lead, and her colleagues agree with her. The audience isn’t testing great with the movie either, and the director is insulted. He defends his film as being real. He defends the female lead as being likeable because she’s made mistakes (with the implication being she cheats on the movie’s male lead at one point).

The director accuses Kate of sucking the life out of cinema, and this bothers Kate. On the drive home, she vents about how it’s just her job to gauge what audiences like and translate that into profits. She dismisses the director as a dreamer, contrasting with her realist sensibilities.

Cold, but professional, the scene could have ended there. But there’s more to it. Kate starts talking about how she dated a dreamer (Stuart, played by Liev Schreiber) for 4 years, having to pay his rent because he was unemployed. Kate is disillusioned. She’s biased. She’s annoyed by people who prattle about the heart, dreams, and other pathos formats. As she puts it…

“I don’t care if it’s crass, give me the numbers, give me the bottom line, give me the truth straight up, no chaser.”

Kate is fed up with people who value feelings over reality. The audience was not resonating with the director’s film. Kate and her associates hadn’t published a single discouraging comment, nor did they influence the audience. But the director attacked Kate and her colleagues specifically just because they didn’t like his character. Instead of taking responsibility–instead of recognizing that the layman didn’t care for his film–the director goes after the easy target: the cold executive, who is just translating the data.

And what I find quite fascinating is that the heavy implication is that Kate personally dislikes the director’s female lead because she did something morally wrong. Kate leaves the theater after the leads embrace. Kate & Leopold doesn’t outright state that Stuart cheated on Kate (though their first scene together may imply it), but it is clear that Stuart failed the relationship.

When you look at all of Kate’s actions in this film, she never commits any crime or sin as socially repulsive as cheating on her partner. It’s easy to treat her as a bad person because she’s mean and cynical. But actions speak louder than words, and Kate’s actions throughout the film are sacrificial. Kate doesn’t like liars. Kate doesn’t like irresponsible people who don’t carry their own weight. She gets vilified for pragmatism, and this makes her gradually more willing to act less honestly later in the film.

Those Were Your Best?

After Kate returns from the theater, she discovers her ex, Stuart, bringing Leo’s unconscious body into his apartment. Kate calls Stuart to ask for her palm pilot back, and Stuart can’t deal with that because he has the Leopold situation.

Let’s get in Kate’s head. She is fresh off that terrible experience at the theater. She has Stuart on the mind. They recently broke up. Kate sees Stuart with a body. She thinks he’s already sleeping around with someone else. He’s completely in his right to, but it’s typically frowned upon to start dating so early after a breakup. And Kate’s reaction tells us that she feels insulted (and that will be very clear as we go over more of the scene).

But Kate doesn’t open with accusing Stuart. She starts by wanting her palm pilot back. She’s fishing for information: trying to naturally get Stuart to drop clues. But there’s sincerity in her request. It’s symbolic that Stuart still has Kate’s palm pilot. Kate left it and didn’t go back for it. Stuart has neglected to return it. There is a lingering relationship between the two, with neither having fully committed to severing ties. And there’s additional symbolism in how Stuart isn’t being responsible in returning Kate’s things. And both parts of the symbolism show up in Kate having the shock remote for Stuart’s dog, Bart. One could even imply this is a bit of hypocrisy on Kate’s part.

Kate calls Stuart out for bringing a woman home, and Stuart goes out of his way to clarify it’s a man and that he’s not getting laid. This doesn’t necessarily convince Kate, as she’ll later claim that she doesn’t care what Stuart is doing (or who he’s doing) when clearly, she does. But Stuart transitions the topic with a very poor choice of words

“Something big is happening: something that validates my entire life.”

The way Kate sarcastically placates Stuart as he talks about finding a time portal says everything. Stuart tells Kate that she never supported him. He mentions how he told Kate about Leopold from history. He’s leveraging that she never took his passions seriously. But Kate insists that she did believe in Stuart and was burnt because of it. Kate had to monetarily support Stuart while he pursued his dreams: dreams which would be seen as insane by any normal person. Once more, they were dating for 4 years. That’s at least 4 years of putting up with Stuart’s behavior.

When Stuart says this whole thing validates his life, it sounds like a gambler talking about how he’s about to make it big. And Kate has to put up with it. But Stuart goes further. He makes up a story about Leo being a hacker who passed out on his couch after going out for drinks. And he agitatedly asks if that’s enough for Kate and her “little focus group”.

In fairness to Stuart, he’s got a lot on his mind in this scene. It’s 1 AM, he’s got an accidentally kidnapped ancestor on his couch. And his ex-girlfriend is chastising him over the phone. Everything he’s been working toward is finally paying off, and the one person he trusts enough to tell the truth to doesn’t believe him. It’s very possible that Kate had taken him seriously years ago, but not anymore. Stuart is upset at being treated like a joke. So he lashes out at Kate’s profession: demonstrating a lack of foresight and awareness.

Kate gives one of the sadder lines in the film in response:

“You know what, Stuart? I blew my best years on you.”

to which Stuart responds, “Those were your best?”

Kate is crushed. And all Stuart can manage is a passive apology before hanging up. Kate believes her best years are behind her, and while her comment is harsh in its own way, it’s in-part her attempt to reach Stuart: to make him understand the time, emotion, and money she puts into him. And Stuart throws it back in her face, implying that it wasn’t even that good. It’s pretty cold to say that to the woman who paid your rent for years.

Enjoying Leopold

One of the scumbags of the film–J.J. Camden, played by Bradley Whitford–treats Kate as a sexual conquest. He says something incredibly discouraging about how she’s like a man who understands women, and that she doesn’t “do pretty”. Kate puts up with this because J.J. is her boss. In fact, she puts up with a lot of inappropriate behavior from J.J. for the sake of advancing her career. But J.J.’s words are basically a rephrasing of Stuart’s snarky remark: “Those were your best?”

Going back to Leo’s description for Kate when they properly meet, Leopold starts by calling Kate’s attire plain, but immediately goes on to accurately guess her career and compliment her for it. Leo doesn’t just flatter Kate, he expresses genuine admiration for her pursuits as a woman. This instantly contrasts the other men, none of which show much appreciation for her work.

That isn’t to say things progress well at first.

This scene is incredibly important. Kate isn’t actually upset with Leopold. Let’s set the stage. Charlie (played by Breckin Meyer) has just gotten back from some acting pursuit trip. He befriends Leo, invites him to dinner, and Kate tolerates this. Charlie is Kate’s younger brother, living in her apartment. Charlie is never shown being employed. For all intents and purposes, Charlie is another disappointment in Kate’s life: a dreamer who isn’t actually making something of himself and supporting himself.

At this point, Kate’s opinion of Leopold is mixed. He acts strange and might be crazy (thinking he’s a duke from the 19th Century), but he’s polite, considerate, and supportive. The problem is, Leo spends this dinner scene bringing up Stuart. Worse, he talks about two very sensitive topics he doesn’t know at the time are sensitive. He assumes Kate and Stuart were engaged–which Kate quickly clarifies they weren’t even close to that–and then he starts talking about the time travel portal.

Kate tolerates the discussion at first. She even says, “But I did read his papers, however, to show support.” [0:20 – 0:23] Immediately, this shows that Kate genuinely supported Stuart in spite of him being a freeloader. Whether or not she took the papers seriously, she went through them.

As Leo gets going on Stuart’s findings, Kate has to excuse herself. She’s reliving all those years of putting up with Stuart. And then Charlie remarks at how amazing Leo’s “performance” is (as Charlie believes Leo is just acting). And Kate snaps.

“Oh, stop it, please! No more! Stop, please. I beg you. I’m tired. Can you go away? Can you just go away? Can you go away?” [1:00 – 1:07]

Charlie tries to dismiss Kate’s behavior as her just being drunk. He’s appalled at her behavior. Leo is distraught and confused. But Kate isn’t having it. She tells Charlie to shut up, and keeps urging Leo to leave.

As Leo leaves, Charlie demands an explanation from Kate. Kate passively dismisses the situation, pointing out how crazy Leo seems. Charlie doesn’t recognize the underlying issues. He’s too entertained by Leo to notice. And when Kate makes a passive jab about what show Leo might be acting for, Charlie takes it personally.

“You know that just because someone doesn’t have a paying gig, it doesn’t mean they aren’t working on their craft!” [1:39 – 1:45]

Charlie is vocalizing the same insecurity that Stuart is: working toward something but not actually making money from it. Leopold shares this insecurity, as he has to marry for money rather than pursue his passions. And in a symbolic gesture, Kate starts lighting a cigarette, only for Charlie to swipe it from her.

Here, Kate is using a coping mechanism. First it was the wine. Now it’s the cigarette. It isn’t healthy for her, but she’s tired, and she wants some kind of escape. But her dependent brother takes that from her while expressing his own problems without truly trying to understand why Kate is so upset. When he says “She’s drunk”, he’s saying that she’s acting irrational and unprovoked. And while it was rude of Kate to act how she did, and Leopold did nothing knowingly wrong, there are clear reasons for her behavior.

A Hero at Kate’s Expense

Leopold ingratiates Kate by being useful to her. After an argument over toast, Kate decides to take Leopold to audition for a commercial for Farmer’s Bounty margarine. Kate is taking advantage of Leo here, but not in a predatory way. Keep in mind, Kate does not believe yet that Leo is actually a 19th Century duke. She doesn’t feel the need to explain how everything works. She assumes he understands, and she isn’t tricking Leo. He’s coming with her willingly. And we see later that he understands the context of what he’s doing: performing for an advertisement.

The audition is quite successful, and Kate’s boss, J.J. invites her to dinner to celebrate.

Kate’s behavior is very telling. She doesn’t rebuff J.J.’s advances even though they’re highly inappropriate. And she starts celebrating loudly as she and Leo walk down the street. Why? Because Kate is getting what she thinks she wants. She’s worked extremely hard. She wants her promotion. She wants the prestige. She wants the accomplishment she labored for. She’s been disadvantaged by other people, so she doesn’t even appear to register that her boss is a predator. She puts that thought away and celebrates what she can.

Kate even goes out of her way to praise Leo’s performance. She tells him he’ll be on national television. She’s happy for him. He did the work. He earned the reward. Kate doesn’t have to share the glory with him. She chooses to give him credit because that’s who she is at her core. Leo got results, and Kate is all about results.

Leopold picks up on the predatory intentions J.J. has, and offers to chaperone Kate. But Kate dismisses this. She wants to enjoy the moment, and gets slightly annoyed when Leo keeps talking about the matter. Kate feels like she can handle the situation on her own. And to a degree, she’s right. But there’s a stark contrast between how Kate acts around subordinates and equals versus J.J.: her boss. She’s submissive, timid, and nervous. She doesn’t talk back when he says something inconsiderate because she feels powerless. She doesn’t want to lose her chance, and she’s willing to degrade herself for it.

One might see Leo’s performance at the dinner scene as heroic. To a degree, it is. He is standing up for Kate’s honor, and his intentions are very much to help her. But just like J.J., Leopold is not honoring Kate’s agency. The dinner between J.J. and Kate is private. And while J.J. is being a slimeball, Kate made it clear that she didn’t want Leo to interfere. But Leo and Charlie insert themselves into the evening.

Leo puts J.J. in his place, partly for Kate’s sake, but also to assert dominance and superiority. And what Leo doesn’t recognize is that he is jeopardizing Kate’s career opportunity. Kate pushes back and tries to move things away from the uncivil segments, but Leo mouths off at J.J. before leaving.

Kate got herself into this mess. But Kate is responsible enough to recognize that she has to get herself out. It was wrong to agree to J.J.’s dinner. And if Kate had chosen to rebuff J.J. at any point, that would have been the right call. But by doing it for her, Leopold is taking away her choice.

But the difference? Leo owns up.

There isn’t much in Leo’s letter but it hits the right points. He admits to acting like an idiot and being prideful. He admits that he’s interested in Kate romantically. And he invites her to dinner. This reaches Kate because Leo is taking responsibility. And while it takes some greater urging for her to go through with it, the two have dinner.

Kate admits that she has a bad track record with men: specifically saying that she’s not good with them. This is an extremely sad moment because Kate could easily say something mean about men. She has every reason to. Her brother, her ex, her boss, even her father potentially–after all, she mentions her mom but not her dad–all fail her. She could go on a tirade, calling all men pigs.

She doesn’t. Kate blames herself. And it’s heartbreaking. Kate doesn’t like herself. But the thing is, Leo does.

Leo doesn’t let Kate clean the dishes. He offers her a dance. He offers her a fantastical romance. And Kate is reluctant. She doesn’t know if she can “leap”. She’s been burned many times and doesn’t want to go through that again. But she gives it a try anyway, because Leopold seems like a genuinely considerate and responsible person: something Kate desperately values.

The Contrast

Kate and Leopold share more time together. They learn more about each other… and then it’s time to film the official commercial. Leopold is appalled by the Farmer’s Bounty food he’s eating. Not only does it taste terrible, but he considers it dishonest to advertise and promote it while pretending it’s great. So he storms out, and Kate has to go after him.

Leo confirms that Kate has tasted Farmer’s Bounty, that she agrees it tastes terrible, and that she’s okay with getting him to promote it. In her words: “It’s diet! It’s supposed to be awful.” [0:31 – 0:34] She’s trying to keep things somewhat lighthearted, but Leopold isn’t having it.

So Kate tries to make him understand that the stakes are high for her, but before she can even finish her sentence, Leopold cuts her off: saying that they can both just walk away from the commercial. For Kate, it’s a very small thing with big repercussions. She doesn’t see the advertisement–lying by omission to Leopold for the advertisement–as a bad thing because she’s used to that kind of deception in ads. But if she doesn’t make this small thing work, she could be in big trouble.

In contrast, Leopold thinks it’s a very small thing to refuse to do the advertisement out of moral obligation. The moral outrage is the big part for him, in part because he doesn’t have to deal with the consequences. And he talked over Kate while she was trying to tell him how much of a risk he’s putting her in. It was wrong for her not to make sure Leopold didn’t know what he was getting into, but it’s also wrong for Leopold to downplay and dismiss her.

This scene is very powerful… and it’s all over margarine. Both characters have very strong points. And while Leopold has the moral high ground of deceptive advertising being wrong, Kate has the moral high ground of fulfilling one’s responsibilities. And while Leopold is terse and hostile, Kate tries repeatedly to remain civil. She says “[…] Sometimes, you have to do things that you don’t like. Sometimes, you have to suck it up and finish what you’ve started; it’s part of life.” [0:54 – 1:00]

Leo doesn’t even combat this point. He just says that Kate sounds like his uncle, which is telling. Leo’s uncle isn’t a bad person. He pushes Leo to do things Leo doesn’t like for Leo’s own sake. And despite Leopold dismissing Kate’s point, she goes from confrontational to pleading.

“Look, Leopold , Jansen Foods is a very important account for my company. If you don’t go back in there, then I get into a lot of trouble.”

To which Leopold ignores because he’s stuck in his own moral outrage. “Is this what you do at work, Kate: research methods to deceive people? Refine lines until they resemble truth? It’s no wonder you dread your work week.” [1:03 – 1:20]

In fairness to Leopold, it sounds to me at least like he’s intentionally avoiding blaming Kate. It sounds like he’s trying to advocate for why she should leave her job because she hates it. But he isn’t engaging with what she’s saying. And she isn’t engaging much with what he’s saying either.

And this leads to the crux and climax of their contrasts as characters. Kate calls out Leopold for being pious and not having to work. Leopold rightly tells Kate that she doesn’t know what he’s done with his life, but Kate has a sharp retort ready.

“And you have NO idea what I’ve done with mine! i haven’t had all that many comforts and conveniences, Leopold, because I’ve been paying dues ALL my life. And I’m tired, and I need a rest, and if I have to peddle a little pond scum to one, then so bit it.” [1:36 – 1:53]

Leopold isn’t happy about this, but he goes back and finishes the commercial anyway. At the end of the day, these are two different people who have suffered differently, with some similarities. Leopold’s uncle has a very appropriate line, describing men who made themselves from nothing, while Leopold was born with everything, and from it, fashioned nothing. Just like Charlie, and just like Stuart, Leopold hasn’t yet accomplished what he wants. He’s considerate. He’s noble. He’s gentlemanly. He’s even moral. But he hasn’t struggled.

Kate has struggled. She’s supported her brother, her ex-boyfriend, her company, and more. She’s been trained to dress “plain” and look “not like a woman” by the people around her. She’s been raised to think it’s okay to be deceptive to get what you want in spite of not liking dishonesty. Leo has the luxury of moral outrage because he hasn’t been challenged. Kate has bent to immoral behavior because she’s been challenged.

All this screams someone who had to grow up far too quickly. It’s very likely that Kate’s father wasn’t around much, or even that both parents were absent at some point. But even if she had stellar parents, she’s been the parent to her brother for far too long. And here’s another person in Leopold, who is tearing down what she perceives as her dream.

Should They Be Together?

By the end of the movie, Kate and Leopold get back together: with Kate choosing to live with Leopold in his time. She’s leaving a successful career and her family, to live with a man who is going to lose his income if he doesn’t marry into money. So why do they get together in the end? Because they’re both right. And they both admire each other.

Leopold is right about ideals. One should marry for love. Pursuing invention and progress is great. He has a strong sense of honor and morality.

Kate is right about life. You have to be responsible. You have to deal with your problems and not run from them. You can’t rely on others to constantly lift you up.

Kate is an experienced business woman. Leopold is an educated inventor. By all metrics, that’s quite the combination for success. The 1800s is a different time, but Kate has the ingenuity to be a capable business entity. And she could even do so through Leopold. Leopold’s inventions are provably revolutionary, and would turn a profit. Working together, they’d likely do fine economically. But even if they didn’t, the point is that they’d be together. Leopold won’t die if he loses all his money. Kate has already given up her career. At the end of the day, the characters teach a lesson for each other.

Kate thought she wanted prestige. And it’s completely fine that she continue to pursue that. But not at the expense of her integrity and honor. She was losing parts of herself with her life choices. She wasn’t happy. And even with the job success, she probably wouldn’t have stayed happy.

Leopold was living a passive life. He wasn’t being responsible. He needed to make tough decisions, and with Kate in his life, he has someone willing to help him while also holding him accountable to pull his weight.

I won’t get into the time travel aspects because that’s a mess in most time travel stories. But the great thing about Kate & Leopold is that the message remains even if no time travel was involved. These are two people who compliment each other. They hold each other up and accountable, and save each other from mutually unhappy lives.

Sources

Kate & Leopold. Directed by James Mangold, Miramax Films, 25 Dec. 2001.

‌“YouTube.” YouTube, 2025, http://www.youtube.com/.