How To Get The Guy: The Grace Kelly Way

There’s a scene early on in Rear Window that lingers long after the credits roll: Jeff (played by Jimmy Stewart), recovering from a broken leg and a lifelong case of commitment-phobia, lays out all the reasons why he doesn’t want to marry his girlfriend Lisa (Grace Kelly). He tells his nurse with conviction, that Lisa Fremont, the refined, stunning, socialite, is not a good match for him, since his life as a rugged globe-trotting photographer is something she won’t be able to fit in with. She’s too polished. Too perfect. Too much.

And yet by the end of the film, he’s wrapped in her arms and ready to rethink everything.

What changed?

I had to rewatch the film to figure it out, and the second time around, I had pen and paper in hand, ready to take notes on Lisa's ability and particular gift to navigate a man’s cynicism. In my experience, men do tend to be more cynical than women (or maybe just more cynical than me?) So understanding whatever Lisa did stood out to me as crucial information and in that, Rear Window might just be the best piece of dating advice I’ve come across in years.

We’ve Forgotten the Art of the Female Pursuit

Modern dating advice for women tends to veer toward two extremes: Be a savage. Shoot your shot. Don’t wait for him. Ask him out. vs. Sit pretty. Wait. Don’t dare make a move. He has to do all the pursuing. 

It’s either aggression disguised as empowerment or passivity dressed up as “traditional values.” But somewhere between bossy and bashful, we’ve lost the third option—the artful female pursuit. The kind of pursuit that doesn’t chase or beg or demand. Lisa Fremont knew it. She never “chased” Jeff, but she didn’t sit idly by, either. She pursued him not by pushing but by inspiring, with an elegance and intelligence that most women today are too hesitant or too confused to try. Lisa proved Jeff’s cynicism wrong to the point that he had no option but to succumb to her. 

Modern dating advice for women is either aggression disguised as empowerment or passivity dressed up as “traditional values.”

Here’s what she did and why it worked.

1. She Entered His World

From the outset, Jeff doubts Lisa’s ability to adapt to his lifestyle. He’s out in deserts and war zones with a camera while she’s dining at 21 Club in custom dresses. He sees their relationship as incompatible, even doomed. The scene when Lisa is introduced depicts this tension clearly as Lisa comes in with a thousand dollar dress and dinner on a silver platter. For a bit she tries to convince Jeff to give up his kind of journalistic photography and get a job in her industry (fashion). She is inviting him to join her world and while this is sensible, Jeff knows he would not be satisfied going from shooting wild things to shooting pretty dresses. 

That was their demise, but Lisa did something about it. She steps into his world and in doing so, she shows him that she does fit in. 

When Jeff becomes obsessed with the idea that one of his neighbors has committed murder, Lisa could have dismissed it. Instead, she leans in. She gets curious. She listens. And eventually, she climbs into that world (quite literally) through windows and into danger, following the mystery with him. Still wearing pretty dresses, heels, and all.

She was the third person he had mentioned his suspicion to and the first to believe him and dive into the adventure with him. 

Lesson: In the female pursuit, one doesn’t argue or beg for a place in his world, we let our actions speak.

2. She Didn’t Manipulate, She Inspired

Initially, Jeff described Lisa as one of those “Park Ave fine creatures” but this notion was challenged when he saw her bravely facing danger as she breaks into the potential murderer’s apartment. This action challenged not who Lisa is, but who Jeff thought she was. This is crucial. Lisa never really changed for Jeff, she simply changed how he viewed her, and in doing so, she made a strong argument for their compatibility. 

Lisa never whines. Never guilt-trips. Never tries to trap Jeff into commitment. Instead, she gives him a vision. She paints the possibility of a life with her so vividly, so irresistibly, that he begins to want it for himself. She shows him how their world can come together without either one of them changing. This is key. She doesn’t seduce with neediness or ultimatums. She seduces with hope and beauty. 

Lisa didn’t convince Jeff with words, she showed him the dream and he liked it.

Lesson: Inspiration is not manipulation. One forces a decision on someone, the other gives them an offer they can’t refuse.  

3. She Encouraged Him When No One Else Did

In a story where almost everyone doubts Jeff’s sanity, Lisa takes him seriously. Even when she doesn’t fully believe him, she is open to hearing him out and looks into it. In doing so, she is showing genuine respect for his intelligence and instincts. At one point, she’s the only person who dares to take him seriously. That doesn’t make her weak or gullible; it makes her loyal, and that loyalty builds trust.

More than just believing; in listening to Jeff, Lisa made him feel seen, respected, and heard. That is a powerful aphrodisiac for any man and Lisa knew that. But she was not faking her interest. She already saw him, respected him, and listened to him, and once the potential murder mystery came to her attention she was as hooked into it as he was. 

Lesson: In a world where men are often dismissed, a woman who believes in them is powerful. Not blindly or foolishly, but discerningly.

4. She Challenged Him

Lisa wasn’t an always-yes-woman. She didn’t shrink herself to please Jeff. She never really stopped being that “Park Ave fine creature” as he first described her. In fact, she was quick to call him out when he was wrong, aloof, or unfair. When Jeff presented the reasons why he was not going to propose and he thought they should break-up, Lisa responded and held conversation for a bit, but when she realized that it wasn't moving forward, she walked away. 

When Jeff’s bluntness crossed the line into cruelty, Lisa didn’t miss a beat: “If your opinion is as rude as your manners, I don’t think I care to hear it.” And she walked away. 

She didn’t nag. She didn’t pick fights or play games. She made her points through action. She walked the walk, not just talked the talk. She showed him the layers of who she really was: resourceful, brave, intuitive.

She surprised him and that surprise is what cracked his walls.

Lesson: A good pursuit neither flatters a man nor it feeds its ego, it wakes him.

Now let’s clear something up.

Lisa was not a “pick-me” girl. She didn’t sacrifice her standards, she didn’t humiliate herself, and she didn’t mold herself into something unrecognizable just to keep Jeff around. She held onto her class, her style, her convictions, even her job which he thought was too far removed from his world. She was not one of those overly passive women who romanticize waiting forever without expectation. Lisa wasn’t waiting, she was working behind the scenes. She was involved, intentional, and emotionally intelligent.

There’s a cheeky moment in the closing scene when Lisa is reading an adventure book and when she realizes that Jeff is sleeping, she puts the book down and picks up Harper's Bazaar. This moment is telling because it shows that Lisa is picking up on his interests (and making sure he is aware of that), but she never gives up on her own. 

Lisa didn’t chase Jeff; instead, she moved towards him. There’s a big difference.

It would be a crime not to mention Grace Kelly’s wardrobe in Rear Window. Even if you haven’t seen the film, you’ve probably seen the dresses—flawless silhouettes paired with equally impeccable hair and makeup. But her wardrobe isn’t just a showcase of 1950s fashion; it’s a barometer for her relationship with Jeff. As their intimacy deepens, her outfits become increasingly casual, subtly reflecting the shift in their dynamic.

In the first scene, Lisa walks in wearing a stunning black and white dress: iconic, glamorous, almost untouchable. She’s all elegance, a woman from a world Jeff doesn’t think he belongs to. He even points out how expensive and overly refined it is, while Lisa simply enjoys it.

By the end of the film, after everything they’ve been through together, Lisa reappears in a casual button-down shirt, jeans, and loafers. Jeff is asleep beside her. The transformation is subtle but profound. She didn’t change, she’s adapted. She was willing to meet him in the middle, to build a future together. Her shift in clothes mirrors the shift in their dynamic. 

And that’s what real pursuit looks like: not abandoning yourself for love, but expanding yourself for it. That’s why real love makes us all better and more whole people. 

In a world full of women who are either shouting or shrinking, Lisa Fremont shows us another way: the lost art of the female pursuit. You don’t need to scream to be seen. You don’t need to corner a man into a relationship. And you certainly don’t need to pretend to be indifferent when you care deeply. You just need to be intentional.

Pursuit isn’t about proving worth. It’s about showing alignment.

It’s time we reclaimed the idea of the female pursuit. Not as a rejection of tradition, but as a celebration of women’s incredible intuitiveness and determination.