Why Some Grand Gestures Feel Romantic — and Others Don’t

I want to compare two grand gesture scenes from pop culture to understand why one feels deeply romantic and the other doesn’t — even though, at first glance, the man appears to be doing the same thing to win a woman back.

The two scenes are Lloyd Dobler holding a boombox outside Diane’s window in Say Anything and Charlie Puth singing outside his ex’s window in Light Switch.

But there’s a reason that Lloyd’s is iconically romantic while Puth’s is not, beyond the fact that Puth’s is a fun parody of the same trope.

In Say Anything, Lloyd and Diane hear the song “In Your Eyes” on the radio after making love in his car. The lyrics, while romantic, become the song that accidentally attaches to that shared intimate moment between them.

Later, under pressure from her father, Diane pulls away from Lloyd. Without explanation, she ghosts him.

The modern meaning of “ghosting” is actually ironic because when Lloyd holds up his boombox, playing “In Your Eyes” outside her window, the song haunts her.

Even though she never acknowledges Lloyd’s gesture in that scene, she tosses and turns restlessly in her bed without coming outside.

What’s romantic about Lloyd’s gesture isn’t its size or boldness. It’s how badly he wants what he meant to her to haunt her mind, how badly he wants the connection they shared to be impossible for her to forget.

But then you look at Charlie Puth in Light Switch.

He gets in shape with his trainer. He cleans up his act. He rehearses. He prepares a bright, oversized “I’m sorry” sign, and he sings to the woman outside her window.

So much preparation and grandiosity goes into this compared to Lloyd’s gesture. Charlie has more intention, more effort, and more spectacle, yet the scene falls romantically flat.

Charlie even parodies the paradox himself. When the woman finally comes outside, she’s not moved. She’s already with someone else, a comparatively unpolished, almost slobbish-looking man. Charlie is left dumbfounded, which raises a question worth sitting with:

How can a moment built on so much effort feel unromantic — while Lloyd’s, which risks far more and prepares far less, endures as romantically iconic?

The common explanation today is that Charlie was acting needy and Lloyd was not. But that framing misses something important. Lloyd wasn’t carefully trying to appear non-needy. He wasn’t managing impressions at all.

In fact, if Lloyd followed modern advice to be “non-needy” to its logical conclusion, he would have done the opposite of what he did. He would have disappeared completely, giving Diane space to think. He would have stayed silent to avoid putting pressure on her to reciprocate his feelings.

At first glance, there are so many clear parallels between Lloyd and Charlie. Both gestures are grand. Both men are trying to reference a connection that once mattered. Both are showing up outside a woman’s window.

But the romantic resemblance starts to crumble when you look more closely: Charlie’s gesture is a literal musical performance for her. Lloyd’s boombox is not. Charlie is actively trying to be romantic by reenacting a familiar romantic trope from the 80s, hoping this strategy will work on her. Lloyd is not trying to look romantic at all. His head is not in strategy.

Charlie’s declaration is loud and public, designed so that everyone can see how he feels. Lloyd’s act is public, but its meaning is private. Only he and Diane know what the song signifies. Even though the spectacle is visible to the neighborhood, the memory itself belongs exclusively to them.

Also, Lloyd’s boombox is far away enough that it doesn’t come across as knocking on her door for a response. Meanwhile, Charlie is singing so close to her door that the only logical way to respond is for her to come outside. Charlie’s gesture demands acknowledgment. Lloyd’s leaves room for silence.

Lloyd wants the memory of their connection to exist peripherally, but meaningfully. He fully accepts that she may do nothing with it. He is not trying to convert remembrance into an obligation to talk to him.

Charlie, on the other hand, wants the memory of their time together not just to exist, but to act. He wants the memory to force engagement.

There is a reason that tree-etching is considered romantic, while graffiti is not.

Etching initials into a tree marks a moment in time in a way that outlasts the people who made it. The tree will keep growing, weathering the seasons, all while carrying the mark. The etching doesn’t demand attention from the tree—it simply remains.

Lloyd’s boombox works the same way. The song marks a moment they shared — that night they heard it together after making love. Just like the tree, no matter what Diane goes through afterward, no matter the season of her life she enters, that moment is etched in her remembrance. It simply exists.

Graffiti on the other hand is more like what Charlie did. It may be intricate and take real effort, but it isn’t made with time on its side. The artist knows it will likely be painted over or removed, so the mark has to demand attention now. It insists on being seen before it disappears.

That’s the difference. Charlie is trying to be impossible to ignore, while Lloyd only cares about being impossible to forget.

Romance blooms when being unforgettable doesn’t require being unavoidable.

Grand gestures become romantic when they let “us” haunt her mind without disturbing it.

The confusion around persistence comes from mistaking these two kinds of endurance for the same thing.

One kind of persistence is like initials etched into a tree. The mark is permanent enough to be unforgettable, yet quiet enough to be ignorable. It haunts the tree without disturbing it.
The tree keeps growing, season after season, carrying the mark.

The other kind of persistence is like graffiti — not meant to endure, but to insist.
One kind of persistence leaves a mark that can be ignored yet never forgotten. It haunts.
The other leaves a mark that must be noticed because it knows it won’t last. It disturbs.

Romance is about the desire to be impossible to forget without being impossible to ignore.