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Miss Overthinking and the Man Who Mistook Silence for Cool

At twenty-five, she had reached that awkward age when you no longer felt entitled to call yourself recklessly young, yet were nowhere near old enough to sigh about fading beauty. And still, she was single. Very single.

Whenever she looked back on the handful of romantic episodes in her life—if unreturned crushes could even be counted as romance—she felt a fresh wave of indignation. She was, by any reasonable standard, a perfectly normal young woman: pleasant face, healthy limbs, a waist where a waist should be, curves where curves should be. So how had she somehow remained unattached for twenty-five whole years?

Meanwhile, the women around her seemed to move through love as if it were a compulsory course in life. They dated one boyfriend after another, had their hearts broken, made scenes, slept with the wrong people, survived breakups, and after all that chaos somehow each found her place in the grand emotional order of the world. Everyone else’s youth seemed to blaze. Hers, by comparison, felt dim and uneventful.

The more she thought about it, the angrier she got. The angrier she got, the more determined she became. On a sudden impulse, she emptied out an entire drawer of diaries—everything from primary school through her working years—and decided she would find proof that someone, somewhere, had once loved her.

The moment she opened them, lost memories came rushing back.

The first mistake

In middle school, she had a crush on a boy in her class. For two months they exchanged looks that felt meaningful, those subtle glances that seemed to contain entire conversations. She was convinced the signals were strong enough. Surely he liked her too. Secretly pleased with herself, she waited for the confession she felt was only a matter of time.

Then gossip began circulating through class: he had some old romantic history with the beauty from the class next door, some vague unfinished business from primary school, the kind of rumor that sounded suspiciously like lingering feelings and loose ends never tied.

She hated hearing it. But he had never actually said he liked her, and she was too proud—and too embarrassed—to say anything first. So whatever had been forming between them slowly faded into nothing, worn down by hearsay and hesitation.

She stayed bitter about it for a long time. Her first crush ended not with heartbreak exactly, but with a furious scolding directed at herself.

Serves you right for reading too much into things. If a boy really liked you, would he make you wait that long?

Right then, she made herself a promise: never again would she get carried away and celebrate before anything had actually happened.

The second time she should have known better

But girls with bad memories rarely avoid old mistakes for long.

By her second year of high school, she had already forgotten the lesson and fallen for the athletic captain from the class next door.

Love always seemed to play the same trick on her. The moment she liked someone, he was suddenly everywhere. Every ordinary encounter took on the glow of destiny. Every accidental crossing of paths became, in her mind, a deliberate arrangement by heaven.

And worse than that, she was sure he liked her too.

If he didn’t like me, why did he smile at me like that? If he didn’t like me, why did he turn around to look at me? And for God’s sake, if he didn’t like me, why did he even know my name?

After delivering this perfectly persuasive speech to herself, she felt absurdly confident about the whole thing. For a while, her dreams each night followed the same script: he would confess, and everything would finally make sense.

Of course, fantasies are fragile things.

One evening, she saw with her own eyes the athletic captain walking hand in hand with the school beauty. She trailed behind them in silence for an entire stretch of road before finally running home with red eyes and crying for hours.

Third time’s not the charm

For all her tendency to brood and to fall hard, she considered herself a woman of principle. And her principle was simple:

Never more than three times.

She would allow herself one last sincere crush. If that failed too, then she would swear off taking the initiative forever.

But life does not hand out victories as compensation for past defeats.

The third time ended no better than the others. The boy she liked took another girl’s hand as they were leaving a movie theater, and that was enough. After her third romantic failure, she began to doubt not just her luck, but herself.

Maybe boys just don’t like me.

It was the kind of thought that starts as self-pity and hardens slowly into resignation.

So the years passed. She never again met a man who truly stirred her heart. Little by little she gave up expecting anything different. Perhaps, she thought, life would simply go on like this.

Then came the man who looked cold because he was afraid

At some point, even heaven seemed to find her pessimism a bit excessive.

And so into her life walked a man who looked, at first glance, almost offensively composed.

One night, he stepped into a late-night screening. It was one in the morning. The theater was nearly empty, scattered with only a few couples. In the last row, tucked into a corner, sat a lone woman with a box of popcorn, quietly waiting for the film to begin.

He walked over as if compelled by something he didn’t understand.

Without saying a word, he sat down beside her.

She turned to look at him, startled. He simply smiled, still saying nothing. Then the lights dimmed, and the movie began.

Neither of them paid much attention to it.

She kept sneaking glances at the man beside her, certain there was something strangely familiar about him, yet too wary to trust the feeling.

Why sit next to me when there are so many empty seats?

Could he be someone who once had a crush on me?

No. Don’t start imagining things again.

Beside her, the supposedly cold and unreadable man was fighting his own battle. In his head he had rehearsed at least ten different opening lines for after the movie. In the end, he couldn’t wait that long.

Before the film was even over, he turned toward her and leaned in.

“Sorry,” he said, “but I have a story I can’t help wanting to tell you. You can keep watching while I talk. That’s fine. Ahem... here goes.

“L was a boy who seemed distant and wasn’t very good at expressing himself. In middle school, he fell for a girl in his class named Z. Z was bright, lively, always smiling—like a sunflower. He spent a long time thinking about how to confess to her, and he had the feeling she liked him too.

“Just when L had finally worked up the courage and was ready to say something, rumors started spreading—nobody knew from where—that he had something going on with a girl named W from the class next door. Z seemed to care about those rumors. She became colder and colder toward him. L wanted to explain, but he was afraid it would only make things worse, so he chose silence.

“And that was how they drifted apart.

“It took L many years to understand that what had looked like coldness in his youth was really just cowardice wearing a mask. The truth was, he had no confidence he could ever deserve a girl like Z. But if he were ever lucky enough to meet her again, he would be braver this time. More direct. Because over the years he has learned something simple: even failure is better than regret. Don’t you think?”

By the time the movie ended, Miss Overthinking was in tears.