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The Secret Thoughts of a Literature Department Secretary: How I Went from Not Recognizing Workplace "Flirting" Signs to Becoming His Business Partner

The Secret Thoughts of a Literature Department Secretary: How I Went from Not Recognizing Workplace "Flirting" Signs to Becoming His Business Partner

icon-dateJuly 28, 2025
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My boss at work is intriguing. But I have no idea if there are any romantic feelings... As an arts major secretary, I ended up building a relationship with a business owner due to a certain trigger. I will secretly teach women tired of workplace romances a new way to meet people.

 

Table of Contents

 

1. “Is this a sign of interest...?” I was hoping just a little every day

I am a secretary in my 30s working in Tokyo.
You could say I'm not the sparkly “secretary” type, but rather an arts graduate who manages daily reports and schedules in a calm and understated manner.

There is an executive I am in charge of, and at first, it was just a business exchange, but one day I received a casual LINE message.

“You looked great in that dress today.”

I was unexpectedly moved.
But the next day, it returned to the usual “business exchanges.”

2. To become the girlfriend of a business owner, is “clarity” necessary?

Men in the workplace have a starting point for romance that is too unclear.

When invited to dinner, I can’t tell if it’s “as a subordinate” or “as a woman.”

Even if they are kind, it means nothing if it’s the same for everyone.

If I fall in love, it’s a loss. If discovered, it’s troublesome.

Moreover, if the other person is a business owner or an executive,
the image of the woman who becomes their girlfriend seems to be quite high, and I don’t feel like I fit that mold.

 

3. Reasons why I couldn’t be seen as a romantic interest

Plain, serious, stability-oriented.
In short, “good as a secretary, but weak as a romantic interest.”

Even at work, I often ended up being just “a convenient person,” and
there are very few experiences when I was seen properly as a woman.

 

4. One night, a person I met for the first time on

Somehow, I wanted to meet someone in a place that wasn't about romance.

Thus, I registered on .
At first, I thought, “Isn’t it just full of strange people?” but I was surprised to find many serious individuals.

Especially, the first person I met.
In their 40s, running a company. Their profile said, “I like polite people.”

While chatting on LINE,
they said, “I thought you must be working hard today, so I reached out,” and
I felt for the first time that my existence as “someone in someone’s shadow” at work was validated.

5. Love began not with a title, but with an atmosphere

After several meals together, our relationship gradually deepened.
There was never any talk about allowances or anything like that from him,
rather, he listened intently to my work stories and how I spend my days.

For the first time, I met someone who saw “me” instead of just a “secretary.”

 Conclusion: Rather than being swayed by signs of interest, choose a place that truly engages with you

Workplace romances are a battle with ambiguity.
There are far too many relationships where one expects the other to understand or notice without words.

However, in the outside world, there are people who will engage with you from the outset with the premise of romance or relationships.
I learned that through .

Similarly, for those who are “exhausted not knowing if there’s interest,”
I would recommend stepping out of the workplace for a while.

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