Milan Is Approved. The Man Is Pending.
A confidential file from True Louise
FILE 015 · YOUR FIRST CONFIDENTIAL FILE
An excerpt from Unedited, an autobiographical novel inspired by life.
There are moments in a woman’s life when an important decision requires careful analysis: financial implications, strategic objectives, risk assessment, and, occasionally, the opinion of the Flower Department.
This was one of those moments.
I had barely unpacked from Italy when an invitation to speak at a conference in Milan landed in my inbox.
Two days of talks and networking. If I extended the trip to five days, that would leave three entire days to myself.
I could wake up slowly, find a lovely café, order a cappuccino, people-watch, work remotely, and disappear into another Italian adventure.
This was beginning to look like a perfectly legitimate recharge retreat, practically a business expense. Another Italian workcation.
Then I remembered that gold-medal kiss.
Mr. Investment, the nice gentleman who had politely asked permission to hug me goodbye and somehow ended up kissing me passionately in the middle of the crowded street Tuesday lunch rush while innocent pedestrians navigated around us.
He lived in Venice. The conference was in Milan.
Different cities, admittedly, but the Flower Department had never considered geography a particularly persuasive obstacle.
Board Meeting
Motion before the Board:
Should Louise attend the conference, and contact Mr. Investment?
Head Quarter: “Yes to Milan. Two conference days followed by three days of remote work and recharging. A defensible allocation of resources.”
Heart Quarter: “Yes. Mr. Investment was lovely.”
Gut Quarter: “Go to Milan. Do not chase the Italian.”
Flower Department: “Yes to all of it. Finally, some Italian gardening on the schedule!”
“There is no schedule,” Head Quarter pointed out, and Flower considered this an administrative detail. At first glance, we appeared to have a majority. Until I noticed we had voted on two different decisions as though they were one.
Before anyone could untangle that, I was already wondering what I would write to him.
Like any sensible executive facing a communication dilemma in 2026, I turned to my trusted adviser. “ChatGPT… any suggestions?”
The obvious solution was simply to message him.
“I might be in Milan for a conference. Any chance our paths could cross again?”
Perfectly innocent, and casual. Except the intention wasn't. I knew exactly why I wanted to send it. I wanted to open the door to the Flower Department entering Venice for a second date, preferably over dinner. But I also wanted to know whether Mr. Investment would contact me after Italy because he genuinely wanted to see me again.
Or would he happily respond if I placed myself conveniently back into his inbox?
Those are not the same thing.
So I separated the two decisions.
Decision One: Milan
Would I want to spend time in Italy even if Mr. Investment had never existed?
Absolutely.
Approved on its own merits.
Decision Two: Mr. Investment
Would I like to resume that street kiss?
Also one hundred percent yes.
But that was not currently the question. The question was whether Mr. Investment would take initiative without receiving a strategically placed reminder that I existed.
Pending, no action required.
This was deeply irritating to the Flower Department. She had already mentally booked her train ticket to Venice. Head Quarter called her behavior premature capital allocation.
Eventually, the Chairwoman called for order. The conference was approved. Contacting Mr. Investment was not, yet.
Somewhere on my WhatsApp sat a perfectly innocent draft:
“I might be in Milan for a conference. Any chance our paths could cross again?”
I placed my phone facing down.
Flower objected.
Motion denied.
Your turn at the table
Would you send the message, or leave the phone facedown?