I Drunk-Texted My Boss "I Love You" And He Replied Like A Gentleman

Posted on Apr 29, 2026 by TwoDollarTess · 18302 views · ~2 min read

In one sentence: A tipsy birthday message goes to the wrong Derek, leaving one mortified employee facing the most awkward morning in operations.

It was meant for my sister. It went to Derek, 58, in operations, who has a moustache and a fishing boat.

I Drunk-Texted My Boss "I Love You" And He Replied Like A Gentleman
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It was my sister's birthday. I was four wines in and feeling emotional in the way that four wines makes you feel emotional, which is to say, professionally.

I typed: "I love you. You are the best thing in my life and I don't say it enough."

I sent it to Derek.

Derek is fifty-eight. Derek is in operations. Derek has a moustache that has been the same since 1994 and a fishing boat called Second Wind and a way of saying "morning" that makes you feel you have already let him down.

I saw the delivery receipt and I did the thing where your entire body becomes cold water.

I typed and deleted eleven messages. I considered leaving the country. I actually — and I am not proud of this — considered whether I could claim my phone had been stolen at exactly 22:41 by a very affectionate thief.

Derek replied at 07:02 the next morning.

He said:

"Morning. I think that was meant for someone else. If it was meant for me, I'm flattered but married. If it was meant for your sister, tell her happy birthday. Either way, the Henderson file is still due Thursday."

That is the greatest piece of writing I have ever received.

I went into the office and I could not look at him. He was completely normal. He said "morning". He said the thing about the Henderson file.

At about eleven, he came past my desk and put a coffee down and said, without stopping or looking at me: "My daughter did the same thing to her dentist."

And he kept walking.

I have never loved a man more in my life, and I still cannot look him in the eye, and it has been three years.

He retires in June. I have bought him a card. I have been writing it for six weeks and everything I put on it is either too much or nothing.

I will probably just write: "Thank you for the Henderson file."

He will know.
Drunk text conversation
Drunk text aftermath
Fishing boat Second Wind
Gentleman boss walking

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