I Drunk-Texted My Boss "I Love You" And He Replied Like A Gentleman
82% BELIEVED
CASE FILE #353
FILED: Apr 29, 2026
CLASSIFICATION: Funny & Embarrassing Stories
WITNESS ON RECORD: TwoDollarTess
JURY OF 206 READERS HEARD THIS CASE: 168 believed it, 17 had doubts, 21 weren't buying it.
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."
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."
THIS EXCERPT ENDS HERE. The remaining 141 words of the testimony — and the reader jury — are on file at:
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https://www.swearithappened.com/funny-embarrassing-stories/i-drunk-texted-my-boss-i-love-you-and-he-replied-like-a-gentleman-353/
Votes on record: 168 believed · 17 unsure · 21 didn't · 82% of readers believe this story