Some of the worst things I've ever said

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Have you ever said something that came out wrong, or was so inappropriate that you were embarrassed years later?

I'd like to claim that it's the Coyote medicine that occasionally causes me to say the worst thing imaginable without even trying. But most likely it's because my brain sometimes engages the language function without the thinking or tact function.

Here are some of the things I've said that I regret the most:

Things where I meant to say one thing, but somehow said another.

To a female friend

What I think I _meant_ to say:*
If I were straight, I would have slept with you anytime.
(We'd been discussing the young lady's high libido and joyful unrepentant approach to sexuality)

What came out of my mouth:
I could have slept with you anytime.

Which is probably one of the most disrespectful things I could possibly have said, on so many levels, that sometimes, I actually wake up in the middle of the night, horrified that those words actually came out of my mouth and went into anyone's ears, much less someone who I consider practically a goddess.

*I'm not entirely sure what was going through my mind (which was in a disorganized state at the time)... what I said was so utterly unlike anything that I would even think of, much less say, that I can't even begin to explain it or entirely fathom it.

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To a friend who was grieving after the loss of a beloved grandparent, and who remarked that the thing that made it all so hard to deal with was that "it all happened so quickly."

What I _meant_ to say (two separate things):
A: It was better for him, perhaps, that his death was not lingering and slow.
B: You would have wanted what was best for him, wouldn't you?

What came out of my mouth:
A+B Combined: "What would you want him to die slow?"

Things where I just blurted out something without really considering the impact or appropriateness

The situation:
I met a friend I had not seen in years, at a public party-style event, which included an art gallery. The friend had apparently just taken a powerful hallucinogen that they were unfamiliar with, and was kind of having a rough trip. I was hoping to cheer them up by being charming and witty.

What I said:
I pointed to a picture of a kali-like, skull-covered undead-looking female figure that was done in the style of H.R. Giger, and said (thinking myself witty), "Actually, that sort of reminds me of my mom a little."

My friend took a look at the picture, turned back to me and horror, and said something like "I don't know what's worse! That you would think that, or that you'd say that to someone!"

What I was thinking:
I did not actually mean what I said, I was just being flip. The picture was so dark and horrific, that the obvious thing to say seemed to be "Aww... it looks like mom!" I am such a geek, sometimes.

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The situation:
A friend had just gotten back the first copies of their first small-press publication that they had spent a year producing, and had painstakingly typeset and laid out from scratch using pre-computer cut and paste methods. It had been a huge undertaking, and finally, they had a finished product in their hands.

What I said:
It looks about how I expected it would.

What I was thinking:
I was thinking that with all the work they put into it, overcoming all sorts of difficulties, lack of funds, and lack of equipment, that they'd done an amazing job. Since the friend is a perfectionist, I could expect little more than that it would look really good. Needless to say, what they heard was "I expected it would look this crappy."

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While there may be some humor value in this stuff, for the most part, I feel so awful about the above incidents, that they will bother me in the middle of the night, even years later. If I dwell on them a little, it's to remind me to be very careful what I say, lest I really hurt someone's feelings when I don't want to.