Choking on carrots

Why, oh why, is my life a constant stream of "Why did I saaaaaaayyyy that??!!"

Today's exhibit A: At my second day at a new internship, I am leaving for the night and checking in with my boss. I tell her that I'm getting my bearings, and that I've done a, b, and c. She tells me that she'll be gone on Thursday and Friday, but she'll try to think of some things for me to do (being new, it is a struggle for me to find things to do). I clumsily reply, "Well, if I can't find something to do, I can always leave early."

That's probably in a manual somewhere entitled: "What not to say on your first day of work".

Whenever these things happen, there's always that justifying sentiment behind it--in this case, what I MEANT was that I didn't want to cost the place money by logging in hours when I can't find things to do, and really I can't be expected to think of things on my own yet. Usually I am quite resourceful but this isn't a restaurant, it's an office. That I don't know. You can't just start running salads out to tables.

But while I can walk home hoping that my boss understood the complex implications of my stupid statement, she probably didn't. And she (hopefully) probably forgot all about it two seconds later. But it will continue to torment me for several hours. When I say something I think may have hurt or offended someone, I often feel this torment is my punishment. I would bet that most times, the agony I experience outweighs the hurt I have inflicted.

This is not, however, the rule. There is one instance I remember as being the hugest, meanest blooper of all time; I was out with a guy that I didn't really want to see anymore, mostly because I had come to realize that his anxiety level was superior to my own--already high enough itself--and in the long run, I was going to need someone calm, to reassure me, not wind me up tighter. As I tried to explain that I wanted to be "just friends" (yes, yes, I know), he broke in with this accusation:
"Yeah, yeah, I get it. You think I'm funny, and we laugh together, but at the end of the day you're just not physically attracted to me. Fine."
Well, I didn't think this was fair, because no, I wasn't really attracted to him, but it was more about the anxiety than his looks. He told me he would never ever sing karaoke, he was that scared! I may be anxious but I can make a fool of myself. And have a hard time respecting someone who can't.
I fumbled at trying to rebuff this exaggerated view of his; I began thinking of how my little sister always thinks I date weird-looking guys, that apparently only I would think are cute. Trying to put this into words, and flustered, I floundered, and came up with this gem:
"You know, I've dated guys uglier than you."

Just take a moment and let that awkwardness sink in. That's what we did. A flurry of apologies and explanations ensued--hey, at least this time I did get the chance to explain what I really meant.

But if only I had slightly re-phrased the sentence:
"You know, I've dated guys LESS ATTRACTIVE than you."

And therein lies the rub. Oh, the agony.

Turns out he was kind of a creep, so the life-long complex I gave him was at least partially deserved.

Or not...you're probably wondering how I can sleep at night.

What's the worst thing you've (accidentally) said to someone?