A Canadian friend of mine (waving hello to Sim) was telling me of his various health issues, and I replied, “You’re a hot mess!” Every once in a while my Southern comes out of my mouth. I can’t help it. He had never heard the phrase before, and had to look it up. (Which charmed me to the tips of my toes.)
Out of pure curiosity, I decided to look it up, too. I was really surprised at the wide array of definitions, and none of them seemed to fit the true depth of feeling that this phrase evokes. So what follows is my rambling explanation. (I’d probably be able to be more concise if I weren’t such a hot mess myself.)
First of all, hot mess is not, repeat, not an insult. It’s like saying, “You’ve got so much going on, your life is such a mess, that I don’t know how you function, and yet you do, and I admire that like crazy.” It’s like calling someone a “real piece of work” but stripping all the negativity out of it.
If I consider you a hot mess, I appreciate you. I am also commiserating with you, and laughing with you. Make no mistake, I wouldn’t want to be you, and yet I think I’ve got a whole lot to learn from you about your ability to cope.
When this phrase came into being, it was more a physical comment. It usually referred to those lucky few who could be all scruffy and sloppy and yet still look great. It can still mean that, but over time it has also evolved into a more existential statement about being able to live a complicated, disorganized life with a whole lot of style.
So, mad respect for all those hot messes out there! Welcome aboard! It may be a bumpy ride, but it’s an adventure!
The View from a Drawbridge 
I love this phrase, I will definitely be using it in future!
Yay! I love enriching someone’s vocabulary. 🙂
You might want to use that term with caution–in some circles it means someone who is good-looking but crazy. I had one for a neighbor a couple years back, and the cops had the route to this building memorized….
That’s the craziest thing about this phase, it has such wide flexibility, even for slang. Thanks for the head’s up. (And it seems like there’s always ONE neighbor like that, doesn’t it?)
I would rather be a hot mess than a luke warm one…