You know you're in trouble when...

… You decide to co-star in a movie produced and directed by Kevin Costner.

…You break into Burt Gummer’s rec room.

…The nice young man you just invited into your house for coffee wears a black cape and has fangs.

…You’re a recurring character in Sunnydale, but you are never put in the opening credits.

Definitely the scariest thing in this entire thread.

Oh, I don’t know, I think hearing “Doug” would be just as frightening.

You’re the owner of a large electric corporation, and this young woman wearing trashy clothes keeps trespassing on your property.

You have a 16 year old daughter and you’ve just been named Drug Czar.

…you start to be known as The Person Formerly Known As [Your Former Name]."

(btw, WortMeWorry, nice one… didn’t want you to think that nobody got your Alan Dean Foster reference)
…you use any form of the phrase “I’m in a ______. What could go wrong?”. Bonus points if you stick in the word “possibly” before “go”.

…you’re making a Star Trek movie, and feel good about it, because the last one, which was even-numbered, was such a rousing success

…you are being treated at the ER of a large hospital in Chicago (likely by an extremely gorgeous person), and your condition seems slightly puzzling, but not particularly life threatening. Bonus points if you were brought in with a friend or family member whose condition seems much more serious than yours

…you messed with Jack Bauer’s family
(obscure ones)
…you see the message “you fall into a pit. More—” and then the floppy disk starts accessing, and accessing, and accessing…

…you’re one of The Forsaken, and it’s an odd-numbered book

…you’re any character at all in A Song of Ice and Fire

…the cheer choreographer you’ve just hired keeps ranting about “spirit fingers”

you hear jerry springer say: do you have any idea what your pregnant wife wants to tell you?

you’re on an airplane and you notice that your in-flight music selections consists of songs by Buddy Holly, Richie Valens, Otis Redding, Jim Croce, and Lynard Skynard.

You start up a perfectly innocent Pit thread and somebody throws out the word turdburglar.

. . . you decide your next step in World Conquest will be to invade Russia.

…it is high noon, your a sheriff, and someone who’s name is preceded with “Black” is coming to town.

…someone tells you, in a sword fight, that they’re not left handed.

…you wake up in Mexico.

…a one-armed man breaks into your house.

. . . you find yourself on a patrol boat going upriver with Martin Sheen.

. . . you are an outlaw, Indian, or bandido taking aim at the good guy from a rooftop, window, cliff, or other position from which you can fall spectacularly.

…your car has just been towed to a mechanic, who pops the hood and then yells to his partner, “Hey, Charlie, come look at this – I’ve never seen one this bad before!”*
*based on an actual incident involving Hometownboy

…you wake up and find yourself in a “Very Special” episode of Blossom.

…the management at your radio station is replaced and the new management promises not to make any changes.

…Columbo starts to walk away, then turns around and says, “Oh, just one more thing.”

It’s the 70s, you’re driving up and down the hilly part of San Francisco, and suddenly you hear bongos and a wahh-wahh guitar start playing.

You’re in a soap opera town, and you schedule your wedding/birthday party/big fundraiser/awards banquet for Friday.

You receive the script for your Law & Order episode, and you notice that you’re in the very first scene.

You’re Andy Sipowicz’s new partner.

And then you remember that it’s not just Law & Order, it’s Law & Order: Special Victims Unit.

… you ask your ship’s computer to open the pod bay doors, and hear the response “I’m sorry Dave, I can’t do that.”

… you find this really neat book of old incantations… in an old shack in a forest in the middle of nowhere… and you’re Bruce Campbell.

… you mispronounce the words “Klaatu Verata Nictu”

… you have to go somewhere for a minute. But you’ll be right back.

… your first assignment as a covert ops agent is in Raccoon City.

… you’re a big white horse belonging to a mythological character named Atreyu.

… you have a habit of saying “It never hurts to help!”. Tch’yeah right.

… you’re the scullery boy for a woman with dark hair and a white fringe, and this old man nicknamed “Wolf” keeps hanging around your farm…

… you’re a Zealot praetor in a temple, and you hear a dripping noise behind you.

… you’re in an abandoned space colony, and you hear a dripping noise behind you.

… you’ve just locked and barred a door to keep zombies out, and you hear - that’s right - a dripping noise behind you.

… your buddies tell you they have a CAN’T FAIL plan to win a high-stakes poker game with this British crime lord… you just need to come up with a few quid…

… you’re the last Gelfling.

… a fireman thinks you’re a circus midget.

You’re being interviewed by Stephen Colbert, and he’s agreeing with you.