"What is the biggest lie you have ever told?"
Dean froze. Not just because he couldn't tell this delicious girl, but also because he'd lied so much he hadn't the faintest idea what the biggest one was. But it didn't matter, because even if he did he wouldn't tell her. It was a game, Truth. He'd agreed to play because he'd thought she was smoking hot, but hadn't had the slightest thought that he'd actually tell the truth. Oh, the first few questions had been fine, and he'd learned she was single. Amazing. He was fairly sure he could get her easily. But then she'd asked that question. What a dreadful question. His entire life was a lie!
Maybe the biggest lie was that they were federal agents. Impersonating a federal agent could get you arrested if you're caught, but no-one knew that, and besides he doubted that was their biggest lie. I mean, honestly, he was hiding an entire WORLD filled with monsters from average ordinary girls such as this one... oh jeez, now she was staring at him because he wasn't answering.
Now, see, lying was usually not this big of a problem. Nah, if he was suspected as a federal agent he'd get the person to call Bobby. And it wasn't like this girl suspected him of anything (although she might now that he was totally silent after that question). It was just supposed to be a harmless question. One he couldn't possibly answer.
He could lie. Yes, lie about his biggest lie. Which in itself is a lie. Well of course a lie is a lie! He was just confusing himself now! But would that be his biggest lie? Was lieing about big lieing, his BIGGEST lieing? But then he hadn't actually lied to her yet, apart from telling her he was here on business with several large companies, which was technically the truth. Besides lying about lying was hardly anything at all, everyone did so. And now his head hurt with confusion.
"Uh." Was all he managed to say before downing his shot in one gulp and heading out of the bar, followed by the confused stares of many people, including the girl who's name he couldn't even remember. Well, at least he hadn't lied.
Okay, so Dean isn't much for internal monologue, but I figured that this sort of question to a person like him would cause a fair amount of thought. I hope it's enjoyable to read!