15| Dean the Flirting Coach

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As soon as Charlie got to level 4 of the building, Sam hit the button to start the looped footage on the cameras, which meant we lost visual, but still had contact via my phone which currently was in Dean's hand. I had sat down near Maddie, resting for a minute since Zep had finally managed to fall asleep.

"I'm in," Charlie's voice carried through my speaker. "I've always wanted to say that."

"You're on the clock," Dean informed her. "Move."

It fell silent for a few minutes and then Charlie's voice came through again, but it sounded like she was whispering this time.

"Hey, there's a bigass guard up here, blocking the door. What do I do?"

"Just wait him out," Dean told her.

"He's not going anywhere."

"Okay, you work there every day. Do you know the guy?"

"I guess. I mean, I've seen him. I've never talked to him."

"Okay, when you've seen him, does he look at you, or does he just kind of slide his eyes by?"

"Um... eye contact? I don't know. He always kind of smiles a bit. I don't really-"

"Good," Dean cut her off. "What you're gonna do is you're gonna walk up to him, and you're gonna flirt your way past."

"I can't. He's not my type."

"You're gonna have to play through that."

"As in he's not a girl," Charlie hissed, confirming my theory from earlier.

"Oh, oh," Dean said, looking at me. "Pretend he has boobs."

"Worse."

"Well, I don't know. Um, do you have any tattoos? Give him a little sneak peek there. All tattoos are sexy."

I rolled my eyes as Charlie answered.

"Mine is Princess Leia in a slave bikini straddling a 20-sided die."

Dean didn't reply, looking over at Sam this time.

"I was drunk. It was Comic-Con," Charlie defended.

"We've all been there," Dean muttered. "Okay, I'm going to walk you through this. Start with a smile. Relax, Charlie. You just got home, and Scarlett Johansson's waiting for you."

There was a content hum from Charlie's side of the phone.

"Can I help you, miss?"

"Hey... Bill. Charlie from I.T."

"Oh. Burning the midnight oil, huh?"

"Just like you- I mean, when you're not at the gym. What, do you work out with all your free time?" Dean supplied and Charlie repeated.

"I try to get to the gym at least three times a week," Bill's voice carried through the speaker.

"It shows," Dean said, glaring at Sam and I. "You look amazing."

"It shows. You look amazing," Charlie echoed.

"This never happened," Dean hissed at us, then spoke into the phone. "Do you ever do anything else in your free time, like take a girl out for a drink?"

As Charlie repeated the question Sam started to laugh and I snorted a little.

"Stop laughing, Sammy," Dean told him.

"Stop laughing, Sammy," Charlie repeated, then realized what she just said. "Um... y-you know that bar, Stop Laughing, Sammy?"

Sam put a hand over his mouth to stifle his laughter as I laughed softly myself.

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