Confessions of a Bad Boy

I nod, but I’m having a hard time getting as riled up as my friend is about Jessie’s job. Maybe because I know the entertainment industry all too well. “So she works hard.”


Kyle slams his beer down and shakes his head. “For what? So that she can say she’s ‘chasing her dream’ over and over again? Shit. The hardest working street cleaner doesn’t become CEO of the company – any fool knows that. She needs to get her head out of her ass and start acting like an adult.”

“So what would you have her do? Give up on her dreams and…what?”

“Get a real fucking job!” Kyle says, directing his frustration at me like I’m standing in for Jessie. “Do something that pays well and doesn’t ask you to play butler to a bunch of has-beens on a TV show made for people who lose their remotes and can’t change the channel.”

“It’s not as easy as—”

“You know where this is heading, right?” Kyle interrupts, too full of steam to listen now. “’Cause I can tell you. I’m the one who’s going to end up having to fix all this. If Jessie doesn’t grow up fast she’s going to find herself too old to change, with no other prospects, and nobody else to turn to. Then it’ll be time for the big brother to step in, like I always do. I don’t want her to give up on what she loves, but it’s leading her down the wrong path. And I know I’m gonna be the one who ends up paying her rent and picking up the pieces.”

I pause before speaking, waiting for the dust to settle.

“It’s shitty, I know. But come on, dude. She could say the same about you. What is this, the third time we’ve had a drink this month? And you’re going to leave early again, to go on yet another business trip. You even told me you work through your lunch breaks, and where has it all led so far? You guys are more similar than you think.”

“The difference is,” Kyle growls, as soon as I finish, “that I’ve got something to show for my hard work. Big fucking difference. Me, I’ll probably end the year on six figures, and I’m this close to making partner. If I do well in London, I am going to be one step closer to being a made man. She doesn’t even get benefits, Nate. They could fire her tomorrow and she’d have fuck all to show for it. Nothing! She’s wasting her fucking life.”

“Kyle, she’s—”

“You don’t get it!” he interrupts, unable to stop himself now he’s built up momentum. “You’ve had your lucky breaks and now you don’t have to worry about any of this shit. But she’s never gonna get lucky like that. I’m not the bad guy here. I’m just a realist.”

Kyle glowers at me, his face red, his eyes narrowed. I stare back.

“I’ve paid for my luck, Kyle.”

Kyle hangs his head, breathing out his hot anger.

“Shit. I know you have, Nate. I’m sorry.”

“I don’t expect most people to see that, Kyle, but you’ve known me long enough to know better.”

“That was out of line, I get it. I’m just pissed. I want better for her, and I worry.”

I look over at the barman and gesture for him to bring a few whiskeys over.

“Look, you’re probably right, Kyle. Jessie is way too good to still be doing what she’s doing. She’s probably stuck in a rut. But you can’t fight her over these things. She’s still your little sister, but she’s also a grown woman now who needs to figure shit out for herself. The best you can do is be a big brother, look out for her, give her some support. Not fight with her over it.”

Kyle looks at his drink for a long time, then shakes his head.

“You’re right.”

“I mean, when did fighting ever work on her anyway? She loves one as much as you do. Maybe more.”

“Would you talk to her?”

I roll my head to the side in a gesture that says ‘not good idea.’

“I dunno…she’d probably figure out that you asked me to.”

“But she’d still listen. You’ve always been the voice of reason between us. Come on, dude.”

“Okay,” I sigh. “If it’s really as bad with her as you say, then I’m sure all she needs is a fresh perspective.”

“Right,” Kyle says, nodding with enthusiasm at the idea. “Also, she’s got a new boyfriend.” He shakes his head in disgust and slams down his whiskey, waving the barman over and ordering us another round.

“What’s he like?” I ask, although I already know Kyle hates him. He always hates Jessie’s boyfriends. No guy is good enough for his sister, as far as he’s concerned.

“I don’t know,” Kyle shrugs. “I think she’s hiding him from me.”

“That’s smart of her,” I grin. “Whoever he is, I’m sure he won’t meet with your approval.”

He looks at me sharply. “Actually, I was gonna ask. Do you think you could—”

“No. No I won’t find out everything I can about him and report back to you. Even if he’s an asshole, Jessie is big enough and tough enough to figure it out herself. Gotta let her make her own mistakes, dude. Same as you did.”

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