Confessions of a Bad Boy

“Who am I?” she says with mock-bitchiness to the beautiful girl in the tiny dress. “Who are you? I’m his wife of fifteen years. We have three children together. And he sold one of them to afford that suit he’s wearing.”


“What?” Sophia sputters, jerking her hand away from my arm.

“No. She’s not – I can explain,” I say, looking at Sophia pleadingly. Begging has never been a good look for me though. Before I can get anything else out, she shoots me a look of utter disgust before walking away far quicker than you’d expect in heels that high.

“Wait, Sophia! She’s not my wife, she’s just—” But she’s gone, and I turn back to Jessie. “Just my best friend’s annoying kid sister who hasn’t matured in the fifteen years I’ve known her.”

Jessie grins, snatches my beer out of my hands and swigs from it.

“What the hell are you doing here, Jessie? Besides ruining my night?” I snatch my beer back from her, and realize that it’s empty now.

“I told you, I’m looking for Kyle. I’ve got a feeling that he’s avoiding me.”

“He’s got the right idea. How did you even get in here dressed like that?”

I nod at her outfit. Jean cut-offs and a plaid shirt tied in a knot over a torn-up old band t-shirt, just short enough to tease the line of her hips, just soft enough to fall over the gaze-stealing teardrops of her breasts. Her dark, wavy hair makes her look like she just rolled out of bed, and her wrists are stacked with the kind of bangles and bracelets that you’d get in the kid’s section of a dollar store. It’s the kind of edgy-sexy, rocker chick look I normally can’t resist, but Jessie is, after all, like a sister to me. Which is why I drag my eyes away from her body and focus on the party still raging all around us.

“Oh, I’m sorry,” she says sarcastically, “I forgot to bring my Tiffany dress with the push-up bra. Am I not slutty enough for your Hollywood parties, Mr. Big-Shot Talent Agent?”

“No. It’s just that unless nineties grunge music is going to make a comeback in the next ten minutes, you look ridiculous. And for future reference, Tiffany sells jewelry – not clothes.”

“I look ridiculous? Look at you! That suit! Everything’s so…meticulous. Not a thread or a hair out of place. And so clean! It’s psychopathic. You look like a piece of furniture.”

I look up at the night sky, close my eyes, and take a deep breath.

“Well, thanks for scintillating conversation, Jessie. It’s always a pleasure. Take care of yourself.”

I start walking.

“Hey!” she calls out as she quickly catches up to me. “Where are you going?”

“First, I’m going to get myself another drink. Then I’m going to select one of these astonishingly beautiful women to come back to my apartment. And then I’m going to drink a Red Bull or three because lord knows I’m gonna be up all night long having fantastic—”

“Ew! Stop!” Jessie says, covering her ears dramatically for a second before grinning and punching my arm. “What about my brother? Where is he?”

“I already told you I don’t know,” I say, as I pretend not to inspect whether she’s damaged the sleeve of my suit. “I’ve been waiting for him for nearly an hour.”

“But I really need to talk to him. He said he’d be here.” The worry on her face is real, and I slow my pace and turn towards her.

“Look, it’s Kyle. He probably had a load of work dumped on him at the last minute. I’m sure he’s fine. Let me know when you find him. You still have my number, right?”

She nods. I move to go again. “Wait,” she says, tugging at my sleeve. I turn back to look at her. “I came all the way downtown by myself.”

Then she hits me with the full puppy dog eyes. I’ve seen that look a million times since we were kids. Usually it came when Kyle and I were going out and Jessie wanted to tag along. Sometimes it came when Jessie did something bad and needed me and Kyle to cover for her. Whatever it was, when Jessie made her eyes big and her lips pouty, as if she were about to cry, like she was the most vulnerable thing in the world – she always got her way.

“Let me guess. You’re low on cash, right?” I say, defeated.

She shrugs, looking a little embarrassed. “I spent what I had coming down here. I don’t get paid til next week.”

“Okay,” I sigh. “One drink. Then, if your brother still hasn’t shown up, I’ll get you a cab home. After which I’m definitely going to—”

“Go back to being a douchebag, I got it.” But her grin’s so wide now, I can’t even get mad that she’s teasing me again.

We enter the glass enclosure that houses a few couches and the bar. It’s nearly empty, everybody preferring to stand out on the roof and have their drinks delivered. I pull out a stool for her like a gentleman – and yeah, I can act like one when the situation requires it.

“Two beers please,” I call to the barman.

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