Love, Chicago

Episode One - Love, Chicago

Episode One - Love, Chicago

Sasha & Jack

Sasha Brennan opened the door to her loft, anxious to see the face of her older brother Trent. Instead, she was met with a wall of brown shopping bags that were piled three across and two high. 

“Where do you want these?”  The gruff voice panted.

Sasha looked at the hands gripping the bottom of the bags. The voice didn’t belong to her brother and Trent definitely didn’t have tattoos on any of his fingers. Or, at least, he didn’t have them the last time she saw him. And that was when…back in April?

Before Sasha could protest, the bags were coming at her. She stepped out of the way, avoiding the collision.

Her eyes narrowed at the back of the man’s head. His black hair was cropped and spiked on top. His dark blue t-shirt stretched over a wide, muscled back. His faded jeans looked like they should’ve been retired years ago and a chain-drive wallet hung off a frayed belt-loop into a well-worn back pocket.

Sasha reached up for the handles to the top row of bags and removed them, instantly feeling the weight of their contents. She locked eyes with the stranger for a moment and stammered. “You can set those on the table.” Deep-set, olive-colored eyes accented his ruggedly, handsome face.

The man hesitated, examining the young woman standing before him. 

Sasha was striking with her almost white-blonde hair that blended into a shocking blue color at the tips. The bob framed her face and sharply angled toward her chin. Her warm brown eyes were outlined in the same shocking blue shadow that matched her hair. Thanks to her wedge-heeled booties, Sasha was just a hair shorter than him. His eyes traveled to the skin peeking from the deep v-neck tunic she wore over black leggings.

Sasha led him to the mahogany table that separated the kitchen and dining area from the living room. She set the bags on the table. “Do you need me to sign for these?”

He grimaced and scratched at his short beard. “Sorry?”

“Oh, I should tip you, shouldn’t I?”  Sasha walked over to the coat tree by the front door, where her purse, along with other fall garments hung.

“Trent’s not here?”  He looked around the loft, his eyes grazing over the slate-colored sectional sofa and colorful throw pillows.

Sasha looked up from digging through her wallet. “Um, no?”

His expression grim, he sighed. “Trent didn’t tell you I was coming, did he?”

Sasha lowered her wallet.

The stranger pulled his cell from his pocket and tapped at the screen. Putting the phone to his ear, he glared into space.

“I’m sorry, who are you?”  Sasha tucked her wallet into her purse and set it on the black cushion of the dining room chair.

He glanced at her. “You’re kidding, right?”

Sasha blinked. Arrogant much?

He angled the phone toward his mouth. “Hey, yo, Trent, it’s me. I’m at your sister’s. Call me when you get this.”  He tapped his phone again with his thumb.

“Trent didn’t tell me he invited anyone.”  Sasha cocked her head. “You’re welcome to stay, I’m just afraid I don’t know who you are.”

He scoffed and shook his head, staring at his phone as he typed.

Sasha put her hands on her hips and frowned. She was just short of tapping her foot if he kept ignoring her.

He closed the application on his phone and slid it in his front pocket. His smile was strained. “You don’t watch wrestling, I take it. Even though your brother is a wrestler.”

Sasha crossed her arms. “I don’t really follow it, no. And yes, I’m aware what my brother does. Are you on his team or something?”

“His…his team.”  He looked up to the ceiling and bit his lower lip. “I’m not…unless we tag team, but no, there are no teams, as you say, in wrestling.”

Sasha rolled her eyes and walked over to the counter next to the sink. She picked up the bottle of wine she was planning on opening for dinner, deciding now was as good a time as any. “But you do have a name?”


Sasha struggled with the bottle’s aluminum foil top. Her hands pausing, she looked up at him. “What did you say?”

He crossed through the kitchen and took the bottle out of her hands, expertly removing the foil in one fluid movement. He picked up the corkscrew from the counter and began to push the tip into the cork. “Crusher. Crusher Webb. That’s my name.”

Sasha considered what he said for a moment. “That’s a nickname.”

The wine bottle cork lightly popped and he reached for the glass on the counter. A mischievous smile spread across his face as he poured.

Sasha put her hand on her hip. “What’s your real name?”

“I told you. Crusher.”  He held out the glass, offering it to her.

Sasha reached for the glass but Crusher pulled back before her fingers could touch it and took a long drink. She let out an exasperated sigh. “I refuse to believe that’s your real name. I’m not calling you Crusher. I don’t call Trent by his silly little name.”

His glare produced a lump in Sasha’s throat. He set the glass and the bottle on the counter. “Our names are not silly. They’re tradition and they’re who we are.”

Sasha sighed. “To me, Trent is Trent, not Babyface Brennan.”

The corner of his mouth turned up as he slowly nodded. “He’s totally Babyface. He’s got those young features.”  He reached out and cupped her chin briefly. “Same as yours, Brown Eyes.”

Sasha flinched under the light touch of his fingers. She blinked and turned away. “Is that my nickname now?  Because I don’t need one.”  She went to the sink as if she had a job to do there.

Sasha felt him behind her. She could see him in her peripheral vision over her right shoulder and a chill ran through her. I don’t know this guy, he could have said he knows Trent but he could be anyone, maybe some sort of serial killer. Would a serial killer bring you dinner first? Sasha glanced into the other side of the sink, searching for the large kitchen knife.

“Jack,” he murmured in her ear.

Sasha felt her heart stop for a moment. His breath warmed her neck making her skin tingle. She turned her head slightly. “What?”

Jack rotated next to her and leaned his lower back against the edge of the counter as he crossed his arms. “Jack Webb. My real name is Jack. But not many people call me that. Usually only…people I care about.”

Sasha’s eyes slowly ran up his muscular inked arm, settling on his face. He stared at the floor. She defiantly reached across his chest for the wine glass next to him. Jack’s eyes darted up to hers. 

Sasha raised the glass to her lips and paused. “Well, Jack, it’s nice to meet you.”

Jack’s lips curved into a small smile as he watched her finish off the wine. 

“Help yourself to a glass in the cabinet behind you.”

Jack picked up the wine bottle.

Sasha regarded his tattoos as he poured the red liquid into her glass. “Am I going to find ink on my brother when he arrives?”  She took the glass to the dining table, setting it down on the rust-colored table runner.

“Not any that you can see, based on where they’re at.”  He retrieved a glass from the cabinet.

Sasha pulled a bag of russet potatoes out of one of the shopping bags and held it for a moment, contemplating what he said.

Jack chuckled at her expression and picked up the empty bag to fold it. “I’m just teasing you. He doesn’t have any.”  He paused. “Yet.”

Sasha shook her head. “Well, just make sure he doesn’t get some girl’s name. Nothing jinxes a relationship more than getting someone’s name on your skin.”

“Are you speaking from experience?”  Jack raised an eyebrow at her.

“No, but you know how it is. Ink is forever and sometimes love is not.” She shrugged, reaching into another bag.

Jack blinked. “Wow, that’s such a cynical way to look at life. Why so jaded?”  

“Not jaded. Just realistic.” Sasha pulled a container out of the final bag. “What’s this?”  She asked, looking at the unmarked glass jar.

Jack reached out for the container, setting his wine glass down. “That’s a special after-dinner drink.”  Jack took the container on refrigerator and returned to the table. He picked up his wine glass and swirled the liquid. “Have faith. It’ll be great.”

“If Trent ever gets here.”  Sasha looked at her watch.


Devyn & Todd

Red brake lights lined Lake Shore Drive from Belmont to the Hancock building and Devyn Deveroux swore as her phone started to ring.

She pushed the button on her bluetooth earpiece; already knowing it was her boss.

“Traffic sucks.” She didn’t bother with niceties; it was Todd, after all. She pushed her long brown bangs to the side, a habit she’d acquired since she’d gotten her hair done a month ago. The stylist insisted they chop off everything but Dev’s bangs, telling her it was flattering for her oval face. Dev found it occasionally annoying, but she didn’t miss the time it used to take to dry her hair in the morning.

“Are you going to make deadline or what?” Todd Whitmore sounded rushed.

Dev peered across the dashboard of her Mini Cooper, assessing her options. “I think I'm going to have to pull over and email you the shots. Give me about twenty minutes.” She glanced up at the rearview mirror and turned in her seat as she clicked on her signal. 

“Okay.” Todd paused and lowered his voice. “Will I see you later?”

The corner of Dev’s mouth turned up. “We’ll see about that,” she joked. She knew in a few hours she’d be in his bed but Dev liked to tease him.

The secrecy of their relationship gave her a little thrill. Todd had insisted they keep their affair under wraps and Dev agreed, not wanting anyone to think she had her job because she was screwing the boss. Although on nights like this, she wondered why she even cared. This job wasn’t exactly the dream career she had hoped for.

Dev worked for Chicago’s top online gossip magazine - Windy City Scandalous - where Todd Whitmore was editor-in-chief. A professional bachelor, Todd was significantly older than Dev, almost two decades, but that didn’t bother her. She was grateful for those years of experience. She could learn from Todd versus struggling blindly like most of her colleagues, even if it wasn’t the most respected job in the field of photography.

Her business card said “Staff Photographer” but the nickname for what she did was “Paparazzi” and Dev knew that was the more realistic title. She chased down Chicago athletes, entertainers, politicians and anyone remotely famous visiting her windy city, catching them in normal life routines for the online magazine. WCS had national recognition thanks to other popular celebrity news sites, such as TMZ. People were ravenous for gossip, it was a reality Dev couldn’t deny and it was making her really good money.

Knowing the knee-jerk reaction most of her targets had toward the paparazzi, Dev tried to be as polite as she could when she was snapping photos. If the Mayor were losing a scrimmage to one of the young Chicago Bulls basketball players, Dev would shout out, “maybe next time, Mayor.” If she was posted outside a building and some top female singer was leaving rehab, Dev would be sure to wish her “best of luck.”

Perhaps it was her looks that helped her get away with it. Dev was petite with large expressive hazel eyes that always seemed to smile. Her fashion choices were also different from most of the paparazzi she knew - albeit most of them were male. Even if Dev wore black to blend into the background, she was wearing stylist boots and designer clothes doing it.

Dev irritated the other drivers on LSD as she forced her way through their lanes to get to the right shoulder. The sun was just setting and the wind off the lake was picking up. Her Michael Kors scarf fluttered around her neck as she hopped out of the car to retrieve her laptop and camera in the trunk, quickly returning to the front seat of her car. 

The camera’s memory card held pictures from the set of a movie being filmed at Wrigley Field and Dev had captured the two lead stars, making out, outside one of the trailers. The two stars were not being filmed for a scene at the time and both are married to other people. The thought of what it would do to the individuals involved crossed Dev’s mind but getting the scoop, and proving herself to Todd, trumped the wake of coverage the stars would get going forward. 

Dev reminded herself, self-righteously, the two actors were cheating. She had a serious problem with that particular side effect of celebrity. Dev couldn’t understand the idea of marrying one person then screwing around with another. Her heart only had room for one person. Right now, Todd was probably that one person, but she hadn’t settled on that decision just yet. She only knew there was a strong attraction and a job connected to it. Yes, Todd was fun in bed, and sure, things could get awkward if people found out. Of course, she wasn’t exactly in an admirable position being paparazzi. If she was going to accept her lot in life - big if, she reminded herself - then why not go all out and accept the consequences? And if she really cared what people thought, she’d have quit the job - and Todd - a long time ago.

Dev sent the pictures over to Todd’s WCS email and shut her laptop. Soon, Todd would be posting them along with commentary from one of the staff writers. She glanced over to the inner drive where two people were huddled together, walking their dog. She slipped the memory card back into the camera and found the couple in her viewfinder, zooming in. They looked to be in their forties and they exchanged smiles as they slowly walked. When the dog, a standard poodle, stopped to sniff the guard rail, the couple took the opportunity to steal a kiss.  Dev unconsciously snapped a picture and pulled back to look at the screen.  Their lips still in the form of smiles as they connected, the man’s hand around the woman’s, the same hand holding the leash.  The dog had turned to look up at them just as they kissed.

Dev smiled at the picture. At least there’s hope for some people, she thought as she stuffed the camera back into her bag.

Dev pulled back onto the road slowly and her phone rang again.

It was Todd. “Nice shots, Dev. Why don’t you just meet me at my place? I’m going to upload these and get out of here.”

He must’ve been in his office because he wasn’t speaking in his usual hushed tone.

“Maybe we can go for a walk tonight?” Dev asked, still thinking about the couple.

“A walk?” Todd scoffed. “Honey, you know we can’t. What if someone sees us?”

Dev shrugged, despite no one being able to see her expression of hope for the relationship. “Would it be so bad?”

Todd laughed, as if she were joking. “See you soon, babe. Nice work as always.”

Dev sighed. Maybe it was time to start making some changes in her life.


Ashleigh & Ryder

Ashleigh Taylor wished the cabbie would just drive a little faster. She would even pay for the speeding ticket if he would just get her to the House of Blues sooner rather than later. 

She was running late and it was all Izzie’s fault. 

Ashleigh had just released her third Young Adult novel and while her agent, Isabel Duran, aka Izzie, knew it was going to be another hit, Ashleigh was still expected to run the circuit of readings, signings and lectures. Ashleigh specifically told Izzie to stay away from this weekend. Of course, it was only Thursday, technically not the weekend, but Izzie knew what this weekend meant to Ash.

It had been almost a decade since Ashleigh had seen her old friend, Ryder Jones. It felt like yesterday they were kids - Ryder playing guitar in his garage, while Ashleigh journaled from the old couch Ryder had pushed up against the wall for the occasional weekend audience of classmates. Growing up across the street from each other since birth, their parents were best friends. Their moms were always planning the yearly block party, their dads golfed every other Sunday, and Ash and Ryder assumed a similar relationship. They were inseparable.

After high school ended, they spent one last summer hanging out before Ryder left for California to find fame with his band, and Ashleigh was off to college. Over the years since, they kept in constant contact with emails and calls but his visits home got to be fewer and fewer and admittedly, the last time they saw each other in person, it didn’t go so well.

Ashleigh shifted in the back of the cab, pushing the memory out of her mind and checked her watch. She brushed the lint off her dark denim jeans and adjusted the neckline of her revealing cowl neck top. The lavender fabric peeked out from under her black, leather jacket. Thanks to her stylist, Sasha Brennan, Ash learned how to find great options for her tall frame without looking like an amazon. With a few designer items in her wardrobe, she came off as sophisticated without being too pretentious. She fluffed out her long, auburn hair and it curled loosely around her shoulders.

The cab pulled into the drop-off area in front of the House of Blues and Ashleigh felt her heart start to race. She fumbled with her money and realized, too late, she’d tipped the driver way too well. She shrugged it off as her boots hit the pavement and she headed inside.

Drink first, she thought, taking the short stairway to the restaurant. She needed to calm her nerves. She had just spent the last three hours reading excerpts and signing copies of her books in front of a huge crowd of her enthusiastic, young fans. That, alone, would have given anyone an anxiety attack. But it was seeing this one person, “her Ryder”, after years of missed opportunities, that made her teeth chatter and her knees quake.

The first shot went down quick, and hot, and Ashleigh nursed the second shot for a few minutes before paying her tab and heading into the concert hall.

The opening band was already playing - Ashleigh didn’t recognize them but the small crowd that congregated at the stage sure loved them. She found a spot at the bar on the side of the stage and ordered a glass of wine. In his voicemail, Ryder promised they'd get together after the show, after the meet and greet with the fans for which she’d been given a VIP pass. That was the extent of the plans. Whether that meant dinner, drinks, hanging out at her place, his hotel, she was clueless. She reminded herself it could also mean a quick hello and that would be it. But she truly hoped it would be more than that.

Only Izzie knew Ashleigh’s true feelings for Ryder. Feelings that went all the way back to their last two years of high school. Izzie had a way of supplying Ash with too many martinis and getting her to open up about her real feelings for Ryder. On more than one occasion, Iz got her to admit that every male character Ash wrote about included a little bit of Ryder in them. Sober, Ashleigh scoffed at the idea, claiming hours of research went into creating her characters and none of which were rock stars.

But an hour later, when The Ryder Jones Orchestra, took the stage, Ashleigh felt like a giddy school girl, back in the garage across the street from her house, and she wondered if maybe a little bit of those old feelings had made their way into her novels.

By now, the main floor and balcony were jam-packed with cheering fans, all significantly buzzed from booze and ready for a show. As soon as they saw Ryder, their cheers got louder and Ashleigh had to look through dozens of raised arms to catch a glimpse. When she saw him, a smile spread across her face.

Ashleigh’s stomach did a little flip flop as Ryder walked across the stage. His tall, thin frame was covered in black from his tight jeans and motorcycle boots to his sleeveless cotton shirt. Even his signature Fender guitar, slung around his back, was shiny and black. His dark blonde hair was slicked back and around his right wrist he wore several leather strap bracelets, similar to ones he used to wear when they were teenagers. Ryder waved at the crowd and scanned the front row of fans. He reached out to give high fives and fist bumps then turned toward his band and raised his arms as they ripped into a song.

The crowd started to bounce on their feet and cheer even louder. Ryder turned into the microphone and started to sing. Known for his rockabilly style, Ryder had always loved the music from the fifties. His albums brought back huge public interest in the genre and his concerts over the last five years had been complete sellouts. Tonight was the last show of the current tour and by the look on his face for the full two hours of the concert; Ryder was loving every minute of it.

Ashleigh watched and memories of a decade ago found their way into her thoughts.

Specifically, the summer before they went their separate ways.

Kelly DuffComment