Taking a Chance on Love

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Chapter 1


Here she was, feeling humiliated because her date had apparently stood her up and who shows up to witness it?

The bane of her existence. Her big brother’s stupid best friend. Henry.

Just great.

Jess knew she wasn’t going to hear the end of this for a month. And what made the situation even better? Henry had a bombshell of a date hanging on his arm.

Jessica’s gaze travelled over the ditz’s outfit, from her perfectly coiffed bleach blonde hair, to her pornstar makeup, to her hot pink dress that was straining to contain her curves, and down to her four-inch, hot pink, fuck-me shoes.

Ugh. What a tramp.

She should just go do Dallas already, like Debbie did.

Okay, Jess knew that was catty of her, but she’d been stood up. She was in a mood.

Jessica’s gaze flicked back to Henry and she realized he hadn’t noticed her yet. She started chanting at him in her head.

Don’t see me. Don’t see me. Don’t. See. Me.


He saw her annnd... started walking towards her table.


And damn him. He looked good tonight, dressed in dark slacks, and a light blue, button down shirt. She hated to admit it, but Henry always looked good. As a kid, he’d been a bit on the scrawny side, but he’d grown up nice. With his dark hair and eyes, his chiseled jaw - which usually sported scruff - and his trim physique, he was her type.

If he wasn’t such an asshat to her all the time, Jessica might have had a harder time ignoring any attraction she felt for him... but... he was an asshat to her more often than not, so that made ignoring easy.

Jessica put on what hopefully resembled a smile, while cursing in her head.

Stupid online dating site. They claimed they helped bring together all these couples. Pfft. She’d been on the site for months and gotten nowhere.

The guy she was supposed to meet tonight... Scott... was one of the few guys she’d met that hadn’t been trolling for a hook up. He’d actually seemed like a viable prospect... and he’d stood her up.

If that wasn’t bad enough, Henry was here to witness her date fail.

“Hey, Maybel.” Henry smiled down on her, coming to a stop at her table, his date by his side.

Jessica gave him a withering look. He knew she hated her middle name. She’d only told him not to call her Maybel a million times.

He smiled, turned his gaze to the blonde at his side and introduced her.

“Jessica, this is Trixie. Trixie this is Jessica.”

Trixie? Really?

Although, maybe the name suited her... she probably performed a lot of ‘tricks’ in bed.

Wow. She really was being catty.

Jessica bestowed a smile on Trixie and mumbled a ‘nice to meet you.’ And Trixie did the same.

Good. They were both on the same page. Neither of them were interested in being friends.

“So what are you doing here Maybel?” Henry asked.

“I thought you said her name was Jessica, why do you keep calling her Maybel?” Trixie asked, her over-shaped brows furrowing.

“Maybel is my middle name.” Jessica explained.

“It bugs the hell out of her when I call her that.” Henry added.

And he just loved to irritate her, didn’t he, Jessica thought, resisting the urge to roll her eyes.

She got that urge a lot when Henry was around.

Irritating her hadn’t always been on Henry’s list of favourite things to do... cue wistful sigh. The good old times.

The two of them, and her older brother, Josh, had had a lot of fun together back when they’d been kids.

Jessica had been a bit of a tomboy growing up and had wanted to be a part of the shenanigans Josh and his best friend, Henry, got up to. They hadn’t wanted a girl tagging along with them at first, but she’d proved herself by taking all their dares, talking sports as well as playing them, and having as much fun doing gross stuff as they did.

For three years they’d been like the three musketeers, then Henry had turned their trio into an all male duo. Jessica had been twelve, and Henry and Josh fourteen, when all of a sudden Henry had had a stick up his ass when it came to her. He’d started teasing her and making fun of her, upping his game to more and more annoying levels until she’d had enough and stopped hanging out with them.

The jerk.

“What are you doing here? You by yourself?” Henry asked, interrupting her thoughts.

“Yes, I am.” she admitted. “I was supposed to meet someone at 6, but it’s now, ” she checked her watch, raising her eyebrows when she saw the time, “6:40 and he hasn’t showed.”

“Blind date?” Henry asked.

Jessica nodded reluctantly, anticipating the dig she knew Henry was about to make.

“Are you worried he came in, took one look at you and left?” Henry asked, a teasing smirk on his stupid face.

Jessica sighed mentally. Henry was so predictable.

Trixie swatted him on the arm. “That’s not nice muffin.”


“Yeah, that’s not very nice... muffin.” Jessica repeated with inner glee, smiling in satisfaction when Henry shot her a little look. Apparently he didn’t like Trixie’s nickname for him. Or he just didn’t like Jessica using Trixie’s nickname for him.

Excellent. He’d be hearing it a lot more from her in the future then.

“Oh, she knows I was just kidding.” Henry reassured Trixie.

“Of course I do, muffin.” Jessica replied before gathering her purse and jacket.

Henry was always ‘just kidding’ with her.

She pushed back from her table and stood up. The exit sign had her name written all over it. She’d waited long enough for Scott.

“I’m not going to wait around any longer. ” she said. “You two can have this table.”

Rigatoni’s was a popular Italian restaurant and it being a Friday night, the place was full up.

“Thanks.” Trixie said and left Henry’s side to flounce into the chair Jessica had vacated.

“Thanks.” Henry echoed, turning to face Jessica as she maneuvered around him in the tight aisle between tables.

“No problem.” Jessica said. “I obviously don’t need it, what with having scared my date away.” she might as well make his crack for him.

Henry didn’t comment. He just gazed at her for so long that she started to feel uncomfortable. Was her little black dress too wrinkly? Her hair too flat? Her makeup smeared?

“What?” she asked, raising a hand to her cheek. “Do I have something on my face?”

“No.” Henry reassured her. “Sorry your night was a bust.” he added, sounding sincere.

This small show of compassion was a surprise coming from Henry. Jess didn’t know how to digest it.

“Uh... thanks?” she replied, the word coming out more as a question.

“It was his loss. You look...” Henry scoped her out from head to toe, taking in her subtle makeup, her LBD and her black strappy heels, “... amazing.”

Okay. What was happening?

Jessica was not prepared for Henry’s lapse in immaturity. Encounters with him usually included him teasing her, him making her the butt of lame jokes, and him generally irritating the hell out of her. They never included compliments. His being nice to her, was making her feel off balance.

“Uh... thanks?” she repeated, dumbly.

Henry laughed softly at her expression and Jessica thought he looked kinda sad for a moment, but she couldn’t be sure because the look was gone so fast.

“G’night.” Henry said.

“G’night.” Jessica replied and moved towards the exit while Henry turned away and took a seat across from his date.

Disappointment over getting stood up filled her as she made her way out of the restaurant and across the parking lot to her car. The scent of garlic hung in the air even outside the restaurant, reminding her of the pasta and garlic bread she’d been looking forward to having tonight.

Oh, well.

She’d saved herself some calories.

Two quick beeps sounded as she unlocked her doors and let herself into her Hyundai. Starting the engine, her gaze moved back to the front window of Rigatoni’s. She could just see Henry and Trixie perusing their menus through the tinted glass.

For a moment, watching Henry and his date, Jess felt the loss of his friendship again. She’d been so sad, so hurt, when he’d changed on her all those years ago. She’d really missed her friend.

But then, he’d annoyed her beyond the point of missing him anymore.

The jerk.

Recalling how he had started antagonizing her, Jessica firmed her lips, pulled her gaze away from him. Shoving her old hurt back into the depths of her memory bank, she backed out of her parking spot and headed home to a frozen dinner and a pint of Ben and Jerry’s.

Maybe she wouldn’t be saving that many calories tonight after all.

Oh, well. She needed some Chunky Monkey after getting stood up.


Whoever the guy was that had stood up Jessica was a moron. An absolute dipshit.

When Henry had seen Jess at that table, with her brown hair down and loose around her face, her shoulders bare except for two thin straps holding up her dress, he’d almost forgotten about the blonde at his side.

But, he’d given himself a mental head shake and put on his game face - the one reserved for encounters with the little sister of his best friend, Josh - the one he’d had to hide behind ever since that day when he’d looked at her and not seen a buddy anymore.

That day he’d felt an attraction to Jess for the first time, had shoved him off balance. He’d been fourteen, and she’d been twelve. He’d been full of budding hormones, and she’d yet to enter the hormonal upheaval that was the joy of adolescence. He’d felt so awkward with his new awareness of her. Add in the fact that she was Josh’s little sister, and things were even more awkward.

So... he’d kept his attraction to her to himself, and pushed her away.

Henry pulled himself from his thoughts, refocused on Trixie, nodding along as she talked about stuff he didn’t give a crap about.

Why had he gone out with this girl?

Oh, right. Because he couldn’t have the woman he really wanted.

He tried to give Trixie the proper attention, but her running commentary on celebrities was boring. His heart just wasn’t into putting much effort into this date. Seeing Jessica, unexpectedly like that, had thrown him off his stride.

It was a relief when they finished their meals and got their bill. He drove her home, where he walked her to her door quickly and efficiently.

“Do you want to come in for a cup of coffee?” Trixie asked coyly, leaning back against her front door, a hand delicately running across the top of her dress, trying to draw his gaze down to her cleavage.

By ‘cup of coffee’ she obviously didn’t mean cup of coffee.

“Not tonight.” Henry said apologetically. “I’ve got an early morning tomorrow. I should get going.”

He didn’t really have an early morning the next day. Well, no earlier than usual. He and Josh had their own handy-man business and made their own hours. They usually started at eight, and called it a day around six.

Trixie pouted at his words.

“You sure?” she asked, pushing off the door and stepping into him, running a hand slowly from his chest down to his stomach. “I can make decaf.”

Translation: We can have a quickie.

“Thanks, but I can’t.” Henry said, as politely as he could, not even remotely tempted.

“I should go.” he repeated, clasping her hand and gently lowering it to her side. “G’night.” he released that hand.

“G’night.” Trixie returned, voice heavy with disappointment.

Henry turned and walked back to his truck. He got in and started the engine, waited for Trixie to disappear inside her duplex before reversing out of her driveway and heading home. By the time he reached his apartment building and turned into its underground parking, he’d decided he was going to take a break from dating.

For a while now, he’d been hoping he’d meet someone and that someone would help him get over Jessica, but that hadn’t happened so far. At this point, he didn’t think that was ever going to happen.

No matter how many dates he went on, no matter how great the woman was that he was with... after all these years, his heart was still set on Jessica Marlin. The damn thing would not be distracted, would not give anyone else a chance.

Frustrated, Henry got out of his truck, rode the elevator up to his floor. After letting himself into his apartment, he relocked things and went to bed, getting into the jogging pants he wore as pj’s and getting between the sheets.

As he lay in the dark, he asked himself questions he’d asked himself countless times over the years... what if he asked Jess out on a date... what if things went well? What if they fell in love? Got married? Lived happily ever after?

Those questions were quickly put down, as they always were. They were unable to stand up to the voice in his head that pointed out most couples didn’t live happily ever after.

Henry really hated that voice, but... it was right. So, he heeded it, as he had for the last thirteen years and he put his wishful thinking away, and shut his eyes and went to sleep.


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