Taking a Chance on Love

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Chapter 8

A smile stuck on her face, Jess exited Henry’s apartment building and crossed the sun-baked parking lot to her car.

She got into her Hyundai, and got the a/c blasting through the oven box it had become, then texted Laura, eager to share her news.

I talked to Henry. she thumbed in quickly. He wants to give us a shot!

She waited a moment, expecting an instant reply to that exciting news, but no dots popped up indicating Laura was messaging her back.

It was Saturday, and neither she, nor Laura, worked on the weekends, so she guessed her friend was out for a jog, or maybe running errands.

While both of them had tried adopting a healthier diet (which neither of them had stuck to), and practicing yoga (which had become a part of their routine), Laura had also taken up jogging.

The fool had tried to coax Jess into joining her, but though Jess was sporty, she’d had no interest in becoming a runner.

She’d let her bestie enjoy that particular activity alone.

Jessica plugged her phone into her car, and a Maroon 5 song started coming through the speakers. She pulled out of her parking spot, and started home. It being a Saturday, more cars were on the road, but despite the busier traffic, she got back to her place in good time - thanks to the fact that she excelled at weaving around slower drivers. She took pride in that skill.

She let herself into her apartment, stepped out of her flip flops, dropping her purse and keys on the table by the door. Eagerness for the night ahead had her heading for her bedroom, where she immediately started going through her clothes, looking for something to wear for dinner.

She’d nixxed several outfits, set two possible options on her bed when her phone buzzed in the back pocket of her jean shorts.

If she hadn’t been expecting to hear from Laura, the ring tone her friend had chosen for herself, would have given away who was calling her.

“Hey.” she answered.

“Hey.” Laura echoed. “I just saw your text. So...” her friend said excitedly. “... he changed his mind?”

“He did.” Jess replied, smiling into her closet as her friend responded with even more excitement.

Laura asked what had changed his mind.

That was a very good question. One Jess didn’t have an answer for. She didn’t know why he’d changed his mind, she was just glad that he had.

“At first, he said he didn’t think us getting together was a good idea.” she told Laura. “Then, when I was leaving, he suddenly changed his mind and he asked me out to dinner.”

“Ohhhh.” Laura exclaimed with happiness for her. “Where are you guys going?” she asked.

“Rigatoni’s.” she replied, flicking hangers right to left, nixxing more outfits.

“Oh, nice.” Laura said appreciatively.

Coming to the end of the line of her potential outfits, Jess turned back to her bed, to the two dresses she’d laid across it.

“What do you think I should wear?” she asked Laura. “I’ve narrowed it down to that red dress with the black belt, or that mint green dress I bought the last time you and I went shopping.”

She was leaning more toward the mint green dress herself. It was more... flirty than the red one.

“The mint green one.” Laura voted immediately. “That colour looks great on you.”

Her own choice seconded by her friend, Jess hung the red dress back up in her closet, then went over and hung the mint green dress on the back of her bedroom door.

With Laura in her ear, asking her more questions about her visit over to Henry’s, demanding all the details, she headed out of her room, padded down the hallway to the living room where she got comfortable on her sofa, supplying answers the whole way.

“I wonder what made him change his mind.” Laura mused after she’d finished telling her how Henry had called after her when she’d been leaving.

“Me too.” she said.

When he’d called after her, he’d really surprised her. She’d gone from pretty damn bummed, to pretty frickin’ happy in the space of a heartbeat.

While she and Laura continued talking, she turned on her 42" LG and started flipping through channels. Finding nothing on regular TV, she went into Netflix and threw on a comedy, keeping the volume low while she talked with Laura.

“Call me when you get home tonight.” Laura requested near the end of their conversation. “I can’t wait to hear how it goes.”

“I will.” she promised.

Laura laughed softly.

“I can’t believe you’re going out with Henry.”

She let out a laugh of her own.

“Tell me about it.” she said.

As much as she wanted to go out with him, a part of her still couldn’t believe she was.

“I’ll talk to ya later.” she said, and they hung up.

She checked the time on her screen before setting her phone on the seat cushion beside her. It was almost three. She had a bit of time to kill before she’d start getting ready.

She turned the volume up on the comedy she’d put on, tried to get into it, but the show was more background noise than anything else, her thoughts too preoccupied with Henry. As excited as she was... she was also nervous.

What if things were awkward between her and Henry tonight? This would be the first time in a long time that they’d be alone for more than a few minutes.

They’d been such good friends at one point, but that had been years ago. And in the years since they’d been friends, Henry had kept her at arms length, annoying her with his barbs and poking. What if their date tonight fell flat?

Jessica’s stomach clenched.

The fact that Henry had secretly liked her for so long was added pressure.

She was just... her. She had her good points and her bad, like anyone else. What if, after pining for her for so long, Henry was disappointed by the reality of dating her? What if spending more time with Henry revealed they were incompatible?

They’d been close as kids, but they’d grown up, maybe they didn’t have anything in common now. Maybe all they had was a physical attraction. And maybe the only reason Henry’s feeling had hung on so long was because he’d believed he couldn’t have what he wanted.

Jess tried to shake off her nerves, but... she was having dinner with Henry - her former childhood buddy... her personal menace (up until a few weeks ago)... so as if she was going to be successful.

Not only did she fail in shaking off her nerves, when she started to get ready, those nerves climbed to a higher level of jittery.

In her bathroom, she did her hair and makeup. She plugged in her straightener, and while it heated up, sectioned her hair, clipping the top half up. After a few seconds, the red light on her FHI went from blinking to steady, and she started adding soft waves to her hair, doing the underneath, then letting down the top half she’d clipped up, and doing that.

Once she had a beach wave look going for her, she started on her makeup. Keeping it simple and natural, she lined her eyes with brown eyeshadow, brushed on a couple of coats of mascara and applied a neutral color to her lips.

Done with the Maybelline, she left the bathroom, headed into her bedroom, and changed out of her T-shirt and shorts, and into her dress.

In the front hall, she grabbed her beige purse, and matching beige sandals out of the closet. She slipped on the shoes, adding two-inches to her height, transferred her wallet, keys and phone to her purse, and was on her way.

To Henry - the boy who used to keep her in stitches with his antics... the boy who had hurt and confused her when he’d pushed her away.

As she drove to the restaurant, things she hadn’t thought of in years, things she hadn’t let herself think of, because they’d made her miss Henry, came to mind. She was knee deep in memories and nostalgia by the time she pulled into Rigatoni’s parking lot, and spotted Henry’s F-150.

Though the windows were tinted, she could tell the cab was empty. Her eyes went to the front of the restaurant, searching him out. She found him standing on the sidewalk near the entrance, looking down at his phone.

A fresh shot of nerves hit her in the belly, seeing the boy she’d just been remembering, as he was now.

A man.

A very handsome, attractive man.

He didn’t look up and Jess took her eyes off him, tried to quell her nerves as she drove around looking for a spot. She pulled into one half way down the line of cars. Getting out, she locked her Hyundai with a beep and started toward the entrance of the restaurant, and Henry. As she closed the distance between them, his head lifted and he took a glance around. His gaze landed on her and, seeing her, a smile spread across his face.

Meeting his gaze, an answering smile came to her lips. Something shifted inside her and her stomach quieted a little, her nerves fading a little.

While the two of them were entering new territory tonight, he was still... Henry. And she found comfort in their familiarity.

He tucked his phone away, watched her approach, the summer sun shining down on his face.

“Hey.” he murmured, when she drew close, stopping in front of him.

“Hey.” she echoed, smiling up at him.

There were both quiet for a moment.

“You look beautiful.” he murmured.

Her insides warmed at his words and she thanked him, gestured to him with the hand clutching her purse.

“So do you... I mean...” she let out a little chuckle. “...you look... very nice.”

In the dark-colored button-down shirt and tan slacks he had on, he looked like a model straight out of one of those men’s high-end clothing catalogues... all sexy and handsome and suave.

In her opinion, anyway.

“Thanks.” he echoed with a cute quirk of his lips.

They stood there for a few moments, like two shy teenagers on their first date, unsure of themselves, before Henry cleared his throat, suggested they go inside.

Jess nodded.

Henry acted the gentleman and held the door open for her, following her into the restaurant and over to the hostess stand.

Two young women, Jess guessed both to be in their early to mid twenties, one blonde, one brunette, smiled at them.

“Table for two?” the blonde asked.

At their ‘yes’, the brunette grabbed two menus off a shelf behind her.

“Right this way.” the brunette smiled, and started deeper into the restaurant, leading them around tables, the majority of which were occupied.

As she and Henry followed, Henry’s hand settled lightly on the small of her back. His touch, the warmth and weight of his hand on her, sent tingles up her spine.

No guys Jess had dated in the time since her last relationship had ended had given her tingles, or any of the other feelings Henry had been causing in her lately.

That Henry was the one to end her dry-spell in the guy department was so unexpected... and so wonderful.

Their hostess stopped at a small table for two, waited for them to sit, and Jess mourned the loss of Henry’s touch as they took their seats across from one another.

The brunette set their menus on the table in front of them.

“Your waiter will be with you shortly.” she told them, and left, returning to her post at the front of the restaurant.

Jessica set her purse at the edge of the table, her gaze touring the restaurant... taking in the dark walls, the tables covered with crisp, white tablecloths, the romantic lighting... before settling on Henry, meeting his eyes across the table.

Her thoughts slipped back to the last time she’d been to Rigatoni’s.

“I haven’t been back here since that night I saw you with Trixie.” she mused.

The night she’d been stood up.

“Neither have I.” Henry said, his gaze drifting around them before returning to her. “That seems like so long ago.”

She nodded.

It really did.

She chuckled softly.

“If someone had told me then,” she said. “... that I’d be here with you now... on a date...” she chuckled again, shook her head. “... I would have laughed in their face.”

Henry nodded, let out a chuckle of his own, nodding in agreement.

He seemed about to say something else, but was waylaid by the arrival of their waiter, a handsome, thirty-something man, with blonde hair and a warm smile.

“Hello. My name’s Will, I’ll be your server tonight.” he introduced himself. “Can I start you with some drinks?” he asked, looking back and forth between them.

Henry deferred to her.

Jess already knew what she was going to order - more often than not, when she ate at Rigatoni’s, she had the garlic shrimp pasta - so she ordered a white wine that would pair well with it.

“I’ll have a glass of the Pinot Grigio.” she requested.

Will nodded, shifted his gaze to Henry, who ordered a glass of red wine for himself.

Will gave another nod. “I’ll be right back with your wine.” he said and started away.

Henry picked up his menu and opened it, glanced across the table at her when she didn’t.

“Already know what you’re going to have?” he asked, brows lifted in question.

“Mm hmm.” she confirmed. “The garlic shrimp pasta.”

“Mmm.” he mused, considering her choice. “Their garlic shrimp pasta is really good.” he said, clearly undecided as to what he was going to order.

His gaze returned to his menu, his eyes quickly scanning through the options.

“But, I think... I’m going to have... the butternut squash ravioli.” he decided.

He closed his menu, set it on the table, lifted his gaze to hers.

Neither of them got a chance to say anything else just then because Will reappeared, tray in hand. He set two tall glasses of ice water down in front of them, then two empty wine glasses. Two small, glass carafes were left on his tray, one Jessica’s white wine, the other Henry’s red.

Once Will had poured their wine, he asked if they were ready to order.

“We are.” Henry confirmed, and again, deferred to her.

“I’d like the garlic shrimp pasta, please.” she ordered politely, handing Will her menu when he extended his hand for it.

“And for yourself?” Will asked, gaze shifting to Henry.

“I’m going to get the butternut squash ravioli.” he ordered, also handing off his menu to Will.

“Excellent. I’ll go put in your order.” Will smiled and left them.


After Will left, Henry’s gaze returned to Jessica.

She looked even more beautiful than she had that night she’d been stood up... her hair down, soft and sensual... her eyes and lips accentuated with the barest touch of makeup.

She reached for her wine, eyed him over the rim of her glass as she took a small sip. He could tell by her look that she wanted to ask him something.

“What?” he asked, smiling at her speculative gaze, inviting her to share whatever was on her mind.

She set her glass down, licked her lips, drawing his gaze to her mouth.

“I’m curious...” she murmured. His gaze lifted, met hers once more. “... over the years... you must have thought about telling me how you felt...” her words trailed off.

He nodded.

“I did.” he murmured.

Of course he had. He’d thought of telling her how he felt hundreds... thousands... of times. Had come close... really close... to saying something when she’d been with her last boyfriend, Alex.

“I almost said something when you were with Alex.” he confessed now.

“Really?” Jess asked, this information seeming to intrigue her.

He nodded. Propping his forearms on the table, he leaned towards her.

“When you were with him... I was dying with jealousy.” he admitted. He huffed out a laugh, thinking of Alex. “I really wanted to hate that guy. But he was so... nice.”

Which he had found so... annoying.

Jess nodded, a fond smile reaching her lips. “He was. That’s why it took me so long to break up with him.”

Henry had been so surprised when he’d learned of their split.

And relieved.

“Why did you break up with him?” he asked now.

Jess gave a little shrug. “That ‘spark’ was gone.” she paused. “He started to feel more like a good buddy, than my boyfriend. Ya know?”

He nodded in understanding.

Mirroring him, Jessica laid her forearms on the table, leaned towards him.

She had that look in her eyes again... had another question for him.

“I gotta ask...” she began. “... you said you didn’t think it was a good idea for us to get together... what made you change your mind?”

The vision of himself as a lonely, old man, full of regrets flashed in his mind. He blinked that image away. Feelings, long contained, swelled inside him.

“I need to know...” he murmured, his gaze steady on Jess. “... if we could... have something. I don’t want to regret not trying.”

His words put a soft smile on her face.

“Me too.” she said, voice quiet. After a beat, she added, “I’m glad you changed your mind.”

His breathing changed... pleasure and happiness altering how much oxygen he needed.

“Me too.” he echoed.

Their gazes held, a new intimacy curling and melting into the energy between them.

Jessica’s smile turned teasing after a moment.

“Although,” she drawled, drawing out the word, head cocking to the side. “I have to admit... I am annoyed with you. I think of all those years, you keeping your feelings secret, and being such an asshat...” she shook her head, obviously thinking him an idiot.

He quirked a grin.

“I gotta admit...” he said. “... it was fun bugging you.”

Jessica snorted, gave him a ‘no shit’ look.

“Yeah, you seemed to be enjoying yourself.” she said, shaking her head at him.

He laughed.

“C’mon.” he cajoled. “Like you didn’t have fun dishing it back at me.”

She ‘hmmm’d’, sat back, raising her wine to her lips.

“You zinged me good, many a time.” he continued.

A proud grin slowly took her mouth. She took a sip of her wine.

“I did, didn’t I?” she agreed, setting her glass down.

She definitely had.


Joking with Henry, Jess felt her nerves fading away.

It seemed she needn’t have worried about it being awkward between them.

It wasn’t awkward.

It was nice.

Really nice.

Nostalgia eased them into their evening, their conversation seasoned with a lot of ‘remember when this...’ and ‘remember when we..’ while they waited for their food.

All their reminiscing made the time it took for their food to arrive feel like no time at all.

Jess sat back when she spotted Will approaching their table. Warning them that the plates were hot, he set their dinners in front of them.

“Is there anything else I can get you?” he asked.

She and Henry both smiled a polite ‘no, thank you’.

With an ‘enjoy’, Will was gone.

Alone again, the two of them started into their meals, picking up the thread of their conversation where it had been paused.

Finishing a bite of her pasta, Jess smiled, another memory surfacing. A funny moment that she’d completely forgotten about.

“Remember that time... we were swimming at the cottage...” she said, fork held above her plate. “... and a fish swam up your trunks and tickled your...” she paused, selecting a term. “... worm.”

She chuckled at the memory of Henry squirming as his dangly bits were nibbled.

Henry chuckled with her.

Their laughter subsided after a moment, but the two of them continued smiling across the table at one another.

A lovely contentment enveloped Jess. The years of missing her friend seemed like nothing now... the two of them picking up their relationship right where they’d left it.

And now... there was this new element between them.

This attraction.

This desire.

Desire was something Jess hadn’t felt in a long time, was something she’d never thought she’d feel for Henry. But she did. She wanted him. Wanted to know what it would feel like to kiss him.

Her gaze dropped to his mouth, a mouth she’d never thought of as sensual before, but here she was, thinking just that.

Would he kiss her tonight? She hoped so.

While she and Henry ate, conversation turned from the past to the present. They talked work, and sports, and other interests - some of which they shared, and some they did not.

Josh came up at the end of their meal, while they were waiting for their bill.

Knowing Henry was worried about her brother’s reaction to them dating, Jess had assumed they’d be keeping the fact they were seeing each other quiet... at least until after they had a couple of dates under their belts, and they knew if they were pursuing this thing between them farther than that.

Her assumption was confirmed when Henry asked her if she’d mind if they didn’t tell Josh about them, at least for a little while.

She readily agreed, since she didn’t care if her brother knew or not, and since it would put Henry’s mind at ease. It was her opinion, he was worried needlessly, but feelings weren’t attached to logic or reason.

Will brought them their bill, which Henry wanted to pay alone, and Jess let him. After all, he had been a pain in her ass for years. He escorted her to her car, the two of them stopping by the driver’s door and turning to one another.

The cars she’d parked between were gone. The parking lot, full when they’d gone into the restaurant, was more than half empty now. The sun had begun its descent toward the horizon, the summer evening slowly winding down.

In the fading light, she met Henry’s gaze, smiled.

“I had a really good time.” she murmured, tucking a piece of hair behind her ear.

Henry’s gaze dropped to her mouth, before meeting hers once more.

“Me too.” he murmured.


Though tempted to ask Jessica back to his apartment for coffee, Henry didn’t. He didn’t want to give her the wrong impression, have her thinking he was hoping to get physical tonight.

He wanted to, of course. Years of pent up desire had him ready and eager. But this was - technically - their first date, and though he could be selfish at times, he didn’t want to rush Jess.

He’d be more than happy with a kiss tonight. He watched Jess, hoping she’d give him the green light for that kiss and his heart picked up speed when she did a second later. Her gaze dropped to his mouth, her tongue snuck out to wet her lips.

A clear invitation.

He swallowed.

He’d wanted his first kiss with Jessica to have a more romantic setting than a parking lot...

... but where they were didn’t matter... being with her, made wherever they were, perfect.

After years of wondering what it would be like to kiss her, he was about to experience it. He was about to find out how soft her lips were, how they felt pressed against his own. He was about to find out how she tasted.

He swallowed again, his heart trying to beat its way out of his chest.


When Henry stepped into her, Jessica stepped into him, her hands - one empty, one clutching her purse - floating up, coming to rest lightly on his chest.

Her pulse started thumping faster and her breath caught as he lowered his mouth to hers.

She tipped her head to receive his kiss. Her eyes drifted closed as his lips pressed against hers, gentle at first... seeking... slowly becoming more firm.

As their kiss deepened, all she could think was...


Just... wow.


Henry’s fantasies paled in comparison to actually kissing Jessica.

Her lips were soft as petals. Her taste was ambrosia (with a hint of garlic from the pasta she’d had).

He couldn’t get enough.

He raised his hand, cupped the side of her face, gently tilted her to a better angle. He couldn’t resist taking the kiss deeper, licking at her lip, seeking access to her tongue. Jessica’s lips readily parted under his.

The first intimate stroke of their tongues had him groaning quietly.

Their kiss spun on, slow and sweet. A moment, an experience, he’d wanted for so long... and would now, never forget.

When at last, they parted, his heart squeezed at the hum of a sigh that escaped Jessica, at the dreamy look in her gaze when their eyes met.

“When can we get together again?” he asked, his voice deeper than it had been moments ago.

Still looking at him dreamily, she replied. “I’m free any night, except for Thursday or Friday.”

“What about tomorrow?” he asked.

“Dinner with the fam.” she reminded him.

“Right.” he nodded. Duh. “What about Wednesday?” he suggested. “You could come over to my place? I could make you a nice dinner?”

“You can cook?” she asked, feigning amazement.

“Yes, I can cook.” he replied, giving her feigned amazement a dry look, the corners of his mouth lifting.

“Alright.” she smiled, accepting his invite to his place on Wednesday. “I’ll brave your cooking.” she teased.

The affectionate smile she gave him, had his heart squeezing again.

“I’ll text you.” he promised.

Though he and Jess never texted each other, they had each other’s contacts thanks to Josh needing to use Henry’s phone to text Jess when his own phone battery died.

“Okay.” she replied.

After a moment, she got her car keys out, unlocked her car with a couple of beeps and a flash of tail lights.

“Good night.” she murmured.

“Good night.”

He watched her get in her Hyundai and drive away, before starting for his truck, a new bounce to his step from all the happy he was feeling.

If he were a cartoon, he’d have had hearts circling his head right then.

Wednesday couldn’t come around fast enough as far as he was concerned. He’d see her before then, at the bakery, but Josh would be there.

A smidgen of his happiness chipped away at the thought of his best friend... guilt pricking him.

He hated to sneak behind Josh’s back with Jessica, but wanted to keep what was between him and Jess, between him and Jess, for now. He wasn’t in a rush to find out how his friend would react to him dating his sister.

Hopefully, he’d be for, not against.

Sorry, Josh... he mentally apologized to his friend, sending that out into the universe...

... I just couldn’t resist her anymore.


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