Chapter 5

CHAPTER 5

Haleigh flopped down on her bed, then balanced her phone against a stack of books so she could see the screen. She pillowed her hands under her head as she waited for Jack to pick up.

Her mind had been buzzing since she’d left her mother’s house that afternoon. No one had brought up work or dating again after they’d left the grocery store, but Haleigh was still frustrated. Even after all the examples she’d shared, neither her grandfather nor her mom had seemed on board with her sabbatical idea.

Beyond setting them up on their own dates (which, though fun in theory, was not really feasible), she didn’t know how to give them an actual glimpse into her experiences. Or how a particularly bad date could sink its claws into her self-esteem and tear it asunder.

But no one was a more top-notch schemer than Jack. He’d reminded her of that on Monday when he pretended to be her mom to save her from that awful date with Annie. And when you added Haleigh to the mix, backing him up, they were unstoppable. There had been that time, senior year in college, when they’d devised a plan to catch the package pirate terrorizing Haleigh’s apartment complex through an intricately placed series of whoopie cushions. Or when they’d “accidentally” locked Macy Lunden in the supply closet so she couldn’t sing her own rendition of “On My Own” and steal Haleigh’s first-place trophy at the middle school talent show.

She needed that version of Jack tonight.

He answered her video call on the ninth ring. Drops of water glistened in his light brown hair and pooled around the constellations of freckles on his bare shoulders.

“Sorry, I was in the shower.”

Haleigh should have known. He always showered after dinner, and it was seven thirty. “Crap. I should have looked at the time.”

“No duck, no fowl.” He grinned lazily. She’d stopped correcting this favorite saying of his a decade ago. “What’s up, buttercup?”

God, he was a dork. And that only made him hotter.

Haleigh had never really understood lust at first sight. She could tell when someone was aesthetically pleasing, sure, but for her to truly want them, she needed to learn who they were. What made them tick. The secret sides of themselves they didn’t always share with the rest of the world. That was sexy.

Which explained why she was so far gone for Jack. There was no part of him she didn’t know as well as she knew herself.

“Remember when we were talking the other night about my grandfather chaperoning my dates?”

Haleigh heard the creak of his bed as Jack settled down. “Indeed.”

“What if we actually made that happen?”

His thick eyebrows dipped. “You probably need to ask Roger…”

“Not literally. But the essence of the thing.”

“What’s going on?”

Haleigh burrowed her face into her pillow and groaned. “My mother tried to set me up with a teenager at the grocery store today.” She turned back to the screen so Jack could see her. “These people have to be stopped.”

“Geez, Christine, not jailbait.”

“Right? I need some way for them to understand what it’s like so everyone will get off my case.”

Jack’s hand rubbed at his cheek. The bristle of his stubble against his palm was another shot of comfort to Haleigh’s veins. He fussed with it all the time, but refused to shave for fear of being carded for his baby face until he was fifty.

“Maybe Logan could help you with some spy cameras?” he suggested.

Logan was Stanton’s cameraman on On the Plus Side and one of the producers. They hung out enough that Haleigh might almost call him a friend. Or as much of a friend as anyone that grumpy can be, anyway.

She pursed her lips. “That has to violate some kind of privacy law.”

“True.” She could hear Jack drumming his fingers against the mattress. His eyebrows pulled together, then he shook his head.

“What?” Haleigh pushed. They were brainstorming. There were no bad ideas.

“What if they picked the dates or something?”

“Picked the dates?”

“Yeah.” Jack was smiling now. His mastermind grin. “Like some kind of dating show.”

“We are not pitching this to Stanton.” Good god, Haleigh did not want to imagine how her roommate would produce a show about her love life. It would be mortifying. She’d have to move to a new country afterward. Dye her hair. Create a new identity. Learn to enjoy peas and raisins so no one would believe it was her.

“As much fun as that sounds, no. I mean, let them take the wheel and find you ‘better’”—he threw air quotes around that last word—“options.”

Haleigh sat up and tugged a pillow to her chest. “You want me to have Pépère set me up with his buddies from the VFW?” She wasn’t convinced her grandfather knew anyone more than ten years his junior, besides her and Joey. “And for Mom to go back to the market for the jailbait?”

Jack was clearly not on his game. Maybe it had been a long day at work. His job—something with medical billing and coding that made Haleigh’s head spin whenever he tried to explain it—seemed to forever stress him out.

“There’d be guidelines, obviously,” he said.

Haleigh leaned forward, angling her face closer to the phone. “And what happens if none of the dates work out?”

A bigger smile spread over Jack’s lips. “Then they have to leave you alone about dating. For at least six months.”

“No dating interrogations at all?”

“Complete silence.”

“A sabbatical.” This was a good idea. An A-plus Jackson Brooks scheme. “And I can go to Joey’s party solo with no grief.”

“Oh shit, that’s really happening?”

Haleigh settled back against her headboard. “I have about three months to find someone I’d want to spend an entire long weekend with surrounded by my family.”

“All the more reason to kick this plan into gear.”

“So I can prove to them that dating sucks.” Haleigh pumped a fist in the air.

She pulled a notebook and pen from her bedside drawer and waved it at him. “Let’s establish some rules.” She flipped to a blank page and scratched out a heading: Date-pocalypse. Let the chaotic end to her disastrous dating life commence.

Staring down at the page, she fiddled with the chain of her key necklace. “How many dates should Mom and Pépère get?”

“Well, wait.” The rhythm of Jack’s tapping grew louder. “Maybe it shouldn’t only be them setting you up. Broaden your scope. Show you’re really putting yourself out there.”

Haleigh studied his face. He looked so serious. A part of her feared that he was pushing this for a reason. Was he dating someone and too afraid to tell her?

But that would violate Rule Number Three: no hiding if either of them started dating. He’d come up with that one.

Haleigh wiggled her body in an attempt to loosen up. This was her anxiety and nothing more. Her brain was always quick to jump to catastrophe.

She sighed. “Okay. Fine. Stanton would definitely want in, anyway. And obviously Joey.” Her sister would have fourteen cows if she wasn’t included, even if the last thing Haleigh wanted was to find out what kind of person Joey thought she should be dating. “Anyone else?”

This felt like a good list. They’d all bring different kinds of dates to the table. It would help Haleigh prove that even with a larger pool of eligible people, finding her person could still be borderline impossible.

Jack cleared his throat.

“What?”

He cleared his throat again.

“Get yourself some water.”

He rolled his eyes. “Good lord, you’re oblivious sometimes. Me.”

“What about you?”

“I want to be on the list.”

Haleigh grabbed the phone so she could stare more closely at the screen. “You’ve been holding back potential dates for me?”

“You know my coworkers are mostly middle-aged women.” The medical insurance industry apparently wasn’t teeming with people their age.

“Maybe that’s my problem. Maybe I need to date more middle-aged women.”

Jack laughed. “I don’t think they could handle you.” From anyone else, Haleigh might be afraid that was an insult. “Seriously, though. I want to help.”

Haleigh pursed her lips.

“Hey. Rule Nine.” We are allowed to voice opinions about significant others, but only if they’re objective (i.e., no being jealous assholes). That had been one of Haleigh’s, to save Jack (and herself) from his sometimes questionable taste in women.

So why did he invoke it now? Was he hoping to set her up with someone real? Did he know she still wasn’t over him and this was his way of getting her to move on?

She sighed. “Fine.” She could never refuse Jack anything, but if he was going to be one of the five horsepeople of the date-pocalypse, he needed to get on board with her actual goal: a hassle-free dating sabbatical.

She added his name to the bottom of the list. Her eyes skimmed over her notes.

“I’m thinking two dates per person? It gives a margin for error,” she suggested.

Jack nodded. “And ten’s a nice round number.” He was a big fan of round numbers. He thought they were predictable.

Haleigh could see it. Patterns were reliable. Safe in their own way.

She sat back against her pillows. Her body was alive with electricity. She’d been so frustrated for so long that it felt good to be taking the reins. Agency, her therapist would call it.

“Thanks, Jack.” She smiled at the phone. “I seriously don’t know what I’d do without you.”

He winked at her. “You’ll never have to find out.”

Haleigh hoped with every part of her that was true.

She was about to say good night when he yelled out, “Wait!”

“What?”

“You should make everyone fill out profiles for their choices.”

“Genius.” She loved a good dating profile. Anything that helped her learn more about the person before they met. She flipped the notebook to a clean page. “What do we think? All the usuals? Occupations, ideal dates, turn-offs? That kind of thing?”

He shook his head. “Make it quirkier. Questions they wouldn’t expect. Like, ‘Would you rather drive the getaway car for a friend or help them bury a body?’”

Haleigh laughed as she jotted the question down. “Forget your current job. You should start your own dating service.”

He grinned. “Maybe I should. Jack of All Trades.”

“Jack of Hearts.”

“The Jack of Your Heart.”

Haleigh had to swallow back her reaction.

If only he knew.

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