The Dating Itinerary

by Brooke Williams

  “If nothing else, it’s bound to be entertaining.” Josie waved a hand and chuckled as she left.

  Entertaining? What did that mean? Did everyone around the office think no one could possibly fall for Penny? She shook her head. It didn’t matter what anyone else said. She was going to crush this assignment. Better than that. She was going to knock every man who came across her path onto his backside. Starting now.

  Penny turned back to her computer and started typing so fast her fingers could barely keep up with her thoughts. Her renewed confidence soaked into the story she was creating as a smile curled her lips.

  The annoying buzz of her phone sounded on the desk beside her, snapping her out of her writing glaze. She glanced at it and noted that a text had come in before she resumed typing. She couldn’t let anything distract her now that she had a flow going. When she got stuck on the second paragraph, she picked it up to give herself a break.

  So, there’s a connection here, huh, pretty little Penny? the text read. The number wasn’t one that was in her phone already. “Pete?” she whispered, a slow smile spreading across her face. He’d told her she was pretty as a penny, after all.

  It was quite an evening, wasn’t it? she asked with a smiley face emoji following her quick sentence.

  You can say that again.

  Penny decided to take the initiative. If she was going to have a happy ending to her first story, she needed to see Pete again. And soon. Maybe he could join her in the cover story at the end. Who knew? When can we do it again? she asked, her fingers shaking as she hit the send button. Pete was nice enough, and he deserved a chance longer than two minutes. First dates were always awkward, especially with a strict time limit in place. Second dates only got better…or so she hoped.

  A bubble popped up on her screen to indicate he was typing then disappeared. Penny waited, staring at the screen for a response. The bubbles didn’t reappear for a full minute. He’d contacted her, right? So he must want to see her again.

  I wasn’t expecting you to say that.

  Penny frowned. Had he hoped to just text each other, chat by phone, flirt a little, and get to know one another that way? It was a somewhat modern, even romantic notion, but she needed to be face-to-face with a man to see if there was actual chemistry. She could enjoy a phone conversation with a brick wall if she had to. She got that skill from Nickel. Plus, she needed material for her article—and fast.

  Well…what do you think now that I have?

  Penny crossed her fingers. She’d have a lot more depth to her article and more complimentary things to say about speed dating if she could walk away from the experience with at least one second date. Since Pete was the only man who wanted her number, besides Geo Monais, which was surely a joke, she couldn’t play hard to get.

  I’m up for it if you are, he replied.

  Penny pumped her fist in the air. She was feeling inspired to get back to the article, but she wanted to cement things with Pete first.

  Coffee after work? she asked.

  I’m always up for a good brew. What time?

  Five. The shop on Mission…It’s Always Morning Somewhere.

  Got it. See you then.

  Penny ended the conversation with a waving hand emoji and set down her phone. Yes! She had much more to say about speed dating now. Maybe what she found to be a silly way to find love really worked for some people. Whether or not it would for her was yet to be explored, but at least the possibility was there.

  …

  George frowned at his phone, scrolling back up through the conversation with Penny. He had to admit, it was the last thing he expected when he pulled up his old contacts from the magazine and sent her the first message. He’d had a few dates over the weekend, and one of the women’s shirts had a silver sheen to it, which reminded him of Penny. While the dates had been pleasant, no one gave him trouble like Penny had at the initial event. He liked the way she had an answer for everything he had to say, sarcastic or not.

  When he shot the text to her, he expected some kind of glib comeback with every ounce of sass she could muster. He remembered working with her well, and though he had received the promotion over her despite her hard work, she wasn’t a woman to be trifled with. He knew the second he left the magazine, the job would be hers, especially since the editor who hired him over her in the first place left the month before he did. He’d even tried to turn the promotion down, but the raise in salary and profile had been too convincing in the end, and he wanted to help his sister, even in little ways. After he realized he could do even more in the freelance world, he took his leave. And once he was out the door, what he predicted was exactly what had happened—and Penny deserved the promotion.

  Geo had never been able to admit that to her, though. He was good at what he did, too, and just because the managing editor hoped for a relationship with him didn’t mean he had to give up the position for someone else—and he hadn’t, though he’d tried unsuccessfully a few times to pass on the job out of fairness.

  What made him reach out to Penny in the first place? Was it that none of the other women appealed to him during the speed dating event or after? Was it the way her confident green eyes glowed underneath the dim light? The way she wore the little bit of makeup on her eyes and lips with a self-conscious flair? Or the short hair he was dying to touch to see if it was as soft as it looked?

  They’d had a good time together when they’d partnered up in their writing ventures at the magazine, before they were vying for the same position. Once he got the job over Penny, she gave him looks like he’d killed her puppy, and she wouldn’t listen to a word he said. Geo would have loved the chance to explain. Penny might have even joined him in his quest. But she never allowed it. Her hate ran too deep, and he had to move forward. Now, he needed more for his dating column, and perhaps she was the road to his success. He wanted to add something other than a few mundane dates. And she already had a deep dislike for him, so he wouldn’t be chancing anything there.

  Geo didn’t want to intentionally take advantage of her a second time around—he hadn’t even done it on purpose the first time—but hey, if she was willing to see him, she was asking for it. She knew their history better than anyone else—other than him. If she wanted to see him again, who was he to turn her away?

  Chapter Four

  Penny sat in the It’s Always Morning Somewhere coffee shop, sipping her caramel mocha drink. She didn’t allow herself fancy drinks often, but on special occasions—and a second date was certainly that, if nothing else. Maybe she should have waited for Pete. But sitting alone at the corner table, it gave her something to do with her hands. She didn’t look as much as if she was waiting for a date, who seemed to be a bit on the late side.

  The bell on the front door clanged gently as it opened, and the barista scurried out from the backroom, looking for the customer. Penny raised her eyes from her warm drink and caught sight of broad shoulders and floppy hair. “Geo?” she muttered. Of all the luck. He caught her gaze and lifted a hand in her direction. She rolled her eyes and waved a few lackluster fingers in return as he moved to the counter and ordered.

  Why did he have to wander in here, of all places? And of all times? She glanced out the nearby window for Pete. Geo might recognize him, and he might even approach their table to make jokes. He’d probably ask Penny how his job was going, as if he did something nice for her when he bowed out of the magazine business and set out on his own. Yes, he was the last thing she needed on her date.

  Penny took another look at her watch. Where was Pete? He’d seemed eager to meet. How late was fashionably late? Penny thought back to their string of texts when an uncomfortable notion began rising in the pit of her stomach. She dug her phone out from her purse and inspected the number attached to the texts on the screen. It didn’t indicate who the message came from, of course, because it wasn’t someone who was already on her contact l
ist. But that didn’t mean it was Pete, either. For the first time since Geo left the magazine, Penny wished she hadn’t deleted his contact in her phone.

  What if it wasn’t Pete who had contacted her at all—but Geo? Why would he? It wasn’t like they had ended their stint as co-workers well, and she hadn’t exactly been smooth during their two-minute so-called date. Why would he have bothered to get her phone number at all—and then use it? He might even still have her number in his contacts, but it didn’t make sense for him to reach out to her now, after months had passed and they had both moved on in their professional lives. She had an excuse for receiving his phone number. She’d circled every name on the list, though she’d certainly tried to scratch his out. He couldn’t possibly think she was interested since the lady matched them up mistakenly—could he?

  She drew her attention to the counter, where George was receiving his drink as the barista handed it over, a lovesick smile on her face. He returned the smile and sauntered away from the counter—in Penny’s direction. The woman had probably given it to him for free. And instead of writing Geo’s name on the cup, she likely wrote her own phone number.

  Penny sat up straighter in her chair. What was she going to do? It was too late to run. There was nowhere to hide.

  “Miss Coyne.” George set his drink on the table and pulled out the chair, turning it around so he could sit in it backward.

  “George.” Geo might suit him better than George, given his classic good looks and muscles, but that didn’t mean Penny had to use the new nickname.

  “If I had a penny for every number I got that night…”

  Penny scoffed. “Let me guess, you’d be a rich man.”

  “Not exactly.” George rubbed the back of his neck with his hand. “But I could trade them in for a quarter.”

  Penny had already had enough of his ego. “What’s this about, George? Why’d you want to see me?”

  George frowned. “If I remember correctly, you’re the one who mentioned meeting up.”

  Penny sighed. He was right. But that was when she thought he was Pete.

  “My mistake,” she admitted. “I thought you were someone else. I deleted your number from my phone ages ago. Why did you agree to this?”

  “I can see that there’s still some tension between us.” Geo leaned forward. “Can’t we just let bygones be bygones? You know, maybe start over as two people who happened to meet while speed dating?”

  “What’s in it for you?” Penny asked. If there was one thing she knew about Geo Monais, it was that he didn’t do much unless he got something out of it.

  Geo shook his head. “Harsh. Isn’t it enough that I get to have a nice chat with a lovely woman, a pretty little Penny?” He winked.

  Penny tapped her fingers on the table. Ah yes, Pete had said she was pretty as a penny, and Geo had called her “pretty little Penny.” The difference was subtle, but she wished more than anything she’d picked up on it in the text conversation. She could have gotten around this awkward meeting altogether.

  Geo could have called anyone from that event, and yet he’d contacted her. Granted, he may not have expected she suggest they meet, but he didn’t have to agree to it. Why had he?

  “Why were you there that night?” she asked, still digging for the truth.

  Geo leaned forward, as if he didn’t want the barista or the other patrons to hear. “I like to try new things. It was something I hadn’t done before. So, why not?”

  “You were just bored, huh?”

  “Nah, I’m never bored.”

  Penny rolled her eyes. “Right, because the ladies line up for you wherever you go.”

  Geo chuckled. “Is that what you think?”

  “What’s on the cup, Geo?”

  Geo turned the cup around in his hand. “My name.”

  Penny squinted. She had been wrong. Just a name, not the barista’s phone number. “Why did you want to meet me today? I asked you here by accident, but what’s in it for you?” She didn’t want to admit to being wrong about the cup. Instead, she was going to try and steer the conversation away from her mistake.

  He shrugged. “I don’t know. A whim, I guess.” He waved a hand in the air. “When I texted, I assumed you’d blow me off. When you suggested we meet, I figured, why not, you know? We may not have gotten along well in the working world at the end, but we did once. Plus, we’re not in that world now, right?”

  He had no idea Penny was working on dating stories, and that was the whole reason she was sitting across from him now, though he was supposed to be Pete. Penny now knew that Pete wasn’t going to show up. Perhaps she’d contact the woman in charge of speed dating to try and get his number again. But for now, George was here. Time was of the essence, and if she couldn’t get ahold of Pete and set anything up yet this week, Geo could be her only shot at giving the story closure.

  “You aren’t what I expected.”

  “What did you expect? That I’d want to rehash our old feud?”

  Penny thought of Pete with his bright red hair. “No, I just…”

  “It’s okay, you don’t have to explain. I know how I came off back then.”

  “And at the speed dating event…”

  Geo chuckled. “Okay, even then. That’s just a persona. There’s another side to me. I’ll prove it to you.”

  …

  Geo smiled and laid on the charm. Usually, his good looks and a few cheesy lines was all it took to get on a woman’s good side. They would often recognize his name from the papers or a piece they’d read somewhere else in the past, and that was that. Penny was different. She didn’t buy into any of that, and he had to act like a different person. Someone he knew from his past—the real George. She wouldn’t believe anything else. He had already been on a few easy dates with women from the other night, but he was in for a challenge with Penny. And he liked that idea. He could relax and be more of himself with her than with anyone else he’d seen.

  “So all I ever really wanted to do was throw stuff.” Geo opened up a new conversation track.

  “Throw stuff?” Penny asked.

  “You know, in track. I was good at shot put and discus, and I even went to state. I thought I was good enough to make the Olympic team someday.”

  “What happened?”

  Geo shrugged. “I started noticing girls a bit more, training less. And then I got bit by the writing bug.”

  George was taking her on a tour of his history. He wanted her to see him as sincere—someone with a past. They only shared a piece of his story, not the whole thing. If she could see past their shared history, perhaps he could make some headway with her and reform her opinion of him. She’d never allowed him to explain before, but if he could get her to see him in a different light now, perhaps they could be friends again. He’d genuinely liked her before their rivalry began, and going back to that friendship status would be more than okay.

  “All I ever wanted to be was a flag girl,” Penny commented softly.

  “Like in the band?”

  She nodded. “But it turns out they don’t have a career for that. Once you’re done with college, that’s pretty much it.”

  “So that’s when you started writing?”

  “I’ve always written.” Penny wrapped her hands around her cup and took a sip. “I just never thought I could make a career out of it, you know?”

  “But you thought flagging would be a good option?”

  Penny giggled as Geo half-stood and whipped his hands around in the air as if he were twirling a flag. “Okay, maybe not.”

  “I think you ended up just where you were meant to be.”

  She narrowed her eyes. “Is that so? I always assumed you thought I took over the position because you, the golden boy, were gone. They chose you over me the first time around, right?”

  Geo didn’t want to bring up the hu
rt he knew she felt, but since she had broached the subject, it was an open door. “But you were the one who deserved it all along.”

  Penny frowned. “Thanks, George,” she said in a soft voice.

  He was getting to her. He could tell. She was softening toward him. But the weird thing was, he was enjoying it, too. Geo was just being himself, and it was a nice change of pace. He didn’t have to put on an air or pretend to be puffed up. Plus, he found Penny’s short hair and bright eyes adorable. He just wished she hadn’t been so angry with him before.

  “Since we crossed paths at a dating event, it’s only fair that you tell me about your first date.” George leaned forward in his chair, interested to hear what life was like for Penny before they met.

  Penny stared off into the distance. “My first date ever?”

  Geo nodded, watching her bring up the memory.

  “Let’s see. I guess it was when I was fifteen. My parents dropped me and my sisters at the mall, and I met up with Edwin from school.”

  “You dated a guy named Edwin?”

  “What? He was cute! Like George is any better?” Penny laughed.

  Geo held up his hands. “You got me there. So what did you and Edwin do?”

  “Went to the arcade. He bought me a game of Miss Pac Man, and then we held hands by the prize counter.”

  “But things didn’t last,” Geo supplied.

  Penny sighed theatrically. “He moved away the next year. And the rest…is history.”

  Geo shook his head. “Who knows what could have happened?”

  “What about you? I can’t be the only one doing a deep dive on dating history.”

  “My first date.” Geo stroked his chin with his fingers. “I suppose it was Samantha. No, Claire. Definitely Claire.”

  “The head cheerleader?” Penny teased.

  “Oh no, we didn’t have cheerleaders in elementary school.”