The Dating Itinerary

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by Brooke Williams


  Excitement bubbled up in her as she realized that her assignment could lead to a cover story. As long as she found a man she could call her boyfriend by the end of the columns. Penny drew back the ball and let the momentum of its weight thrust her forward as she neared the end of the lane. With an expert flick of her wrist, the ball went careening down the middle of the alley, headed right for the center pin.

  “How do you do that?” Di asked behind her. She was third in line but always last in the bowling department. It didn’t seem to faze her, but everyone else enjoyed ribbing her about her lack of talent in the area.

  Penny smiled as her sisters began to chatter. The ball hit the middle pin soundly, and the others fell around it, leaving just one in the right corner still standing.

  “You were robbed!” Nic shouted as Penny turned on her heel and stepped back to the edge of the lane. Her ball popped up in front of her as she dried her hand on the nearby blower.

  “I’ll get it this time,” Penny promised. And she did.

  As the others took their turns, Penny got to hear about Nic’s most recent conquest. Though she was still technically single, she never had a shortage of dates. It was likely because of her sunny personality and gorgeous blond hair. They said blondes had more fun, right? And in her case, it was true. At least where men were involved. Though in the end, it never worked out with any of them.

  “His name was Michael, and he kept bragging about being an agent. But when he first came up to me, he said, ‘Has anyone ever told you that you have blue eyes?’ And I said, ‘Uh, yeah, only every time I look in the mirror.’” Nic burst into laughter, and the sisters all joined her. She always had the best stories about men coming onto her. It happened every day, just walking down the street, like clockwork. No man could resist her long legs, golden hair, and sparkling eyes. “Despite the bad opening line, we had a good time together.”

  Penny leaned in when Di told the group about the latest project she was working on in the construction world. She didn’t have a job that was common for a woman, and Penny admired her for that. She couldn’t build a birdhouse to save her life, but she was thankful that women like Dime existed to work in unique industries and show the world women were capable of anything.

  Q didn’t have much to report, but Penny knew it was just a matter of time. Her youngest sister might be small, but she could talk the ear off an elephant if she put her mind to it.

  When the first game ended and the girls ordered drinks and appetizers from the bowling alley snack shack, Penny saw her chance. She didn’t want to get interrupted by someone’s turn.

  “So, I have some news,” she began with trepidation.

  “It’s about time,” Di exclaimed. “What’s his name?”

  Her sisters giggled behind their hands and exchanged knowing looks. They all knew how Penny felt about dating. She’d been hurt one too many times in the past, and part of her wanted to give up on men completely. But her sisters never let her, and their hope for her finding someone spurred her on, at least sometimes, that she could possibly meet a special man someday.

  “I don’t know yet, but hopefully, I will soon.” Penny tested a secretive smile on the group. It worked. Her sisters exchanged questioning looks as Q urged her to go on.

  “I have a new assignment at the magazine.”

  Di sighed. “Are you covering the local fundraiser ball again?” she asked. Construction was her business, not magazine articles. While Di couldn’t imagine dressing up to attend a formal event just to write a story on it, Penny was fascinated by anything that was article-worthy. If there was a story, Penny wanted to find it and present it to the city with words organized just so.

  “No,” Penny shook her head, “though I’d definitely attend again this year if they invited me.”

  Di rolled her eyes.

  “Out with it already, Pen,” Q encouraged. “What’s this new assignment?”

  Penny grinned. “It’s called ‘The Dating Itinerary,’ and it means a feature column for weeks!”

  “Wow, that’s so great! Congratulations!” Nickel threw her arm around Penny and hugged her from the side.

  “Wait,” Di said slowly, putting the pieces together. “‘The Dating Itinerary?’ What do you have to do?”

  “That’s the thing.” Penny grimaced. “I’ve been assigned to try different dating avenues all around the city. You know, things like speed dating, a matchmaker, going to the bars, that sort of thing.”

  “You get to go on dates?” Q exclaimed, clapping her hands with glee.

  “Not get to, Q, have to,” Penny corrected. She watched her sisters exchange looks, and Nickel elbowed Dime in the ribs.

  “Okay, so you go on dates…and then what?” asked Nic.

  “I write about them. Not about the dates, specifically, but the way I got the dates, you know, to give advice to other people in the city as to what might work for them.”

  “Wow,” Di said, “that sounds like the perfect job for you.”

  Penny narrowed her eyes at the veiled sarcasm in her sister’s voice. “I know I’m not the smoothest when it comes to men, but this is a good opportunity for me.”

  “Yeah,” Q agreed. “You’re bound to find Prince Charming with one of these ways of dating.”

  Penny shrugged. “That’s the thing. I kind of have to.”

  Her sisters frowned in unison.

  “If I meet someone and, you know, become a couple by the end of the feature, the magazine said they’d put my story on the cover. I get a chance to really prove myself, you know?”

  “Oh, Penny, you’re good as gold as a writer, and you know it,” Nic encouraged.

  “And the right guy is out there. You’re sure to find him,” Q continued.

  “Thanks. I’m really hopeful that everything will come together. I want everyone at the magazine to know I got this gig because of my writing chops, not because I’m the only single person on staff. But I also want to prove that I can follow through. Plus, I really do want to find someone.”

  “So what’s the first dating adventure going to be?” Di asked.

  “Well, it was actually last night…and it was speed dating.”

  “Ooh, I’ve always wanted to try that,” Q exclaimed. “Can you take me next time?”

  “I only have do each thing on the list once. I’m afraid you missed your shot.” Penny laughed as Q snapped her fingers.

  “Is speed dating where you have like a minute to talk to each person?” Nic asked.

  “Two, actually, and believe me, it was more than enough for some of those guys.” Penny rolled her eyes.

  “Does that mean you’re still single?” Q asked.

  “Um, yeah, for now. But I made some connections. There was this one guy who had a Star Trek T-shirt that was to die for. Oh, and this other one who was unemployed and lived with his mom.”

  “That good, huh?” Di shook her head as the sisters enjoyed a laugh over the dating failures.

  “But there was also this guy named Pete with bright orange hair…” Penny liked to draw it out and make her sisters wait.

  “You guys would have cute babies,” Nic stated.

  “That’s what he said!” Penny exclaimed.

  “Wait, really?” Di made a face.

  Penny nodded. “Yeah, but it wasn’t as weird as it sounded. He’s actually a nice guy. I wouldn’t mind seeing him again.”

  “So the night ended on a high note, huh? Success already. This dating itinerary thing might be your path to love—and the magazine cover.” Q fixed the knot on her shoe and prepared for her turn.

  The smile slid from Penny’s face as she thought about how the night had actually taken a turn after Pete left her table. “I ran into someone I knew, too,” she said in a quiet voice.

  “Was it Josh?” Q asked. “Please tell me it was Josh.”

 
Josh was the football player Penny had dated in high school. Q always had a crush on him, though she never admitted it. Josh had gone off to play at an Ivy League school, and Penny had gone her own way to begin her writing career. Things had ended amicably, but Q never forgot him, apparently.

  Penny smirked. “No, it wasn’t Josh. Worse. Much worse.”

  “Well, come on, don’t leave us hanging,” Nic encouraged.

  “George Monais.” Penny spoke through her teeth.

  “That guy from your magazine?” Di asked.

  “Not just any guy,” Nic spoke in a hushed voice. “The one who stole her job.”

  “Right out from under her,” Q added. “And he didn’t even deserve it.”

  Penny waved her hand. They could bash Geo all night long, but it wouldn’t help anything. They’d had plenty of conversations about him when the tides had turned at work and it became apparent that he was getting the job she wanted over her—just because the editor at the time had a crush on him.

  “What was he doing there?” Di asked.

  Penny shrugged. “Dating, I guess. I have to admit, it was a shock seeing him. I don’t exactly remember the conversations I had after talking to him.”

  “Ooh, how did that go?” Nic started. “Did you tell him where he could go?”

  “Not in so many words. We only had two minutes, you know.”

  “How long does it take?” Di asked. She began listing all sorts of ways to say it. Working in construction had given her colorful options.

  Penny let her sisters take the conversation from there. Their easy banter made her forget about the fact that in a few short days, she was going to appear on TV to talk about her speed dating experience to promote the feature and the magazine. She had to immerse herself in the very dating world she had avoided in recent years—and she had to find someone. During this process, she was going to try every dating app, avenue, website, and path. If there was a tried and true way to love, Penny would find it.

  …

  “So I went to the Speed Dating thing last night,” Geo said to his agent over the phone.

  “Yeah, and how’d it go?”

  Geo shrugged. “It was okay. I got lots of numbers.”

  Smathers chuckled. “Yeah, you did. This is your big chance. If you can make this feature fly, no more hopping from paper to paper, story to story. It would be your own column every week. And the network TV show to go along with it? Man, you’ll be rolling in the dough.”

  Geo nodded. He’d been writing freelance for newspapers and magazines all over the country for the past three years. Michael Smathers was a well-known agent and had approached him to represent his interests. When he first told Geo about this opportunity, he wasn’t so sure about taking it. Leaving St. Louis for a job in New York would mean moving away from his sister. But when he heard the bottom line of the offer, there was no way he could pass it up. If he made that kind of bank, he could infuse cash into his sister’s charity. It’d be a way of making up for the past. And this dating list column? It was like an audition for the network. A pass/fail sort of thing.

  “I’m telling you, Geo, this is your ticket to success,” Michael went on. “The country is crazy for love, and if you’re able to find it in one of these ways, it’ll go viral.”

  Geo sighed. That was the key to everything…going viral. No one could make it anywhere without that anymore. Writing about love was catchy. And he was the most eligible bachelor in the region. He’d been named as much in the local newspaper.

  “And once you get settled in New York, you’ll start traveling for the TV program. You’ll get to see the world, man, and cover stories you’d only ever dreamed about.”

  When Geo first spoke to his agent about the offer, he’d wondered why the network channel was interested in him at all. But Michael had told him they wanted to try something different. Geo would write weekly columns, and the cameras would follow him on his quest for the story. People who watched the show would read the columns and vice versa. It was a win-win for everyone. The columns would be syndicated, the show national, and Geo a big star. But only if he was able to create pure gold through the dating list idea.

  “Are you going to tell me where you got this idea? This ‘Dating List’?” Geo asked.

  “A little bird told me about it. Let’s just leave it at that. A reporter never reveals his sources.”

  Geo wasn’t going to press the issue. For now. He heard the sly tone in the agent’s voice. It was better if he didn’t know. He had plausible deniability that way. The ends justified the means, in this case. Geo was in it for the greater good, after all.

  “Well, I got plenty of leads, so now I just have to pick a woman to call and see if I can get a date.”

  “Have some confidence, man. Of course you can get a date! Any of those women would be lucky to get your call.”

  Geo shook his head. Smathers was nothing if not good for his ego. He supposed it was part of his job.

  “I’ll email you with the details on the other dating avenues. Oh, and I got you an appearance on the local TV news show Monday morning.”

  “Okay.” If it took a few dates to put him on the map for good, he’d go with it. Geo checked his watch. “I gotta run. I’ll send you the speed dating article soon.” He hung up and grabbed his jacket. It was uncle time.

  Twenty minutes later, Geo knocked on his sister’s front door. Her house was small and rundown, but it was hers, and she was proud of it. He heard the screams before the door opened.

  “Uncle G!” Eliot threw himself around Geo’s ankles.

  Geo laughed and picked the boy up. “That was quite an entrance. How’s my little man?”

  “I met a girl at school this week, and we’re going to get married. I asked, and she said yes.”

  Geo made a face. “I thought girls were gross.”

  “That was last week.” Eliot slid his sticky fingers through Geo’s hair. “Your hair’s too long. You should cut it. Mommy said so.”

  “Oh, she did, did she?” Geo stepped into the living room, and his nephew slid down his body like it was a pole. His heart always felt full the instant he saw the little guy.

  Maggie appeared in ragged jeans and a T-shirt. “I did say that. You’re looking shaggy there, G.” She slid a jacket on and grabbed Eliot as he attempted to jump from the nearby couch. “You sure you’re up for this?” she asked as she rolled the squirming boy from her arms to his.

  “Of course. I’ll have him worn out and in bed by eight.”

  Maggie rolled her eyes. “Good luck. I’ll be home by ten.” She gave Eliot a peck on the cheek and tousled his hair. “Be good for Uncle G, okay?”

  “Kay!” The boy stiffened. “Lift me, Uncle G, lift me!”

  Geo started doing reps, using Eliot like a weight bar.

  “Who did you say was going to wear out who?” Maggie asked as she quickly closed the door behind her.

  Geo set his nephew down and winked at him.

  “How did people get around before there were cars?” Eliot asked as he picked a toy car up from the carpeted floor.

  Geo shrugged. “I guess they rode horses.”

  Eliot’s eyes widened as he turned to his uncle. “Wow, did you ride a horse, Uncle G?”

  Geo blinked. “How old do you think I am?”

  Eliot’s face grew serious. “I don’t know. Like, really old.”

  “That’s it, you’re in for it now.” And so began a wrestling/tickling match to end all wrestling and tickling matches.

  After four matches, three snacks, two cartoons, and at least forty books, Geo tucked his nephew in. He glanced at the clock—nine forty-five. He brushed Eliot’s hair from his forehead. Something about the sleeping child warmed his soul. He smiled and let himself watch his nephew sleep for a few extra minutes. He was one lucky uncle.

  Chapter Three
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  A few days passed, and Penny hadn’t heard from Pete from the speed dating event. She knew it was the “in” thing to wait a couple days before contacting someone you were interested in, so there was still hope. She could use the number she got and reach out first, and she would have—if she hadn’t lost the little sticky notes the woman in charge had handed over. As she sat at her desk, staring at the blank page before her, she needed inspiration to start her article. She thought about the dim lighting in the room, the women wearing too much makeup, and the strange variety of men.

  Could Mr. Right be just two minutes away? she typed. She smiled at the opening line, hunkered over her keyboard, and started writing.

  “How goes the dating?” Josie from marketing stuck her head in Penny’s office door.

  Penny finished her second sentence then turned to Josie, glad for an excuse to stop her work on the article. “It’s going.” She sighed.

  “That well, huh? Does that mean we won’t be hearing wedding bells any time soon?” Josie leaned on the doorjamb with crossed arms.

  “Wedding bells? I’ll be lucky to hear my phone ring.”

  Josie made a face. “Well, keep at it. You never know. Maybe Mr. Right really is out there, and maybe, just maybe, you’ll find him in one of these places.”

  “I have to.” Penny glanced at the sheet on her desk that listed the dating avenues she had to try in upcoming weeks. Speed dating…check. Tinder…an online matchmaker…the list went on. She’d be just as likely to find a man at the end of the line at the store, bagging her groceries, than she would in any of these ways. But she needed to make this work. Her career would take a big step with a cover feature.

  “I guess we’ll see, won’t we?” Penny shrugged. She didn’t want to reveal her pessimism to Josie, but it was hard not to come across as glum when her phone remained alarmingly silent.

 

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