Betting Jessica

by Deanne Wilsted

  Jessica jumped up from the couch and pulled out her college crate from under the piles of books on her bookshelf. She shuffled through it, casting aside the many company brochures she had collected during campus recruiting, until her hand landed on the final project she had created in her Junior year sociology class. Vacantly she stared off into space as she held it on her lap. She knew what was inside, but it had been a long time since she had opened it up, and she wanted to feel again the sense of accomplishment she had experienced putting it together.

  She glanced down at the large ‘A’ scrawled on the top cover, and at the teacher’s note: Jessica, bravo! You pulled together a complex issue and made me understand the story behind it. It is clear that your organizational skills helped you draw together a wide set of facts, and the photo album (not to mention the yummy treats for the class) gave us all a sense of the lives behind these people. I expect great things from you, no matter what you do after graduation.

  Jessica realized she was crying and swiped the tears off her face with the back of her hand. Her great things list had begun going downhill during senior year, when it had become obvious that she would have to sacrifice dreams for paychecks. Now, two years and four jobs later, her chief accomplishment was moving to a new metal desk. She sighed and laid her head on the edge of the crate. When had she become so lost? She needed something new, she realized; something that would force her to approach her life completely differently.

  Suddenly the bet, ridiculous as it was, didn’t seem like such a silly idea. Maybe it would be what she needed to break herself out of her rut. Certainly it met the criteria of being totally different from anything else she was doing with her life.

  And, while it might be crazy to take this on, the sociology project reminded her that she could do anything she set her mind to. It shocked her to realize that these people, her friends, might not know that side of her. Did they simply see her as a total flake?

  She tried to think about the bet in a different, more realistic light. Assuming she could actually meet Ian Drake, was there a chance she could get him to ask her out? It was a possibility. At least, it wasn’t exactly out of the realm of possibility.

  She thought she had been pretty cute in college, though now she was admittedly a little too close to the average-American weight. But her hair still had a nice bouncy curl to it and her fair face was still fresh and clear, most of the time.

  For sure she would have to change the way she dressed though. She hadn’t cared how she looked in a while; probably about three jobs ago. So now her style was a mix of poor college student and grandmother. On the positive side, though, her Dad had been pestering her to dress better, so maybe he’d pitch in some money if she swallowed her pride and told him she wanted it for clothes.

  The sheer superficiality of the bet made her laugh. But the truth was Jessica knew she needed an overhaul. Assuming she lost weight and changed her style, was there a chance Ian might ask out a nice, fun, cute but not famous girl? She’d read enough about him to know he liked blondes. Okay, blonde models, but maybe he’d be ready for a normal everyday sort of blonde girl. After all, she seemed to remember his last few relationships had ended badly.

  Bottom line, she didn’t have any chance at winning this bet unless he actually met her in person, and to do that she would need to have a solid plan. Smiling, Jessica acknowledged one more advantage in her favor—planning was her very best talent.

  And this wasn’t about dating a celeb; this was about setting a difficult goal and reaching it, sticking to something and giving it everything she had. She sat down to do some serious planning. It might take a month or two years, but one way or another, Jessica knew she was going to get a date with Ian Drake!

  She re-listened to Erik’s message and her face glowed with newfound excitement and determination. Oh really Erik? She thought to herself. You think I can’t date Ian Drake? We’ll just see about that.

  Chapter Four

  Jessica yawned and stepped into the shower. She hated Monday mornings in general, but after working late into the night on her project plan, she was especially sluggish today. The only thing that cheered her was the idea of stopping for coffee. Thanks to hitting the snooze button about eight times, no matter what she did at this point she’d be late. But she knew it was wishful thinking. And so, twenty minutes later as she waited for her bus to arrive, she accepted the fact that a stale tortilla filled with mystery cheese would end up being her breakfast.

  Her snort earned her a few stares from her fellow passengers. She hadn’t had time to search for something better in her fridge, but in any case, she doubted she would have found anything no matter how much time she had spent staring into the empty white appliance. The marketing gurus needed to come up with some sort of breakfast food that would magically appear in people’s fridges, since the very people who needed grab-n-go items like her forgot to shop for them.

  Jessica jumped off her bus and looked longingly at Starbucks as she rushed toward her office building. She tried to console herself with the thought that the money she saved could go into the ‘Date Ian Bet’ savings jar (DIB for short) she had created the night before. The thought of all that she had accomplished brought a smile to her face.

  She glanced at her watch and tried to maintain her positive outlook even as she entered the abyss; also known as Higgen’s Insurance Company. The lobby of the building had always reminded Jessica of entering the water through the hole of some sort of submergible sea craft. It was dark, murky, and cold; most of all you just knew you were about to spend your day drowning!

  She pushed her way to the elevator banks and juggled her stuff as people pushed around her. One of the main reasons she liked getting to work early was so she didn’t have to deal with all of the nine o’clockers. Who were these people anyway? And how on earth did they get to show up for work this late?

  Looking at the stack of papers on her desk she realized she already had a pile of work left for her by her manager. On the very top of the pile was a note reminding her to attend a special meeting which, in fact, had started thirty minutes earlier. Oops. Better to skip it at this point.

  Giving up all hope of a productive day, Jessica finally finished her report and decided that she had earned an actual lunch hour. She shocked Becky with her phone call to meet up and grabbed her coat to leave before anyone could give her more work to do.

  The best part about her new desk location in the marketing department was that when she really wanted to escape she could be into the elevators and on her way out of the building in less than two minutes. The downside, of course, was that she was actually, technically, located in a hallway. But, better to see the positive side of things, right?

  It was the act of an unjust God, then, that her boss stepped out of the elevator just as she was getting ready to jump in.

  “Oh Jessica, just the person I was looking for. Now, don’t you worry about the meeting this morning; I covered for you, said you had had to pick up some dry-cleaning for me on your way into the office. I can’t make excuses for you all of the time though, so try not to miss the next meeting, right?”

  Figures, Jessica thought. His idea of covering for her was to make her out to be his personal secretary. The idea had merit, actually. It seemed like mostly what she was going to be doing anyway so why not give her that title? Of course, if he changed her title he wouldn’t be able to have her direct the editorial team, write the advertising reports and manage the budget.

  She missed most of what he said during her reverie and only caught the tail end where he was concluding with “…not one of management’s better ideas, but I’m sure you’ll find a way to break it to the team. You call me if you need some back-up.”

  Yeah, right, she thought. In the one week she’d worked for him already it was clear he’d told his real secretary, Kathy, to screen her calls.

  “Sure, Mr. Jackson, I’ll plan a team meeting,” Jessica answered. “But, you know, just to make sure I have all my fac
ts right, would you mind having Kathy send me a quick note with the details? Okay, better run, I’m already late for my lunch date.”

  And with that, timing it perfectly, Jessica was through the just closing elevators doors. If people looked at her oddly for pressing the lobby button about twenty times, so what. She was not going to stick around and hear what Jackass had to say about her actually going out for lunch.

  Chapter Five

  The café where Becky and Jessica had agreed to meet was exactly the right distance from Higgens that Jessica knew no one would be there from her office.

  God it was nice to be out. Why didn’t she do this more often? Of course, one of the problems with going out to lunch was that it was really difficult to motivate herself to go back. It was one of the reasons she tended to simply eat at her desk.

  She saw Becky through the window as she rushed to the door. Becky, being about six feet tall, was actually rather hard to miss. She had one of those gorgeous athletic bodies that made it seem like she was about to take off in flight at any moment. And her face was as animated as her body. Her wide mouth and eyes allowed her an amazing number of different expressions…and she tended to use all of them in every conversation. She had pretty normal, shoulder length brown hair and sort of hazel eyes, but could still completely capture attention just through her personality.

  Becky was getting ready to order, having finally decided Jess wasn’t going to show up after all, when she spotted her walking through the front door.

  “Oh Jess, I had decided you weren’t coming. What happened? No, don’t tell me, Jackass, huh? Man, his timing is impeccable. If I didn’t know better I would think he had a camera trained on you the way he keeps showing up just as you are getting ready to leave your desk for any reason.”

  Jessica held up her hand to stop the stream of consciousness that Becky was famous for, but the gesture didn’t even slow her down.

  “So, what’s up? What’s the special occasion that calls for a real lunch out? Oh no, you’re not going to quit again, are you? You can’t! I mean, you just got promoted.”

  Jess had to laugh out loud at the word promotion and finally cut in. “Yikes, Beck…give me a second to order, will you? What are you having?”

  Jessica looked up from her menu to find Becky studying her and gave a self-conscious laugh.

  “What? Don’t tell me I need to cut my hair again? That last time was a nightmare and it’s only now finally recovering enough to look, I think, cute.”

  “Oh no, Jess,” Becky reassured her. “I totally agree. I was thinking how great it looks right now, sort of cute and pixie-ish. And it makes your eyes look even bluer.”

  Count on Becky to make a good day even better.

  “So, are you going to tell me why you have such a huge grin on your face?” Becky demanded.

  Having been put off already, Jessica could see she was going to have to get straight to the point. For some reason telling Becky her plan scared her a bit. She really counted on Becky’s support in general and she wasn’t sure what she would do if Becky was skeptical or even worse, laughed at her. So, without meaning to, Jessica hedged a bit rather than coming right out with it.

  “So, Becky, you know I don’t have any hard feelings about Friday night, right?”

  Becky nodded hesitantly.

  “Good! Because I hate it when we fight; I soooo count on you.” Jessica took a sip of water and tried to think through how to say what she wanted.

  “Well, one good thing came out of that whole miserable night…”

  “Really, what?” Becky laughed. “Seems like things are worse than ever between you and Erik; and the rest of the group have decided you have finally lost it altogether.”

  “Oh! Thanks, Beck. Don’t hold back on my account or anything.” Jessica grimaced and Becky started to apologize but Jessica held up her hand to stop her. “No, no, no, that’s okay. I guess that’s the point I’m getting to here. I barely blame them for feeling like that. But the thing is, Becky, what makes everyone so certain that it’s impossible?”

  Jessica was so focused on getting her plan out that she totally missed the look of horror that crossed Becky’s face.

  “I mean, really, he’s just a guy like anyone else. Perhaps his job puts him in the public eye, but I bet underneath that he wants the same things we all do.”

  “Yeah, maybe so. I’m sure he’s like any of our friends. I mean, he must be a friend to someone,” Becky finally said.

  Jessica took a breath. “Exactly! And, well, I’m tired of being discounted and overlooked by everyone. So,” Jessica cleared her throat, “I’ve decided to see if I can’t win the bet and prove everyone wrong about me.”

  Jess watched Becky’s napkin fall off her lap and thought she heard, “Shit, shit, shit!” while Becky was under the table retrieving it.

  “What was that?” Jess asked suspiciously.

  “What?” Becky asked, annoyed at getting caught.

  “I thought you said something.”

  “Oh, no. I was just swearing at my napkin.”

  Jessica still wasn’t convinced, but continued. “Anyway, as I was saying, I may not get far; but I’m going to see whether a smart, nice, sort of successful, well okay, maybe not successful, but hard working girl like me can’t catch the interest of someone like Ian Drake.”

  Becky was quiet for so long that Jessica started to get a bit concerned. And she couldn’t read Becky’s normally expressive face, which was even more worrying. She took a bite of food to keep herself from saying all the scary thoughts running through her head: You don’t think I can do this, do you? You’re going to try to convince me this is stupid. You don’t really want to be friends anymore with someone who is this crazy.

  Jessica was so caught up in her negative spiral she almost dropped her fork when she finally heard Becky speak.

  “Jess, you know what, if anyone can do it, you can. You’re right! You are smart and successful, no matter what you often may think. And, on top of all that, I noticed you left out totally cute. Heck with Ian Drake, why don’t you try to get Brad Pitt or something?”

  Jessica was so relieved by Becky’s response she broke down into tears.

  “Oh no, Jess, I mean it, really. I’m totally behind you,” Becky said.

  “I kn,kn,know y,you are.” Jessica hiccupped and tried not to be overwhelmed by such an unconditional show of support. Not many people had stood by her in her life, not even, or perhaps especially not, her own family. How could Becky ever understand what that kind of confidence meant to her? She shook her head and smiled tremulously. “I know you are,” she repeated.

  Over their salads Jessica and Becky talked about her plans.

  “You know, Beck, I appreciate your sentiment about Brad, but the thing is it’s not only about dating a celebrity. You know I’ve always had a crush on Ian, and even if he weren’t a star I would still be interested in dating him.”

  Becky laughed at the understatement. “I know, I’ve been here, remember? I’ve heard you talk about Ian for the last three years.”

  “Exactly,” Jess said. “If it was simply about proving I could date a celebrity I don’t think I could actually convince one to go out with me. I mean they probably get that all the time.”

  “Yeah, they’re called stalkers.” Becky giggled.

  “Exactly,” Jessica agreed. “He just seems like such an interesting guy, perhaps a bit intimidating for having dated all those models, but still someone I think I’d like to get to know. That’s not crazy, is it?”

  “No, Jess, not at all. Besides, you’re totally normal…in a good way, you know. I’m sure he’ll be flattered.”

  Jessica pulled out her project plan, cracking Becky up. “I should have known you’d have it meticulously planned out already. Is there a line item there for when you introduce Ian’s cutest friends to me?”

  Chuckling, Jessica said, “Laugh if you will, but a good plan is my best shot at actually winning this bet.” She started to show
Becky some of the key steps involved.

  “You know, it seems like an awful lot to do. Like, the research I understand and going to his favorite vacation spot is a particularly cool idea. It’s just…” Becky hesitated as if unsure what to say, and then quickly rushed on. “You already have a lot going on with the new job and everything. Are you sure you are up for such a huge campaign?”

  “You know, Beck, everything I do in this bet will be totally for me, and I can’t tell you how freeing that is. I think it will give me a healthier perspective on my life in general.”

  Becky relaxed again and smiled as she glanced at her watch. “It already has. I mean, look…you’re sitting here completely laid back at 1:30 enjoying…wait…”

  Frantic now, Jessica began throwing her plans back into her bag and reaching for her coat.

  “Oh yeah, Jess, it’s done you a world of good,” Becky mumbled to herself. She grabbed Jessica’s arm to slow her down for a second. “Tell you what, Jess, make it through the week, finish your plan, and I’ll come over to your apartment Friday night so we can do some online research together. Hey, maybe we can even start making our vacation plans, that is, if you won’t mind me tagging along.”

  Jess reached over and gave Becky a quick kiss on the cheek. And as she ran out of the café she realized that for all of her grousing about her life she was blessed with a best friend.

  Chapter Six

  Jessica checked her recipe and tried not to get spaghetti sauce in her hair as she pushed some stray bangs off her forehead. The music played softly in the background, and between that and the warmth of the kitchen she felt totally relaxed. Relaxed that was until she heard a “hey” out of the blue and ended up flinging red sauce across the floor as she spun around to see who was there.

  “For God’s sake, Becky, you scared me to death.”

  “Sorry. Sorry,” Becky held up her hand apologetically. “I didn’t want to bother you so I let myself in.”