Hundreds of What Ifs by Azlin
Summary: A series of connected 100-word drabbles, detailing Pam's regrets and missed chances. Begins pre-series, and extends through Casino Night.
Categories: Jim and Pam, Past, Episode Related Characters: Ensemble, Jim/Pam
Genres: Angst, Drabble, Inner Monologue, Romance, Workdays
Warnings: Adult language
Challenges: None
Series: None
Chapters: 40 Completed: No Word count: 4055 Read: 85249 Published: March 11, 2008 Updated: March 27, 2008
Story Notes:
I'm not really sure where this came from, but I'm enjoying it so far. I'll try to update frequently, but I know better than to make any promises at this point. ;)

1. Chapter 1 by Azlin

2. Chapter 2 by Azlin

3. Chapter 3 by Azlin

4. Chapter 4 by Azlin

5. Chapter 5 by Azlin

6. Chapter 6 by Azlin

7. Chapter 7 by Azlin

8. Chapter 8 by Azlin

9. Chapter 9 by Azlin

10. Chapter 10 by Azlin

11. Chapter 11 by Azlin

12. Chapter 12 by Azlin

13. Chapter 13 by Azlin

14. Chapter 14 by Azlin

15. Chapter 15 by Azlin

16. Chapter 16 by Azlin

17. Chapter 17 by Azlin

18. Chapter 18 by Azlin

19. Chapter 19 by Azlin

20. Chapter 20 by Azlin

21. Chapter 21 by Azlin

22. Chapter 22 by Azlin

23. Chapter 23 by Azlin

24. Chapter 24 by Azlin

25. Chapter 25 by Azlin

26. Chapter 26 by Azlin

27. Chapter 27 by Azlin

28. Chapter 28 by Azlin

29. Chapter 29 by Azlin

30. Chapter 30 by Azlin

31. Chapter 31 by Azlin

32. Chapter 32 by Azlin

33. Chapter 33 by Azlin

34. Chapter 34 by Azlin

35. Chapter 35 by Azlin

36. Chapter 36 by Azlin

37. Chapter 37 by Azlin

38. Chapter 38 by Azlin

39. Chapter 39 by Azlin

40. Chapter 40 by Azlin

Chapter 1 by Azlin
Author's Notes:
This chapter is set a few months after Jim moves to Stamford. It should be obvious how the timeline works for the rest of the chapters, but if something is confusing I'll try to clarify it with a chapter note. Enjoy!

 

The longer I think about it, the more convinced I am it will just never work out. We had our chance. I missed it. And now he's moved on. He's forgotten it all. I wish I could say I'm over it, but to be honest, I don't think I ever had a chance to really be in it, which has only made it harder to move on.

I can't stop torturing myself with all the hundreds of "what ifs" that keep cluttering up my brain every day. I had so many chances: looks, thoughts, little moments. If only I'd known...

 

End Notes:
Reviews are always welcome!
Chapter 2 by Azlin

"Hi, I'm here for the interview."

"Oh, right. Um, you're Jim?" She tried to reconcile the voice she'd heard on the phone with the man standing in front of her. For some reason she hadn't thought he would be so... cute.

"Yeah," he said, pulling her back to the present.

"Okay, well, Michael's in his office. It's that door there. And, uh, hey, good luck!"

"Thanks, uh...?"

"Oh, I'm Pam."

"Pam," he said, and though she'd never loved her name, something about the way he said it made it sound different--better. "Thanks."

Another smile, then he disappeared into Michael's office.

Chapter 3 by Azlin

Five minutes later, she was still thinking about him. None of the other applicants had made such an impression. It wasn't just his smile or his easy, friendly demeanor. There was something else, an instant connection.

She wondered why she couldn't sit still. What was it that kept urging her to interrupt them with some little thing? Anything to get her into Michael's office, to see how it was going, to see that smile again.

She didn't know. But she couldn't help but hope that Jim would get the job so that she could try to figure it out.
Chapter 4 by Azlin

"Pammy! Sign this boy up! He is da man!" Michael kept talking, but Pam was more interested in the bewildered look on Jim's face. She loved seeing a normal person's initial reaction to Michael being Michael.

"So, I'm assuming you tanked," she joked, after Michael left.

"Yeah. It was awful." He responded instantly, a small smile playing at the ends of his lips.

"That's a shame. I think you might've liked it here." She handed Jim some forms to fill out, and tried not to jump when his fingertips brushed her own. She didn't know what was wrong with her.

Chapter 5 by Azlin

"Yeah?" Looking down at the forms, he sounded almost shy. She wondered, momentarily, if he'd felt the same shock when they touched.

She answered lightly, "Yeah. Michael's just the tip of the iceberg around here."

He laughed outright.

"You think I'm kidding, but just wait."

"It can't be all bad."

He laughed again at her dubious look.

Sitting down, Pam tried to ignore the strange feeling in her gut. Their conversation had been relaxed... fliratious. Unbidden, a thought of Roy instantly halted her musings.

Jim finished the forms, said goodbye, and left.

Already the room seemed paler without him in it.

Chapter 6 by Azlin

Michael loved him. He wouldn't stop talking about Jim, his newest "team member." Jim was starting next Monday, and in the meantime Dwight was being completely unbearable to everyone. Obviously feeling threatened by Michael's enthusiasm for Jim, Dwight now spent most of his time trying to hoard all the existing clients for himself, ensuring that Jim would have to start completely from scratch.

As for Pam, she was just trying to stop replaying the last time she'd seen him over and over again in her head. Especially the look on his face as he laughed. It was a good look.

Chapter 7 by Azlin
Author's Notes:
Back to post Casino Night with this chapter.

 

What if I hadn't gotten officially engaged three months before we met that first day? What if Roy hadn't moved in with me three years before that?

What if I'd been strong enough to face the fact that I was feeling something I'd never felt before?

What if I'd known then what he would say?

What if I'd known that this was only the beginning? What if I hadn't been so sure that those strange feelings would all just go away? What if I'd known they would get harder, not easier, to ignore?

What if I hadn't been so incredibly clueless?

 

End Notes:
I'll add more later. Thanks for reading! Oh, and these aren't beta-d, so let me know if you notice anything amiss. ;)
Chapter 8 by Azlin
Author's Notes:
Back to the pre-documentary story

 

That Thursday Jim called. He had some questions for Michael, but chatted absently with Pam for a minute. Hearing his voice made her pulse accelerate a bit, and suddenly she realized how badly she needed to control herself.

It was just a crush. There was no way Jim was feeling it too, and even if he was, she was still engaged. To a good man, who really knew her, loved her. Roy had been with her for years.

Unwilling to entertain the thought of abandoning that stability, she knew she could be Jim's friend. Good friend, even. But nothing more.

 

End Notes:
Thanks for reading, everyone! I hope you enjoy this next batch. ;)
Chapter 9 by Azlin

He walked into the office Monday morning, and her breath caught in her throat. He had obviously dressed up, his suit and tie much more formal than what he'd worn last week. Roy had worn a tuxedo to his sister's wedding last year, but that image wouldn't come quickly to her. The comparison fell flat in the face of Jim's easy smile.

She reminded herself it was only a crush.

Michael was announcing Jim's arrival, but Pam needed to focus on something else--work, solitaire... Anything but the way she'd inexplicably lit up, when all he'd said was good morning.

Chapter 10 by Azlin

After his speech, Michael instructed Pam to show Jim around. Michael was late for a meeting with a customer, or he would've done it himself. Pam almost wished he would stay and do it anyway. But that was silly. She was going to be friends with Jim, so she might as well get used to talking to him.

"Hey."

"Hi."

"So, are you ready for this?"

"Sure. Why?"

"I just feel like you should enjoy this moment."

"Yeah?"

"Yes." She nodded. "Because you're never going to go back to this time before you met your deskmate Dwight."

Jim just smiled.

Chapter 11 by Azlin


"...and this, is Dwight Schrute."

"I am the top salesman here and I intend to remain so. Do not mess with me, Jim. I am warning you now."

"Wow. Uh, hi." Pam could tell Jim was fumbling, but Dwight was already back at his desk, typing rapidly.

She raised her eyebrows, indicating that she'd tried to tell him.

Jim responded in kind, widening his eyes in surprise. Then grinning guiltily as they silently laughed together.

There was something fascinating in his face. His expressions just instantly drew her in. Truthfully, she suspected she'd always be a little fascinated by him.

Chapter 12 by Azlin

Around eleven Jim approached her desk and asked if she had plans for lunch. She'd been too busy that morning to pack anything, planning to just grab something from the vending machines. Roy sometimes joined her for lunch, but lately he'd been more apt to go out with Darryl. She had to deal with Michael's whims, so her lunch schedule was more erratic; she could understand why they didn't always invite her.

"Um, I don't know. I usually just eat here." She realized that she hadn't mentioned her engagement. She wondered if Jim would still be asking if she had.

Chapter 13 by Azlin

 

"Come on, Pam," Jim said, jarring her back to the moment at hand. "It's just lunch, and it's my first day, so I'm buying."

"Really?" she asked, intrigued in spite of herself at the thought of going somewhere with him.

"Yep. The sky's the limit. Just as long as you can get it at Cugino's."

"Cugino's?"

"Is that okay? We can go somewhere else if you want." His thoughtfulness struck her, and she paused, automatically trying to remember the last time Roy had asked her where she wanted to go.

"No. I mean, no. Cugino's sounds great. Let's do it."

Chapter 14 by Azlin

What if I'd said no to lunch that day? Would it have made a difference at some point in the future? What if I had picked up on the fact that I was already starting to compare him to Roy? Why didn't I realize what that kind of comparing really meant?

What if Jim hadn't smiled as he handed me my coat? Or held the door for me as we walked out of the office? What if I hadn't noticed that disapproving glance from Angela as we passed her in the hallway?

Would everything still have turned out like this?

End Notes:
As always, reviews are welcome!
Chapter 15 by Azlin

They drove in near silence. His stereo playing softly, the only accompaniment to her increasingly cloudy thoughts. She still didn't know why she was reacting to him so strangely. Normally, she was quite shy. It was almost as if they'd already known each other for years.

Like the mirrors in her mind had always been reflecting him.

She stole a glance at him. The bright, midday sun was hitting his forearms right where his rolled-up sleeves gave way to bare arm. She felt her knees trembling a little bit, and laid her hands across them to make them stop.

Chapter 16 by Azlin

"How long have you been working at Dunder Mifflin?"

"About two years."

"Wow. And you're still alive?"

"So far, yeah. I think it helps that I'm a woman, so Dwight doesn't see me as a credible threat."

He laughed, his face lighting up in a way she hadn't yet seen at the office.

"So what do you do when you're not at work."

"Um, I don't know," she hesitated, somehow reluctant to share her art with him, worried that he'd find it stupid or just laugh at her. "Actually, I like to draw."

"Really?" he responded enthusiastically. "That's awesome, Pam!"

Chapter 17 by Azlin

The lull in the conversation was nearing awkwardness when she looked up and caught him staring at her. Somehow this look was different from all the others he'd given her in the week or so since they'd met.

There was something fundamentally different in his eyes as they focused so intensely on her. He was still smiling softly, but with a seriousness that seemed out of place in a casual friendship. She tried glancing down at her plate and then back up at him again, but he was still looking at her. And then suddenly she couldn't look away either.

Chapter 18 by Azlin

She could feel herself beginning to blush under his gaze. With a jolt, she remembered that Jim was just her friend, that she hardly knew him. And Jim knew nothing about her. How could he? They'd only spent a few hours together. Her eyes averted, she toyed absently with the necklace she always wore.

"Um. So do you have a girlfriend?"

"What?" His voice sounded startled, like that was the last thing he would've expected her to say.

"Are you dating anyone?"

"Oh. Uh, no. I'm not."

"Oh."

Her brow furrowed slightly, anticipating what he would say next.

"Are you?"

Chapter 19 by Azlin

His question seemed just as focused as his gaze had been a moment earlier. She kept her eyes on the table as she answered so she wouldn't have to see his reaction.

"Um, yeah. Well, I mean, I'm engaged, so, yeah."

"Oh."

"Yeah."

"Really? I mean. I didn't see a ring or anything..." he trailed off, and she realized with a start that maybe this hadn't just been a casual kind of friendship lunch for him.

"Oh, no. I know. I... I probably should've said something."

"Oh, no. Seriously. It's fine. I mean that's not... That's great for you, though."

Chapter 20 by Azlin

"Yeah. He, uh, he actually works at Dunder Mifflin, too."

"Whoa, hold on. Pam are you engaged to Dwight?"

"No!" She laughed, relieved to be back to joking.

"Well, it's not Michael, is it? Because that would just be wrong, Pam."

She kept giggling as he listed everyone from Kevin to Creed. Then she interrupted.

"Actually his name's Roy. He works in the warehouse."

"Oh, right, good. You know you had me worried there." He chuckled.

"Yeah, I'd be worried too." She shook her head, imagining being engaged to Creed. And then, without thinking, she imagined being engaged to Jim.

Chapter 21 by Azlin

"Anyway, he's been, um, saving up for the ring, so I think we're gonna go pick one out next month."

"Right." He paused, and she glanced at his face for the first time since mentioning Roy. His expression was inscrutable. "Well, that sounds great, Pam. Congratulations." The word seemed a little hollow coming from him, but she was sure she was just imagining things.

"Thanks. And, uh, I'm sorry... that I didn't, um, tell you."

"Oh, no. Seriously. Don't apologize. It's totally fine. I'm totally fine."

"Okay."

"Okay." He really did smile genuinely then.

Maybe this would still work out.

Chapter 22 by Azlin

What if I hadn't been so afraid to mention that lunch to Roy?

What if I hadn't told Jim about my engagement at all that day? What if instead I had told him about the fight Roy and I had the week before? Would we have figured out then how much better the two of us could be together?

What if I never get another chance to tell him how glad I am that he asked me to eat lunch with him?

What if Jim never looks at me that way again? What if I never even see him again?

Chapter 23 by Azlin
Author's Notes:

Bonus chapters today? I am just too nice to you guys! ;)

Dedicated to grilledcheese for waving at the 'Hood, and to TooLateKev for knowing everything.

 

Months passed. Pam still thought of Jim as a friend. Sometimes she even thought he was her best friend. Except for Roy, obviously.

But she had stopped comparing Jim and Roy because there was just no point. They were too different. She couldn't change either one, so she kept thinking she was lucky to be able to enjoy them both nearly every day.

As for her crush... it was... there. Less intense than on his first few days, but still stronger than she wanted to admit.

But they were friends. It was natural that she'd have some feelings for him.

 

End Notes:
Thanks so much to everyone who's reviewed and expressed interest in this story! I really appreciate it!
Chapter 24 by Azlin

She couldn't figure out if Jim had any kind of feelings for her. Sometimes she thought he did. She'd glance up to find him looking at her; he'd grin sheepishly and go back to work. It was kind of cute, actually.

But there were other times when she felt like just a buddy to him, a partner in his pranking crimes, someone to pass the day with. But nothing more than that.

When Roy had first started liking her, it had been obvious. Unbelievable to her, but obvious to everyone in their high school.

With Jim she just didn't know.

Chapter 25 by Azlin

She knew it shouldn't matter to her whether Jim liked her or not. She was engaged, so there was no way anything could happen. But that didn't mean she didn't think about it every now and then.

Eventually there came a day when she knew she'd have to give up thinking about it, or she would make herself crazy. Whether or not she liked him, or he liked her. None of it made any difference really.

For her own sake it was better to stop thinking and let things just be.

But ignoring it only seemed to make it worse.

Chapter 26 by Azlin

It was ten o'clock on a Tuesday morning and she had just returned from the kitchen, yogurt cup in hand. She dug her spoon out of the middle drawer where she always kept it, not trusting the community silverware in the kitchen. As she was pulling the foil lid off the cup she felt that familiar tingle that meant he was leaning over her from the other side of the desk.

"Hi."

"What's up?"

"Okay, look, this might sound weird, and there's no reason for me to know this, but that mixed berry yogurt you're about to eat has expired."

Chapter 27 by Azlin

Her face felt frozen in a weird half smile, so she shook her head a little before responding.

"Oh. Um, thanks."

He was grinning that sheepish grin again, and she had to stand up and grab the yogurt so she could go throw it away in the kitchen garbage.

She leaned against the kitchen counter a minute later, still unsure about what had just happened. But something had definitely happened. And she couldn't keep ignoring it anymore.

Maybe that innocent, little crush that she had on Jim wasn't as little as she had thought. And it certainly wasn't as innocent.

Chapter 28 by Azlin

 

What if he had followed me into the kitchen? What if I had said something to him that day?

What if I'd at least tried to acknowledge what was going on even just to myself instead of just shoving it to the back of my mind out of fear, or bewilderment, or even just habit? Why in the world did I let it become a habit to avoid dealing with all those feelings?

Didn't I know better than that?

Why didn't he push me to talk about it sooner? What if he'd known that I wanted to talk about it?

 

End Notes:
That's the last of them for today. Thanks again for reading!
Chapter 29 by Azlin
Author's Notes:
It's my one year fic-iversary! So I'm celebrating by posting these tonight instead of tomorrow even though I'm only posting four right now. Enjoy!

 

It wasn't just the yogurt, of course. She lay in bed that night (alone, because she and Roy were fighting again), trying to add up all the little things that had led to her epiphany earlier that day. She'd begun calling it that sometime after lunch, after failing to come up with a reason not to.

Because it had been a realization. Somehow at that moment she had just known. And now she wasn't sure if it was the realization itself or the unmistakable, undeniable clarity of it that scared her most.

She liked him. She really... really... liked him.

 

Chapter 30 by Azlin

It really wasn't just the yogurt. It was the fact hat he'd been looking out for her. He always did. And the way he'd said it, like he was afraid to acknowledge that he knew so much about her habits, about her. Like he couldn't admit he thought about her. Even though she knew he did.

And there were other things. The way his eyes lit up when they schemed together. He was always so happy. Patient, but not patronizing.

He just understood her, in a way that no one ever had. A way that Roy never came close to.

Chapter 31 by Azlin

Pam tossed, giving up on sleep again. Brutal honesty was the only way to move past this.

So she liked Jim; that didn't change anything.

She had been with Roy for years; whereas she'd known Jim for seven months.

And Roy was there for her. Sure they fought, everyone did. But...  Besides, everyone knew Roy could do so much better than her.

She had made a promise to Roy. She was marrying Roy.

And liking Jim wasn't part of the marrying-Roy plan. Either the plan would have to change, or liking Jim would.

Pam sucked at changing her plans.

Chapter 32 by Azlin

 

What if I had known then that he liked me too? What if I had paid more attention, instead of just dismissing the thought all the time?

What if that fight with Roy had stuck?

What if I had told Jim that I wasn't always so sure about marrying Roy? How much of that did he know without me telling him? Why didn't he say something sooner?

Why has it always taken me so long to deal with this? Why am I so slow? And didn't he know that it would take me a long time to process all this?

 

End Notes:
Thanks to everyone who's reviewed! I really appreciate your feedback.
Chapter 33 by Azlin
Author's Notes:
Sorry about the delay. Darn that real life! Always getting in the way of the important things like fanfic.

 

A couple of months later things had gotten even worse between Pam and Roy. She wasn't happy, and she knew it, but she also knew that no relationship was perfect, and she wasn't willing to give up on Roy yet.

But they fought almost constantly. Usually over little things, and often about money. He'd spend too much at the grocery store, or she'd buy the wrong kind of toothpaste.

She'd snap at him. he'd yell at her. And then they'd spend the rest of the evening in opposite ends of the apartment.

She hated that her life was like this.

 

Chapter 34 by Azlin

There were good times, too, though. Like when they'd tried to make Roy's grandma's cookies. They'd accidentally added too much salt and had needed to triple the recipe. They'd laughed a lot that night and brought cookies to everyone at work the next day.

Roy could be really sweet sometimes. Which only made it harder when he wasn't. Pam often thought of Roy as two different people; she just wanted to know which one would wake up beside her in the morning.

As for Jim, he was dating someone. Pam was trying really hard not to let it bother her.

Chapter 35 by Azlin
Author's Notes:
I bumped the rating up for some mild language in this and the next chapter. I thought I'd note that here just in case someone's super sensitive about that.

 

By October, the good times were mostly a memory. For the first time in her life, Pam was actually excited to go to work, but only because it was the one place she could escape from the constant bickering.

"You just don't get it, do you? I mean, has it ever occurred to you to think about what I want?" she knew her voice sounded shrill, but she was past caring.

"Oh, come on, Pam! Don't start this. I am so sick of you and your damn speech."

"What speech?"

 

Chapter 36 by Azlin

"You know the speech." Roy's voice changed to a whiny, girlish pitch. "Roy! You never listen to me! I do everything and you just sit there on your lazy ass!"

"Whatever, Roy."

"No, you know what? If you're so sick of me, then why you don't you just go?"

"Fine!"

Without thinking, Pam spun around and marched down the hallway, pausing only to grab her coat. Roy followed, not saying anything until she reached the door.

"What're you doin', babe?"

"I'm leaving." She just looked at him for a second, then turned and walked out, slamming the door behind her.

Chapter 37 by Azlin

Roy caught the door.

"You're not leaving. You're wearing pajamas."

"I don't care," she shouted defiantly.

"Pam, would you stop?"

She didn't answer, just continued walking, Roy following her.

"Where're you gonna go, huh? You don't have keys; you can't take the truck. Where're you goin', Pammy?" There was a faint note of contrition in Roy's taunts; she chose to ignore it.

Fingering the phone in her pocket, she tried to think of someone to call. Her parents were hours away. She hadn't talked to her high school friends in months.

That left work. And work meant just one person.

Chapter 38 by Azlin

Pam glanced back. Roy was still following her. His pace had slowed in the chilly autumn night, but he was there, half a block back.

She stared at the phone in her hand, her own pace slacking. It was late. Sometime around one, she thought, but Jim's name on her phone screen was already consoling her. She knew he'd come instantly if she called. He'd take her away from all this. He'd make her laugh, then pull his arms around her tightly and let her cry. It wouldn't matter what he was doing, or who he was with. He'd come.

Chapter 39 by Azlin

And still she hesitated. She couldn't come crawling to him like this. Couldn't be that desperate. Not with Julie around. She knew there was nothing serious between them, but Pam couldn't help feeling annoyed at Julie. After all, Jim was... Julie wasn't his type. She didn't want Jim getting hurt.

"What're you doin'?" Roy asked, now only steps behind her.

Her finger was still on the call button. It would be so easy.

"Come on, babe. It's cold. I'm sorry, okay? Let's go home, talk about this tomorrow."
She couldn't respond. She felt frozen. Like being trapped in a nightmare.

Chapter 40 by Azlin

 

What if I hadn't been so fed up with the situation? Would I still have needed him so badly if Roy hadn't been... Roy? Would we still have become as close as we did?

Why couldn't I see that there was a reason he was always there for me? I should have known we were more than best friends. Why didn't I realize how hard it was for him to keep supporting me through everything?

What if I'd tried to get him to tell me sooner? Would he have done it then?

 

End Notes:
That's all for now! Hope you're still enjoying these!
This story archived at http://mtt.just-once.net/fanfiction/viewstory.php?sid=3301