Looking around for her sister, Penny drummed her fingers on the reception desk as she bit her lip. She was late arriving for lunch and was worried it would mean Pam wouldn't have time to go out as planned, and she really needed the bathroom. Stupid slushie machine at the gas station, what was she, five?

"Hey, uh, can I help you?"

Penny turned around slightly as someone approached the desk from behind her. His clothes looked to be at least a size too big for him and his hair was a mess, but there was something charming about him. She figured he must work in the sales department.

"Oh, I'm supposed to be meeting my sister - Pam - here?" Penny looked around in case she'd somehow confused this office for another, despite the giant Dunder Mifflin sign she had passed outside the door. 

"She's just gone to the annexe," Jim said as he made his way to the fax machine behind the main reception desk. "You can take a seat if you want until she's back. Unless you're in a rush, I can let her know you're here?"

"Umm, actually," Penny dropped her voice slightly, "would I be able to use your bathroom?"

"Sure," Jim put his papers to the side so he could take her through, "follow me."

"Thank you. I got tempted by a Slurpee on my way here."

"Aah. I had the same issue with a Big Gulp last week."

"Slurpee is way better than Big Gulp, though," Penny said. 

"True," Jim nodded as he held the kitchen door open. "Here you go, it's just there on the right."

"Thank you so much, umm-"

"Jim."

"Jim. Oh you're Jim! I've heard a lot about you," Penny grinned. 

"Oh?"

"Yeah. I'm Penny, by the way," Penny's eyes sparkled as she looked Jim up and down before turning and heading into the bathroom. 

A little bemused and a lot intrigued, Jim stared at the door for a moment before heading back to reception to send his fax and returned to his desk. Pam's sister had the same sparkle in her eye when she was amused as Pam did, so he had no clue what kind of things Pam had told her to induce that reaction. Maybe she liked pranks too? He liked that Pam talked about him though; when he'd discovered through poorly-whispered words that Pam's mom knew about him and wanted to know which one he was, he'd barely contained his grin. 

Penny returned a few minutes later, looking around to check if her sister was back. She gave awkward smiles to the few staff who paid attention to the stranger walking through their office, before deciding to take a seat at the empty desk in Jim's desk clump and scooting closer to him. 

Jim was just glad that Dwight was out on a sales call so he wouldn't have to explain his weirdness to Pam's sister. 

"So, did you really put someone's stapler in Jell-O?" Penny asked. 

"Oh, umm, yep," Jim nodded proudly. 

"I love it," Penny grinned. "And you made everyone in this office call someone by the wrong name?"

"Yes," Jim grinned slightly, putting his pen down. "Best money I ever spent."  

Penny then decided it was Jim's lopsided smile that was charming. She could see why Pam had a crush on him. "How do you come up with all of these pranks?" 

"They just come to me. It makes the day a little more interesting," Jim shrugged. 

"True, they can make the workday a little more fun. Though I'm still on my probation so I'm just... playing things safe."

"What do you do for work?"

"Pam didn't tell you? I'm a stripper at The Lucky Cat in New York."

"Oh! That's, umm, cool," Jim managed to say, completely taken aback. He could see Phyllis turn her head and Stanley raise his brows over at the next desk clump. 

"Kidding! Ha," Penny grinned. "I just started at a PR firm."

"That's a shame, she has the body for a stripper," Phyllis mumbled to Stanley. 

Having overheard the comment, Jim widened his eyes at Penny in amusement. Penny was less subtle, instead turning toward Phyllis and whispering, "thanks, but I get really bad stage fright, so it's not really for me."

"I'm sorry, I didn't mean-"

"It's okay," Penny chuckled, turning back to Jim and pulling a face. 

"Yikes," Jim raised his brows and cleared his throat. "So, PR? That sounds kinda cool."

"Yeah, I mean it's just a really small company in Philly but I'd love to move to New York or any big one where I could travel to different events and stuff."

"That does sound cool." 

"I can't believe Pam hasn't told you like anything about me. Like, soon as you said you're Jim I was like okay - sales, plays basketball, only has ham and cheese or tuna sandwiches for lunch, so many pranks." 

Jim blushed, though he couldn't deny he was elated that Pam spoke about him to her family - and these facts were solid proof that she spoke about him in some detail. "I mean, uh, I guess talking about her sister in PR is a too interesting topic for this office."

"Mm, maybe," Penny nodded as she looked around.

"She had mentioned that you were looking for a job a while ago," Jim offered. 

"Yeah... well, I didn't fancy staying in Scranton. Though that seems to have worked out a bit for Pam," Penny smiled conspirationally. 

"Oh. I - in what way?"

Jim never received his answer, as in that moment Pam entered the main bullpen with her blue notebook clutched firmly in her right hand, as if all the meetings she had just written in might slip out if she didn't hold onto it for dear life. Her eyes widened when she saw her sister sitting comfortably in Dwight's chair at the side of Jim's desk, comfortably chatting away. A mix of anxiety, jealousy and dread washed over her and she felt her cheeks flush. This couldn't be good; Penny knew way too much and was not a subtle person. 

"Penny!" Pam called a bit too enthusiastically, though the panic was still evident in her voice. 

"Hey, Pam!" Penny spun around in the chair. "Sorry I was kinda late, but Jim has kept me entertained while you were busy."

"Yeah, I had to go schedule these meetings with HR and Customer Service, sorry - I, uh, ready to go?"

"Sure!" Penny hopped up. 

"What have you guys been talking about?" Pam asked as she followed Penny and Jim over to reception, trying to sound casual. 

"Oh, she's told me all your deepest, darkest secrets," Jim grinned. It was adorable how flustered Pam was. 

"Oh yeah?" Pam rolled her eyes at him before heading around her desk. She knew he was joking, or he wouldn't have said anything, but she couldn't rule out Penny mentioning that she thought he was cute or something. 

"Oh yeah," Jim nodded.

"Guess I'll have to quiz you later," Pam said, putting her notebook away into her desk drawer and going to put her coat on. 

From the corner of his eye, Jim clocked that Penny had snuck back off to his desk and was scribbling something on his legal pad while Pam had her back turned. "Bring it on, Beesly."

"It was nice meeting you, Jim," Penny said, reappearing at his side before shaking his hand and joining Pam. 

"You too," Jim raised his hand in goodbye and threw Penny a smile. "Enjoy your lunch, Beesly sisters."

"Thanks!"

"See you later," Pam said, "I don't have any more meetings to join so just let Michael know I went on a late lunch when he's done with his conference call."

"Will do," Jim nodded. 

Once they had left, Jim returned to his desk and looked down at the note Penny had scribbled on his legal pad. 

Take your shot with her. 

Seriously.

In that moment, Jim looked behind him to where Pam and Penny Beesly had just walked out with a sad smile and thought, if only.

Of course, at the time he didn't know that Penny was often the one to hear Pam out when she was upset about Roy, questioning the relationship. Penny felt like Pam was constantly on the verge of breaking up with Roy but didn't have the confidence to follow it through, because it would mean changing everything she had known since she was in high school. Penny also knew that Pam had a thing for Jim - knew a little too much, actually, because Pam was a bit too chatty after a few drinks. 

Jim still had that very note when he moved to Stamford, and he almost tore it up because he'd shot his shot - seriously - and now he was in stupid Connecticut. And then he was back in Scranton and dating Karen and he both loved and hated that now he was the one in a relationship and Pam wasn't. 

Then during his first fight with Pam, shortly into their first week of dating when they finally talked - really talked - did Jim finally understand. Telling Pam "I'm in love with you" then running off when she didn't immediately give him the answer he wanted was not what a woman who'd been in a relationship for almost ten years needed. 

"You didn't give me any time to think, Jim, to process the whole thing. I needed you to be there for me when I made this huge life changing decision, and when you ran off it felt like I wasn't worth waiting for when things got serious," Pam had explained tearfully. She gestured wildly at the now severely crumpled note Penny had left all those years ago and said, "of course you had a shot - I just... needed to know that so I could make my next move!" 

A few weeks later over dinner in Penny's new studio apartment in New York City, Penny admonished him for being an idiot and thinking a full on declaration of love was taking his shot, but commended hm on finally taking another shot and asking Pam on a date. 

"Why did you never tell me to take my shot with Jim?" Pam asked.

"Because I knew you wouldn't," Penny shrugged. "I wanted to, but I didn't want to tell an engaged woman to cheat on her fiancé." 

"But it was okay to tell Jim to take a shot on an engaged woman?"

"I thought if Jim made it crystal clear that he was interested in you, you might finally have the confidence to break up with Roy and realize there are people out there who actually want you." 

"Oh."

"In retrospect, I wish I'd been writing a much longer note the whole time we were talking," Penny said to Jim. 

"Phyllis thought you'd given me your number," Jim chuckled. "I just went with it."

"Is that why she kept giving me sympathetic looks for like a week?!" Pam gasped.

"Possibly," Jim shrugged. "I said we're gonna go for Slurpees."