Six Times Pam Gets Proposed To and One Time She Proposes by nicemorningtoo
Summary:

Six different proposals, one actual wedding that ends in a proposal of her own. 

Written for secret santa! 


Categories: Jim and Pam, Present, Past, Episode Related Characters: Jim/Pam
Genres: Childhood, Fluff
Warnings: None
Challenges: None
Series: Secret Santa Fic Exchange 2020
Chapters: 7 Completed: Yes Word count: 3760 Read: 5118 Published: December 21, 2020 Updated: December 21, 2020

1. Mason by nicemorningtoo

2. Jackson by nicemorningtoo

3. Kameron by nicemorningtoo

4. Roy by nicemorningtoo

5. Roy Part 2 by nicemorningtoo

6. Jim by nicemorningtoo

7. Pam by nicemorningtoo

Mason by nicemorningtoo
Author's Notes:
This was so much fun to write. I promise it gets very Jammy at the end lol. I think I used all 7 prompts, but some are used more obviously than others. I hope you all like it!

One.

 

Her parents have the same handful of stories that seem to go into rotation every holiday season.  They had their funny ones like how Pam broke her leg in first grade from throwing a tantrum and how she immediately told Penny that Santa wasn’t real even though she was specifically told not to do that. They also had their proud parent stories like winning two art contests in middle school and graduating at the top of her class. But out of all of these favorite stories, there’s one story that Pam knows everyone in her family has memorized; the time she got married in kindergarten.

She’s heard the story enough to have every detail memorized, but she can actually only remember little bits and pieces. She remembers his name was Mason. He was just a tiny bit shorter than she was, with brown hair and freckles. They would sit together during lunch and look at books together during recess. She remembers that he eventually started giving her little gifts and notes, but she wouldn’t have remembered what they were if her mom hadn’t kept some of them. A tracing of his hand, a hair tie, some notes with letters that she knows are supposed to be words, but she has no idea what they are supposed to say, a hot glue gun refill, the homemade box that he had given her for valentine’s day that was filled with chocolates and a small teddy bear, and, her parents’ favorite, the gumball machine ring he had given to her for her birthday. They also kept the note that went along with the (now broken) ring that reads “hapee birday. will yu maree me?” with a heart drawn underneath.

She remembers wearing a white dress to school one day and Mason had on a black polo. She remembers her best friend, Danielle, telling them to say, “I love you” and then kiss. She can still hear the giggles and little “ew”s from the few classmates that had joined the audience. Their honeymoon was spent under the slide where they kissed one more time before going off in separate directions to meet up with friends. She wore that gumball machine ring until it broke the summer after kindergarten, right before they moved, and she never saw her five-year-old husband again. Sometimes she wonders if his parents tell the story as much as hers do.

Jackson by nicemorningtoo

Two.

 

Pam considered herself pretty lucky when it came to bullies in school. For someone who was quiet, plain, into art, and a little nerdy, she only got the occasional snide comment or rude remark. Most people just left her alone, though, which she appreciated more often than not. She had a few close friends, all of them from her art classes, all of them flying under the radar.

Which is why she knew something was up when Jackson, top pitcher of the seventh grade baseball team and a guy she had never spoken a word to, came up to her one day after math and asked her out. If she hadn’t seen his friends trying not to laugh a few steps behind him, she might have said yes. Instead, she closes her locker and walks around him with a polite but quick, “Thanks, but no thanks.”

He grabs her elbow and turns her around before she can get too far, “C’mon. I think we could really work out.”

She raises an eyebrow and removes her arm from his grip, “Really, no, I’m good.”

“I’m serious! Watch!” Her eyes widen in horror as he gets down on one knee, she can hear his friends now cracking up behind her and she can feel everyone’s eyes on them as they walk past them to their classes. “Pat, will you please marry me?”

Her cheeks are burning and she quickly turns to head towards English, ignoring Jackson completely and trying to block out the whistles and “boo”s coming from around her. It doesn’t even register until she’s sitting at her desk that he hadn’t even gotten her name right.

Kameron by nicemorningtoo

Three.

 

She’s two months into her sophomore year of college when her and Roy break up for the first time since getting together junior year of high school. She wanted to get married and he didn’t, “at least not right now, Pammy,” she wanted to get a degree in art and he thought a degree in science made way more sense, she prioritized studying and her on-campus job and he thought she spent too much time at school, ignoring him. Overall, she had realized they weren’t on the same page anymore and decided they needed a break.

Having not been in the dating game for the past four years, it takes her a little while to get back into it. It’s Isabel who finally convinces her to give Kameron, the cute guy who sits in front of her in Economics, her phone number. After a couple of phone calls and one study session, he asks her out on an official date. They go out to see a movie and grab some pizza afterwards and she had fun. It reminded her of her and Roy’s first few dates, relaxed and casual. She agreed to a second date, going to the Everhart museum downtown. He listened carefully as she explained the different art styles and waited patiently as she read the plaques next to her favorite pieces. He ended the date with a kiss on her cheek outside of her dorm room and a promise to call her tomorrow.

Their third date was the following weekend. Kameron had decided that the third date was when he would bring his A-game, taking her to a nice steak restaurant just outside of Scranton. She had assumed it was to impress her, to gain access to what the third date usually means, but he apparently had something else in mind.

She had just taken a bite of her salad when he reached over and took her hand into his. She smiles at him and squeezes his hand gently, causing the grin on his face to grow just a little bigger, “Pam.”

She keeps her smile, but she can tell by the tone of his voice that he’s about to say something serious, and she’d be lying if she said that it didn’t make her a little nervous. She liked the guy, could see herself going out with him for a while, but if he was about to say the L-word, she wasn’t quite there yet. “Kameron.”

“Listen, this might be crazy… but I feel like we have a special connection. Even though we have only been dating a couple of weeks, I feel like we’ve known each other for forever.” She watches in horror as he stands up, only to bend down on one knee. She glances around when she hears a couple small gasps, over half of the restaurant looking at them. She suddenly feels thirteen again, surrounded by classmates as Jackson looks up at her, his friends laughing, and she feels humiliated. Only this time, it’s worse. Where she knew Jackson was trying to joke around, completing some stupid dare, Kameron wasn’t joking. When Kameron asks, “Will you marry me?” he has an actual ring in between his fingers and such a genuine look on his face. She tries to whisper, tries to be as discreet as possible as she rejects his offer, but he just looks at her confused, as if she was speaking another language. She quickly stands up, quietly thanking him for dinner and telling him that she will call a friend to pick her up.

She doesn’t look back as she walks out the front door, dialing Isabel’s number. She also makes a mental note to ask her advisor to put her in a different Economics class.

Roy by nicemorningtoo

Four.

 

Three months after graduating, she had run into Roy at Target. She asked about his family while he asked about hers, and by the time she headed to the checkout, she had agreed to meet up for drinks on Friday. She truly only expected to catch up, but then he asked her out again and she agreed and before she knew it, he had asked her to be his girlfriend again. He promised to be more committed and supportive, and she was always a believer of second chances, so she says yes.

He gets her a job as a receptionist at Dunder Mifflin, promising that she can quit whenever she finds something that she likes better. She quickly finds out that her boss is insane and her coworkers are strange, but her paycheck is decent and the job is easy, so she sticks it out, even when she finds other opportunities. Roy insists that she’d make more money if she stayed here (she wouldn’t), they save so much time and money by carpooling (not that much, really), and that he loves working in the same building as her (she wants to believe this is true, so this is really what makes her stay).

She’s a little shocked when she unwraps the small velvet box on Christmas morning, opening it up to reveal the simple diamond ring. Roy gently takes it out of her hand before getting down on one knee and grinning up at her. She tells herself that she’s just taken aback by how soon he has proposed, that’s why she doesn’t feel as excited as she thought she would. She loves Roy, truly, really loves him. She says yes and he slips the ring onto her left hand before pulling her in for a kiss.

Her back is to Roy’s chest, his arm around her waist as he snores behind her. She looks down at her ring for what feels like the millionth time since this morning. Her sister had quietly called it plain during dinner at her parents’ house, and although she knew there was nothing striking about the ring, Pam actually really liked it. She felt like it suited her, and she was happy. Happy to be engaged, happy that Roy was now her fiancé, happy that she could actually start planning a wedding.

But, as she looks out her bedroom window, the snow outside piling on higher as the night goes on, she can’t shake the little nagging at her heart. She loves Roy, so why does she feel like something is missing?

Roy Part 2 by nicemorningtoo

Five.

 

“I’m cold.” She gives Jim a small smile before walking around him, heading back into the heated cabin of the boat.

She stops in the doorway, though, watching as Roy takes another snorkel shot. She looks back and sees Jim is looking down, elbows resting on the ship’s railing. Taking one more quick glance inside, she decides that even though she really is cold, she’s not ready to deal with… whatever is happening in there.

She closes the door quietly, keeping Jim in her periphery, making sure he doesn’t see her walk around the cabin towards the front of the ship. She’s surprised to find Dwight, humming to himself and holding onto a wheel she’s pretty sure is only there for kids to pretend with. She glances up and her thoughts are confirmed when she sees the helmsman watching from above, actually steering the boat. Jim would love this, she thinks as she walks over to Dwight.

She leans back against the railing, facing him. “Hey, Dwight.”

He looks at her for a second before focusing on the water in front of him. “Pam.”

She glances at the city lights before looking back at him, “What are you doing?”

He sighs, “What does it look like I’m doing? I’m making sure we don’t capsize.”

“Seems like you’re doing a good job, then.”

“Obviously. What are you doing out here?”

She shrugs, “I needed some air.”

“You know there’s a back of the ship, too, right? So, you don’t have to distract me from my job?”

“Yeah, but…” she glances towards the back of the boat even though she can’t actually see it. She sighs, “Jim’s there.”

Dwight scoffs, turning the wheel ever so slightly to the right. “Aren’t you two best friends?”

“Yeah, but… I don’t know. I was talking to him about Roy and he just got kind of quiet. Like he doesn’t want to get caught between us, but I don’t get it. I just need to vent sometimes; I’m not asking for him to take sides.”

“Jim’s an idiot, he couldn’t give you good advice anyway.”

“That’s not—”

Dwight continues, not letting her finish, “Let me give you some advice. You should listen to Roy, he’s your fiancé, not Jim. Women should always listen to their male counterparts, especially if they are engaged.”

She raises an eyebrow, “What if my male counterpart won’t listen to me?”

Dwight shrugs, “That’s not his job. His job is to provide for you.”

“He has to do more than just provide for me if I’m going to spend the rest of my life with him.”

“If you believe that, then why are you bothering to marry him if he isn’t what you want?”

“I didn’t say that. I’m marrying him because I love him.”

“Is that enough for you?”

“Yes. I think so.”

He shrugs, as if the answer is simple, “Then marry him.”

She nods, and now she’s freezing instead of just cold, so she gestures towards the cabin. “I’m going inside. Do you need anything?”

“No, I’ll be in soon, once I make sure our path is clear.”

She looks out at the empty lake, unsure of what exactly could count as an obstacle against a ship of this size, but she’s not going to fight him on this. She pushes herself off the railing, “Well, thanks, Dwight.”

“I don’t need your thanks.”

“I know. But I’m saying it anyway.”

She could have sworn she heard a mumbled “you’re welcome” as she walked past him, but maybe it was just the cold getting to her. She goes in through the side door, not wanting to risk the back in case Jim is still there. She spots him at the bar, though, talking to Michael and Captain Jack. She just sat down with Katy when Dwight comes in, joining the other two at the bar.

She rests her hands on the table as Katy greets her and Pam returns her smile.

Katy gestures towards Pam’s left hand, “I’d like to be engaged. How did you manage to pull that off?”

She immediately starts fidgeting with her ring, a nervous habit she has formed over the past few years. “Uh, I’ve been engaged for three years, and there’s no end in sight. So… you don’t wanna ask my advice.”

“Well, Roy seems like a great guy.”

She nods, “He is.”

Katy nudges her arm, “He’s cute, too. You’ve got good taste.”

She laughs a little and thanks her before changing the subject, asking Katy more about her purses.

Katy is in the middle of telling her about her latest addition, a Michael Kors leather handbag that she thinks Pam would love, when Jim is suddenly beside her, asking her if they can talk. She’s not able to respond before Roy is at the microphone and asking her to marry him on June tenth and it’s suddenly all real. She’s getting married and they have a date and tears sting her eyes as she walks up and kisses Roy. Snorkel shots, artsy fartsy comments, any doubts from tonight vanished when her lips met his and she knew that this was finally happening.

She mistakes Jim's fake smile as genuine, missing the flash of devastation that had crossed over his face.  

Jim by nicemorningtoo

Six.

 

When she was little, she expected some huge proposal. Maybe at a fancy restaurant, where her ring would be hiding at the bottom of her glass. Maybe during a dream vacation, her would-be fiancé down on one knee in front of the ocean or on top of a mountain. She pictures getting engaged a hundred different ways. In front of her parents. In a museum, surrounded by art. A banner pulled by an airplane. At a concert of her favorite band. Privately at home, like how Roy had done.

She never expected the man of her dreams to be down on one knee during a break from work, in front of a gas station, in the pouring rain.

But, she quickly found out, she couldn’t have asked for anything more. She suddenly didn’t care about fireworks or fancy dinners or some made up resort her preteen brain had made up. Because Jim was there, and he said he couldn’t wait any longer and he asked her to marry him and she said yes.

She was a little upset that he had to go back to Scranton, but he had promised to drive back up as soon as he got off. So, now she’s sitting in her dorm room, eagerly waiting for the knock on her door that announces his arrival. She’s about to text him for the eighteenth time since she got back to school when he knocks. She jumps out of bed, throwing the door open and kissing him before he could greet her.

He doesn’t seem to mind, though, as he leads her back into the room, closing the door behind them. She pulls back, cupping his face and looks up at him. She couldn’t wipe the stupid grin off her face even if she wanted to. “We’re getting married.”

He nods, his grin just as big as hers, “We are.”

She pecks his lips before wrapping her arms around his waist, resting her chin against his chest. “I love you.”

He kisses her forehead, his hands resting on her arms, just below her shoulders. “I love you, too.”

She buries her face in his chest, mumbling, “We’re getting married.”

He chuckles, “You already said that.”

“I know. I just can’t believe it.”

His fingers lift her chin so he can look at her. His eyes are full of disbelief and adoration and just pure love. His voice is soft, and she knows everything he’s thinking when he says, “Me neither.”

 

She pours hot water into two mismatched mugs, the water turning a light brown as the tea slowly dissolves. She doesn’t use the teal teapot very often, usually keeping it on the counter as a daily reminder of what she now has. She uses it for special occasions, though, like today. She hands Jim his mug before crawling back into bed, practically sitting in Jim’s lap so they can both fit on the single bed. He wraps his free hand around her waist, slipping it under his t-shirt that she had changed into so his thumb can rub tiny circles against her skin. She leans into him as she sips from her mug, the warmth of the tea incomparable to the warmth she has felt since Jim got down on one knee. Really, since he asked her out to dinner for the first time.

He kisses the top of her head and then says, “I have a very important question for you.”

She chuckles, “You already asked me an important question today.”

“This one is wayyyy more important.”

She looks up at him with an eyebrow raised, “What?”

He tries to look serious, but she can see the corners of his lips fighting a smile, “Am I going to have to stop calling you Beesly?”

He gives into his grin when she laughs and leans up to kiss him softly. She pulls back just enough to say, “No, you don’t.”

“Good. I don’t think I’d be able to even if you wanted me to.”

“You’re crazy.”

“For you.”

She rolls her eyes, but she grabs his mug out of his hand and sets both cups onto the table next to her bed before she turns back to him. She wraps her arms around his neck, tangling her fingers into his hair as she kisses him, lying back and pulling him on top of her.

Pam by nicemorningtoo

Seven.

 

After dealing with her parents all day, her veil tearing, running away with Jim to get married on a boat, getting married again in the church, an insane reception that Michael almost ruined twice, all while five months pregnant, Pam is exhausted.

She’s snuggled up to Jim, her head on his bare chest and his arm wrapped around her bare waist, his hand resting on her bump that is now starting to really show. She traces small circles on his stomach as his breathing gets slower and deeper. She looks up at him when she thinks he’s asleep, his hair mussed and just the faintest hint of a smile on his lips.

She ghosts her lips over his chest and whispers, “I want to marry you.”

She looks up at him surprised when she feels the vibration of his chuckle against her lips. His voice is soft and thick with sleep, “You already did. Twice.”

She leans up so she can pepper kisses down his jaw, “But I want to marry you again.”

He opens his eyes and looks down at her, “Even with all of our coworkers dancing to “Forever” down the aisle?”

She laughs, “I liked our boat wedding way better.” She places a hand on his cheek and kisses him gently, “But I’d put up with anything as long as you’re on the other side.”

He hums, “And you say I’m cheesy.” He kisses her forehead, “I’d marry you as many times as you’d let me.”

She slides her hand down and around his waist, pulling him towards her, “Do you think Puerto Rico has a place we can elope?”

He pulls her flush against him as she wraps a leg around one of his, “What, like their own Vegas?”

“Yeah.”

He runs a hand over her bump and shrugs, “Maybe,” he looks at her and grins, “but I can’t get eloped without an Elvis impersonator.”

She places her hand over his on her stomach, intertwining their fingers, “Obviously.”

He rolls her over so she’s on her back and he’s above her. “I love you.”

As his lips meet hers and her fingers get lost in his hair, she thinks about the two rings on her left hand. Promises of a lifetime with the man in front of her, both of them ready to officially start their lives together. She sighs contentedly as he moves down her neck and she thinks, We’re married.

Finally.

End Notes:
Again, this was sooo much fun to write. Thank you WW and TPB for letting me steal names from them, and a huge thank you to TPB for the final chapter idea. I hope you all liked it! Merry Christmas!!
This story archived at http://mtt.just-once.net/fanfiction/viewstory.php?sid=5952