AUTHOR NOTE: I'll try and make this quick. It's been so long since I've written about this beautiful couple. I miss writing so much and figured a good way to get back into it would be by writing fanfiction again.

That being said-here's what you need to know about this fic. A lot of it will be AU but I still tried to keep some parts like the show and some parts like what could've actually happened. What started out as a "5 Times" fic, turned into a much rather long piece, that's why it's most definitely a chapter story.

Setting: This takes place after Michael asks Jan to go to Jamaica with him.

Oh and please let me know what you thought! Makes my day!

It's Friday night, the day before Christmas Eve. Jan is still at work because they're having their annual Christmas party. However, she isn't necessarily "partying". She was trying to finish some work before leaving for her vacation. She's more than happy she was in her office otherwise she would've missed Michael's phone call.

Now, Jan sits in silence trying to process what just happened. She's still surprised at how easy it was to say yes. There was no hesitation and no fear of losing her job. Okay well yes, she is a little worried what they'll say but she'll be sure to read over the contract very carefully...just to make sure this isn't too risky.

Michael inviting her was the perfect sign she was looking for. She just had a session with her psychiatrist the day before. And as always, the subject of Michael came up. She, since probably Chili's, has been fighting these so-called feelings towards Michael. She couldn't bring herself to admit that she was attracted to him. She sorta hoped these feelings were just that. Feelings. Something that would eventually go away. Something that was just a crush. She was wrong…she was dead wrong. Because she just said yes...because he just invited her. She instantly started daydreaming about them in Jamaica and fantasizing about things they're gonna do. Well…hopefully do. She tries holding back a smile-afraid someone would see her.

Jan is actually supposed to be going to Scottsdale to visit her sister. She's more nervous canceling her trip to her sisters' last minute than she is taking this impromptu trip with Michael. She takes a deep breath while shaking those thoughts out of her head. She knows her sister will understand.

"Hey Julie. Do you have a minute?"

"Hey Janet-what's up?"

Jan takes a deep breath, "I'm so sorry to do this, but something came up."

"Oh no! You're canceling? The day before you leave? Jan! Peyton is gonna be so crushed."

"I know. I know but something huge happened and I hope you understand why I have to do this."

"What's going on?"

"He invited me to Jamaica with him, Julie." The tone in her voice told her sister that she was indeed grinning. Yet, not hearing a word in response makes Jan continue, "I mean…I have to do this, right Jules? I've been waiting for some sign telling me to jump and this is as clear as it can get. Of course it had to happen now. I'm so sorry. Please tell Peyton that I'll come down in a month or two. I promise. I just…"

"It's okay, Jan. Calm down. You're right, you have to do this. You deserve to be happy, you know? Especially since Richard was such an asshole."

"Thank you so much for understanding. You have no idea how nervous I was to tell you."

"So how in the world did this happen? I mean, taking a trip together to a romantic place when you aren't even together? Isn't it crazy? Even for you?"

"Well, yes and no. I mean we kind of have a history and there's definitely a different kind of tension between us. I mean-I don't know-it's kind of a huge risk since my job is at stake. If anyone finds-"

"Wait. What? Why is your…do you work with this man? Oh my god, he's your boss! This is why you've never really said where he worked. Jan! You have to be careful!"

"Oh my god, Julie! He is most certainly not my boss, okay?" Jan takes a deep breath as her sister waits for her to continue. "I'm his boss."

"Oh my god…that's worse." All Julie can do is laugh.

"Yeah, you're probably right. Well listen-again, I am so sorry...I will be sure to make it up to you and Peyton."

"Have fun, Jan. Oh! And I want to know all the details. Well...almost all."

Michael is reclining back in his office chair...hands behind his head...feet up on his desk...grinning from ear to ear...not caring who notices.

Michael just asked his boss to join him in Jamaica! And she said yes. Without hesitation even. In fact, he hardly was able to finish his question before she figures he should probably play it safe, though, and not expect anything (i.e. sex) since Jan said once that nothing will ever happen between them. He's sure that she only desperately agreed because she needs to get away. She would've said yes to anyone. However, this could be his chance to prove to her that he's not all that bad.

Michael knew he always had a thing for Jan. That whole 'will they...won't they', 'on again...off again' relationship. He thought of them as the Ross and Rachel couple of the office. No one else would ever view them as that couple because well, Ross and Rachel actually had a relationship and actually had sex. This is all irrelevant anyways because he already decided to play it safe and not expect sex. A real friendship would be amazing. Friends with benefits. He giggles as he shakes his head and picks up the phone again.

"Michael?"

"Mi madre! Que pasa?"

"Do you have any idea what time it is?"

"Oh I'm sorry! I forgot-you old people like to go to bed at 6:30"

"For the hundredth time, I don't go to bed at 6:30. Michael, dear, what's going on anyway?"

"I did it Mom! I finally did it! And she said yes…finally! She finally said yes-can you believe it?"

"I'm not following…"

"We're going to Jamaica. The most beautiful place on this planet. And I'm going with her."

"Don't you think it's a little soon, Michael? How long have you even been together?"

"Well, I guess we're kind of not together. I don't know…it's complicated."

"You're not talking about that Carol you were dating?"

"Oh! Yeah…no. That ended like ages ago. Or, well like 8 hours ago."

"Oh my god, this is a lot of information to process at 11:00 at night."

"I invited Jan!"

"You what? Oh my god, Michael! You have to be careful. She is your boss. If and when this-thing-ends, life around the office is gonna suck. Seeing each other is going to suck. And when-"

"It's okay Mom! It's not going to end because nothing is going to start. We're just going together as-as friends."

"Yeah, right. Like that's your only intention?"

"Scouts honor."

"Okay well have fun and I-uh-let me know how it goes. Love you Mikey. Oh and don't call me this late again…unless it's a life or death emergency."