I'm suffering from insomnia due to my inability to stop coughing, so I wrote a story to pass the time. This is the story of Guybrush and Elaine's breakup between Monkey Island 1 and Monkey Island 2 as I see it.

Unbeta'd, so any mistakes are mine.

Every time you don't review, LeChuck punches Guybrush in the face. So REVIW PLZ.

"Elaine?" Guybrush called in a sinsong as he sauntered into the Governer's Mansion.

He had sort-of moved in with Elaine after the whole LeChuck debacle had come to a close, and she hadn't protested. They were in the throes of a fledgling romance, full of excitement and passion. However, when Guybrush returned home that day, he sensed something had changed. This was due in part to the large number of boxes filled with Elaine's things piled around the room.

"Plunder bunny? What's going on?" He shouted again, his cry echoing through the now-bare halls.

"Guybrush!" Elaine's breathless voice sounded from the top of the stairs.

"What's going on? Why the boxes?" He didn't want to admit that he thought he already knew.

"Guybrush... I-I'm leaving." She said flatly.

"Wha- why?"

Elaine forced her features to remain emotionless as she approached her now ex-lover. "Come on, Guybrush, you couldn't have thought this was going to last. I need to go work elsewhere for awhile, take care of some business on other islands under my jurisdiction." She turned to walk away, but not before turning and calling over her shoulder for good measure, "it's been fun!"

The young governer tried to keep the tears from flooding her eyes as she steadily walked up the steps back to her room, trying not to think about the shock on poor Guybrush's face as he stared after her. As she began to halfheartedly toss clothes into a suitcase, she pondered the necessity of their breakup. She knew that her dating a pirate could be a scandal, and could jepordize her position. People would question her ability to rule, and therefore, her laws. There could be chaos. She had worked too hard for her position to let some ludacris romantic fling tear it down. Plus, her family hated pirates! No, there was no way this whole Guybrush situation could be anything but trouble. But even as she told herself that over and over, she couldn't help but think she was making a mistake.

Just as she was considering going back down to at least talk to him again, she heard footsteps coming slowly - and what Guybrush probably thought was quietly - towards her bedroom door. Sure enough, she glanced up to find him leaning against the doorframe looking like a kicked puppy.

"Why are you leaving?"

"Go away."

"Did I do something wrong?"


"Is this because I set the kitchen on fire? Because I had no idea that grog was that flamab-"

"Get out!"

The force of her words was enough to stop him midsentence. So she plowed on.

"Look, Guybrush. I know that we've had a great time together, but it's time to move forward. You need to get on with being a pirate and I need to get on with being a politician. We're both young and at the beginning of our careers! We need to focus on our individual lives, not get lost in each other. And besides, what would people say about-"

"Is that what this is about!" Guybrush sputtered, ignoring the first part of her speech which they both knew was just filler. "What people think?" He was furious. (In retrospect, Elaine didn't blame him.)

"That's not what I meant." She urged.

He wasn't listening. "I thought this was more than that! I would do anything for you, you know that? I'd die for you, Elaine! And you're gonna break things off because some slackjawed, drunken idiots who could't tell their ass form their elbow would gossip?"

Even as he ranted, Elaine knew there was only one way for the two of them to stay together safely.

"Will you change?" She asked suddenly, her voice contrastingly soft but unwavering.


"You said you'll do anything for me? Then will you change- give up being a pirate?" She knew he wouldn't, but she hoped the question would help him see why they didn't belong together.

He stared back for a long time, weighing her question, before slowly shaking his head and mumbling "no." It was laced with heartbreak.

She nodded, taking a deep breath and closing her eyes for a moment. She realized she'd never be able to say goodbye without breaking down, and if he saw that she cared that much, she knew he'd pursue her for the rest of her life. He wasn't one to give up easily, but she hoped if she broke his heart thouroughly enough then she could be done with him. So she told him: "Guybrush, I want to think things over. You should do the same. Go for a walk and clear your head; I want to talk about this."

He knew it was suspicious, but he couldn't put his finger on what it was, so he just nodded and walked out of the room. When he returned less than twenty minutes later, Elaine and all her things were gone.


The young governer was just beginning to forget about Guybrush when he showed up again; this time to her second home on an obscure island. She had fled there because it was a failing island with high crime and a corrupt government. She'd hoped that the work she'd have to do would get her mind off her ex-boyfriend. While she was there, she heard tales of the mighty Guybrush Threepwood and his bold exploits around the Carribean. She assumed this meant that he had taken a similar approach to the breakup and was throwing himself so deeply into his work that he would be too tired to cry himself to sleep.

Until three months later, when he showed up at her door.

"Hi honey." He said, offering a weak smile and peeking up at her through his now-unruly bangs.

Elaine sighed dramatically, trying to decide how to best tell him off. But he spoke before she had the chance.

"I've changed my mind."

"You've what?"

"I'll give up pirating."

"Guybrush... no..."

"Yes." He insisted. "I'll do anything you want. I'll take some boring government job. I'll stop pillaging and sacking. I'll shower more than twice a month. I'll stop bringing monkies into the house. I'll rub your feet every night. Whatever it takes to make you want me again!" He grew increasingly desperate as he spoke and looked into her eyes the whole time, which made the speech and the fact that he was essentially begging by the end even more unbearable than it already was.

"Guybrush, don't- don't do this. It isn't right. Our paths are too different. You're meant to be a mighty pirate, so don't throw that away over me." She forced herself to look him right back in the eyes as she answered. It was harder than she thought it would be.

"But I want to." He said simply.

"No you don't!" She cried, frustrated. She'd underestimated his resolve again, and it was coming back to bite her. Apparently nothing could convince him that they shouldn't break up. At least he seemed to believe that she wanted nothing more to do with him.

"Why won't you leave me alone?" She moaned, defeated.

"Because... I love you."

Elaine felt her heart jump into her throat at the words, and silently cursed him for choosing this moment to drop that bomb on her. After a moment, she regained control of herself and tried to fix the situation. "Well, I don't." It was a lie, she realized even as she said it.

Guybrush knew it too, because instead of looking sad, he smiled a little. "Yeah you do." He chided gently, with just a hint of singsong teasing.

She sighed. Sometimes she forgot how much dealing with Guybrush was like dealing with a child.

He took a step closer. "Come on baby, give me another chance."

She was at a momentary loss for words, so she sufficed herself by shaking her head.

He moved one foot back, and for a brief, glorious moment, Elaine thought he might give up and turn to leave, but instead he swooped down and kissed her.

(Later, Elaine would say that it was the few extra seconds it took her to push him away that eventually changed her mind. Though she didn't realize it until she saw LeChuck's face again, almost a year later, after he had trapped Guybrush in his Carnival of the Damned and she had shouted at him almost without thinking that he was the only man she'd ever loved.)

Elaine lost control for a few moments and kissed him back, letting her hands bury themselves in his blonde hair and basking in his scent of ocean and sweat and grog, before her brain kicked in and she realized that her plan was falling apart. As soon as she regained her senses, she shoved him off with as much force as she could muster, then punched him in the face as hard as she could before her heart could tell her fist not to.

She heard the resounding crack of knuckles-on-eyesocket almost before she saw it, and Guybrush crashed to the ground with an uncraceful thump! She slammed the door on him before he had a chance to look up. She hoped she had looked angry, because as soon as she had clicked the lock into place, she sank to her knees and leaned her head gently against the door, and cried until her eyes were red and she was reduced to hiccups.

"I love you too..." She mumbled through her sobs.

If she hadn't known better, she would've sworn she heard Guybrush's voice drift faintly through the door saying, "I know."

By the time she saw him much later on Booty Island, she'd done her best to lock her heart and throw away the key.