(This Chapter Dedicated To @joycesheeran) (You're amazing! :) )

"And so a bomber from World War II would have characteristics such as...?" Toothless' professor droned on about WWII as Toothless slowly started falling asleep. He hasn't been able to sleep well the past month. "Professor?" Toothless sat up, alert and wake.

"No need to call me professor. I, definitely, am not one. What's wrong?"

"Steven asked a question about the bombers that were involved in Normandy. Can you further expand our knowledge of it?"

"Of course. I even have a video." Toothless grabbed a VHS from the overflowing shelves, near the front of the classroom by his student teacher desk, and popped it into the machine. A movie documentary started and everyone silently watched.

"Toothless?"

"Hmm? Oh yes Professor?"

"Do you want to go take a break and rest, I can look after them if you wish. I mean, you only have twenty more minutes until you're done for the day. You barely taught today, but I can see you're tired and so if you want you can leave early I won't mark it against you and make sure the Dean doesn't either."

"Thank you Professor. I'll be in the department office if I am needed." Toothless stood and headed down the hall to his office. Along the way he checked his flip phone and saw Hiccup had called. He started listening to the messages and entered the office. "Hiccup?"

"Hi Toothless. I really needed to talk, so I kinda broke in." Hiccup stood up from the chair he was sitting on and walked over to give Toothless a hug.

"I just-I just got your message. I'm so sorry Hiccup. Do you want a cup of coffee? Tea? Warm water? Can I get you anything? Anything at all?"

"A good job and a loving girl friend."

"Not as reasonable as I hoped but could be worse." Toothless sighed

"You're the mature one, What should I do?"

"I had to become mature to look after you! I'm not the old wise man in the mountain. At least I hope you don't look at me like that." Toothless rubbed his hand against the back of his neck and collapsed into one of the arm chairs facing a large floor to ceiling window overlooking the run-way. A small one propeller plane was just landing. "Hic?"

"Yea Tooth?"

"Do you ever wish you could just do more?"

"What do you mean?"

"I want to fly."

"But you can't."

"They can't keep that as my excuse forever." He kept staring through the glass and out towards the sky, willing his mind to wander to the clouds and the far expanses of the cloud-filled sky.

Hiccup sighed and leaned against the counter top, "I was a wreck Toothless. At least you have your job."

"That's not enough."

"God. You're so effin selfish. The grass isn't always greener on the other side Toothless!"

"What do you know?! Have you been a-a-a... a cripple all your life?!" Toothless stood quickly and had to sit back down, his head between his legs. He focused on clear deep breaths and shut his eyes tight. Hiccup didn't make a move to help him. If he did, Toothless would push him away.

"Toothless," Hiccup talked in a low soothing voice, "You gotta calm down bud. It'll only get worse. I'm sorry I didn't realize- I'm just in a runt. With Merida and my job, I mean I don't know where to turn and now I just- I'm sorry. I didn't know who to turn to and you're my best bud. Please don't do this to me." Hiccup was crying now and Toothless' phone had started to ring.

Taking one last deep breath, he looked at his phone. Then he looked up at Hiccup, tears in his eyes, "It's Merida."

"I can't answer it Toothless."

"Do it."

"What if she hates me? What if she just wants to brag?"

"Why would she do that Hiccup? Honestly tell me why Merida, your Merida, would ever do that to you."

"Give me the stupid phone." Toothless tossed it to Hiccup who caught and answered it, "Yes?"

"Good to know yer still alive, ye stupid." Her voice cracked, she had been crying. But she sounded relieved to hear him. "Hiccup, what happened?"

"Merida, I-I screwed up. I lost my job. I lost you. I hurt Toothless. Imma screw up."

"Hiccup, that's suicide talk. You didn't loose me."

"Well, maybe it is."

"Don't be like that Hiccup." Merida pleaded, "Don't. Please don't."

"Merida, I want you to know that ever since I saw you at that coffee shop, I have thought you were the most beautiful amazing girl in the whole world. I love you." Hiccup hung up

"You're not killing yourself."

"You're right. I'm not."

"How could you tell Merida that you were?!"

"I was referring to the relationship. I was killing the relationship. I don't want Merida to feel guilty or anything. I think she should be happy with her new relationship. I don't want to be the strings to tie and hold her back." Hiccup walked over to where his bag was lazily thrown on a table and picked it up, "I have to go. I'll see you later Toothless. Thanks buddy."

Toothless heard the door close and waited a minute before running out after his best friend. He knew what Hiccup meant by 'kill the relationship'. He couldn't let him die.

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Merida weeped bitterly on Flynn's couch, the same couch that Hiccup had sat and cried on hours before while deciding which to watch: Flip or Flop or The Bachelor. Both had to do with either his job or his girlfriend. But neither existed now. Merida didn't know that though. "Hiccup!" She sobbed until the point where no more tears came and all that was left was streaks of the salty liquid on her cheeks and her small hiccups. "Maybe it was for the better?" She spoke aloud to herself and felt sick. Rushing towards Flynn's bathroom, she hit a picture on the table near the hall. A picture fell and crashed.

Inside, smiling in the frame, was Merida, Rapunzel, Jack, and Hiccup. Flynn had taken the picture. They were on some sort of pirate-themed cruise. She only glanced at the picture, more tears somehow forming in her eyes, and ran towards the bathroom.

Little did she know, one of the four would fall. Or, moreover, jump.