Killian looked at the bottle of rum on the desk in front of him and let out a sigh. His relationship with Emma had quickly been going downhill and he knew it would soon end completely yet he kept prolonging the inevitable.

"Hook?" called a familiar voice.

Killian looked up to see David stepping into his cabin on the ship.

"What do you want?" spat Killian, not wanting company.

"To talk. You've been so grouchy and off lately. What's going on?" David asked.

"It's none of your business."

"Hook, I'm trying to help you. That's what friends do."

"I don't need your help."

David sighed and shook his head, thinking, he's hopeless.

"Are you sure you don't want to discuss it? Talking helps a lot."

"I said no!" Killian yelled, grabbing the bottle of rum and throwing it at the prince.

David ducked and the bottle shattered on the wall behind him, glass littering the floor.

"Okay! Okay! I get it! You don't have to mutilate me in order to make a point," David said.

He left the cabin and walked off the ship. Killian glared at the door as if daring David to come back through it ever again. His eyes lowered to the shattered glass and instantly felt a pang of guilt in his chest. He'd been too rough with his friend and scared him off. He hadn't truly been angry at David, just with himself. For losing Emma after having come so far with her.

"I'm sorry…" Killian whispered despite David having already left.

Killian grabbed his jacket and hurried out the door and off the ship, hoping to catch up with David. He didn't get far before he spotted David walking into Granny's. He followed close behind and saw David sit down in a booth. He sat across from the prince but was silent, unsure of what to say.

"What are you doing here?" demanded David.

"I… I want to apologize. I'm just under so much stress lately and I guess it's been getting to me," Killian explained.

"What's wrong?" asked David, concern taking over his voice.

"Emma and I have been having trouble lately and I'm worried that soon our relationship will be over. I care about her but we're just not connecting fully," Killian admitted.

"Some relationships aren't meant to be. You need to find your true love, Killian, even if isn't with my daughter. If you know you aren't meant to be with her, tell her. It would be better for both of you if you end it now instead of keeping your relationship growing. She may get more and more attached to you if you don't end it."

"I don't know how to tell her."

"Be honest but not brutal. Tell her you feel you aren't meant to be and that you feel it would be for the best if you each go your separate ways."

Killian sighed and nodded as Ruby approached to take their orders.

"Just a coffee for me, please," Killian said.

"Coffee as well. And some scrambled eggs," David ordered.

Ruby walked away, leaving the two men alone to talk further.

"You need to do it gently, yes, but also make sure you get the point across," David said as their food arrived.

Killian nodded, wishing he could delay it, but knew David was right. The sooner it was said, the better. He ran his fingers through his hair and wished he could disappear.

"Go tell her," David said, nodding, "And don't worry about your coffee, I'll pay for it."

Killian left the small restaurant and went to find Emma. Killian held his breath as he knocked on the door to her apartment, trying to keep in mind that it was for the best. Emma opened the door and Killian let out his breath in a sigh.

"May I come in?" he asked.

Emma nodded and opened the door wider, "Come in."

Killian stepped inside and took a look around, relieved no one else was in the apartment to interrupt them.

"I need to talk to you," Killian started, trying to figure out how to word what he needed to say properly.

"What is it?" Emma asked.

"I… I don't think we're meant to be. I don't see us having a happily ever after together," Killian started.

Emma was quiet, listening.

"I've been trying so hard to avoid this but I feel we just don't fit quite right. I feel you need to be with someone better suited for you. I don't think we should date anymore," Killian said slowly.

"I see…" Emma whispered.

Killian felt his heart breaking but knew they wouldn't work out together in the end.

"I honestly have been thinking the same thing," Emma admitted after a moment of silence, "We weren't meant to have a happy ending together. I'm glad we both agree though."

Killian sighed, "Thanks for understanding."

"Are we still going to be friends?"

"Of course we are. Well, if you want us to be."

"I wouldn't mind."

Killian smiled a little and felt as if a hundred pounds had been lifted off his shoulders.

"You'll find your true love, and so will I," Emma smiled back, "You are admittedly handsome. I'm sure the girls will be lining up at the door to get with you."

Killian chuckled, "I don't know about that but I'm sure I'll eventually find the one I'm meant to be with. She's out there somewhere waiting for me to sweep her off her feet."