Disclaimer: I do not own Fairy Tail. This is my first CanaxGray fanfic, just to let you know.

It was a calm and peaceful day in the Fairy Tail Guild. Gray had liked it like this. Nothing had gone wrong for a while now, and he hoped that it would stay that way.

Unfortunately, those moments of peace were the warning sign of a storm coming. "Hey, Gray! Lisanna and I have been together for three months now! This relationship stuff is awesome!" Natsu's distinctive voice shouted across the bar.

"Do you really have to shout it out?" Gray asked, as he looked somewhat annoyed. It's not that he was mostly irritated by Natsu's loud voice, but Gray was romantically dense. The only woman he had ever bonded with was Ur, but Gray didn't exactly know how to flirt or be romantic in the slightest.

Well, Juvia had been attracted to him for a while now. Although she was attractive, Gray did think she was stalkerish and possessive of him. He felt really down to be single while most of his friends were in relationships.

Mirajane asked with a kind look on her face while preparing a drink for Gray, "What's the matter?" Gray explained to her how he didn't want to feel like a third wheel around his friends, and how he hated this feeling of envy that welled up from within.

"Don't worry about it, Gray. Eventually, you'll find someone that's a great match for you." Mirajane told Gray while placing a booze-filled beer mug in front of him.

"I didn't know you were a jealous chicken, stripper." Natsu said while looking cocky.

"I'm not a chicken at all, flame brain! I'm brave on missions, and I can certainly overcome jealousy! Just wait! I'm sure I can beat these feelings of envy!"

At this point, Natsu and Gray's loud argument had reached the ears of everyone in the guild. They turned to the boys, and a few smirks appeared on the faces of the males.

"If you're manly enough, you should ask out the next available girl who walks through that door." Elfman explained, as he finished drinking from the fifth beer mug at his table.

Gray looked around, and noticed that the males and females had nodded in agreement with Elfman. However, Gray thought about the outcome. What if she was to reject him? That would hurt just as much as the feeling of jealousy.

"Hold on. What if this doesn't work? Besides, I'm not desperate. What if she's unattractive? What if I don't like her personality?" he asked while he still thought out the possible scenarios that could come from doing something like this.

Natsu shouted while looking somewhat irritated, "What if Erza had a moustache? She'd be powerful and look really weird. Look, stripper! For once, act before you think!"

Gray simply sighed, and turned away from everyone while still looking very lonely. He took a few sips of his drink, and he looked depressed. Well, Gray was a reserved person. He preferred to be alone sometimes, and he did tend to come off as somewhat cold towards Juvia when she flattered or was overly loving of him.

Then, the long moment of silence was broken with the sound of the entrance doors to the Fairy Tail guild opening and closing behind someone. Then, Cana walked over to the bar and her eyes scanned the area. She noticed that everyone was confidently smirking at her, and she wondered what was going on.

"Hi, Cana! Gray would like to ask you something." Mirajane told her with a smile on her face.

Well, that's the end of Chapter 1. What will Gray say to Cana? How will she react? Find out in the next chapter. I apologize if it's too short. The next chapter shall be longer.