Disclaimer: I do not own Fairy Tail.
A/N: Technically this doesn't count as a new story because it started off as a request on "Romeo's Life" and a number of people PM and review me about it becoming a full individual story. Cana will be the first one, then maybe Lisanna or Mira.
Chapter 1
Ex-girlfriends and Unexpected Confession
Magnolia X797
He blames his dad for the situation he was in right now. If it wasn't for all the times he had to come and pick him up back in the day from the tavern down the street from Fairy Tail, an19-year-old Romeo Conbolt wouldn't be standing in front of said tavern at two in the morning because his mini-lacrima number was at the top of the barkeeper's contact list.
But he wasn't here for his father cause that would be too easy. No, he was here for one of the other residential drunks of Fairy Tail.
He lowers his head in exhaustion and staggers through the front door. His body still ached from the job he had earlier today alongside Max and Alzack which involve protecting their client from a dark guild attack. As he moves toward the bar he instantly sees his objective, for sitting there in her tight jeans and blue bikini top was the miserable sight of a depress Cana chugging down a pint. If the barkeeper's face was anything to go off of, it wasn't her first and it certainly wouldn't be her last if Romeo didn't intervene.
But there was an old saying in Fairy Tail that only a fool (or an S-Class mage) got between Cana and her beer, and Romeo sure as hell wasn't a S-Class yet, though the exam was coming up, this year might be his year, so maybe he was a fool.
"Give me another round, damn it!", The Card Mage roared as she slam the mug on the counter, "I'm going to drink until I forget the fact that I got dump AGAIN!"
"So the rumors are true", Romeo thought as he steps silently behind her though at this point he could stomp all over the place and she still wouldn't notice him. He sits down in the stool next to her and takes a good look at her. The scowl on her face remind the Rainbow Fire mage of Guild Master Laxus back in the day but Romeo could clearly see the tears streaming down her face.
"Cana", Romeo says catching her attention and causing her to snap her head at him and almost instantly her expression changes from anger to irritation.
"Ah crap, what's the baby boy doing here?", she whines loudly, "Daddy finally let you out pass your bedtime?"
The insult simply bounces off Romeo who kept a neutral look on his face. He gotten used to these types of comments over the years. Despite the fact that there are now younger people than him at the guild, he is still refer to as one of the "baby" of Fairy Tail alongside Asuka, mostly because they grew up in the guild from birth. It would seem that a lot of the newer, older, members resented this, thinking that Romeo and Asuka got special treatment from the guild veterans and especially Laxus.
"You do realize that I have been having my own apartment for the past two years right?", Romeo ask.
"Probably have your mom come and clean it for you, don't cha?", Cana grumble.
"Nope, she and dad are too busy taking care of Juliet", Romeo points out. It was some time after the war with the Alvarez empire that Macao realize that he had to man up and change things around if he wanted to get back with Enno. So he tracked her down to her place in Crocus and went to go see her. Romeo doesn't know the details (he was smart enough not to ask) but a few months later his mom came back to Magnolia and back into his life.
It was awkward at first because Romeo has gotten used to the fact that it was just him and his dad at the house and now his mother was there too. Half a year later Romeo is standing alongside the rest of the guild at the cathedral as his father and mother renew their vows and got remarried. Almost a year after that and Romeo is welcoming his new baby sister, Juliet Conbolt, into the world.
He loves Juliet as much as any brother could, but he also realize that his parents probably didn't have enough room in their lives (or in the house) for two kids so he made the choice to move out into an apartment once he turned seventeen. Both Macao and Enno try to convince him otherwise that he didn't have to do this but his mind was already made up by that point.
Anyway, back to the matter at hand with Cana.
"What happen now?", he asked only to see her face contort into seething rage.
"HE DUMP ME! THAT SON OF A BITCH DUMP ME!", she scream as she slapped her mug on the table, this time shattering the glass, "SAID THAT I'M TOO OLD TO BE ACTING THE WAY I DO!"
"You're thirty-one", Romeo states.
"I'm twenty-four!" Cana argue.
"Yeah, funny thing about your age", Romeo chuckles, "It doesn't stop just because you were frozen in time for seven years."
"Bite me!" Cana tells him while flipping him the bird, "I still look as good as the day I left for Tenrou all those years ago."
Romeo's eyes scanned over Cana's body and he quickly came to the same conclusion. Cana's body was the stuff of fantasies.
"Those jobs she's been taking have definitely kept her in shape",Romeo thought as he tune back in to Cana's rant.
"First Laxus dump me!" Cana rage at the ceiling.
"He was taking on the title of Guild Master", Romeo reminds her, "He felt that if he kept you as a girlfriend, every decision involving you would be seen as favoritism."
"Then Baccus dump me!", she continue on.
"That's because you finally drunk him under the table. You hurt the man's pride and with the guild he belongs to, that means a lot", Romeo says.
"And now Daniel dump me!"
"I honestly don't know what to say about that", Romeo shrugged, "I didn't know the guy all that well. All I know that it was your first attempt dating a non-mage."
Cana snaps her head at the Rainbow Fire mage and narrows her eyes in a glare.
"You seem awfully happy over the fact that I got dump", Cana notice.
"I do find your reaction to it funny", Romeo smirked.
"You have no room to talk!", Cana screams as she stands up and shoves a finger in Romeo's face, "Far as I know, you been dump-" Cana started counting on her fingers and recalling past memories, " Four times!"
"Dump isn't the word I would use, but yes, I as of now have four ex-girlfriends", Romeo told her, "All them just so happen to be from different guilds."
"First there was Wendy", Cana put a finger up, "No one was surprise by that and Mira nearly had a heart attack."
"Good times, we started off as a team after the Alvarez war, doing jobs and whatnot. Sometime later I ask her out and things went from there for about a year" Romeo recalled.
"Yeah, the day everyone found out you broke up was the day Mira almost flooded the guild with her tears, almost putting Juvia to shame." Cana asks while sitting back down, "So what the hell happen?"
"Things started getting awkward for us. One day Wendy told me that it was getting harder and harder to see me as someone other than the six-year old boy she left behind when she departed for Tenrou. Add in the fact that she was basically over four hundred years old and you pretty much get the gist of the problem she was dealing with.", Romeo confessed, "We broke it off cause we felt that eventually this would affect our relationship as guild members and our teamwork."
"Must have been tough", Cana commented.
"It was at first but we ended on good terms and even to this day we still occasionally do jobs together, just the two of us", Romeo admitted, "She even helps me babysit Juliet when my parents go out."
"Okay, then what about-" Cana started to talk before Romeo held a hand up.
"As must as I love talking about my past love life, can we continue this conversation while I take you home? I would like to get some sleep tonight."
Cana thinks on it for a moment before deciding, "Fine, but only on the condition that we go over all of your ex-girlfriends."
"Fine, I got nothing to hide", Romeo agreed, "If it gets me into my bed sooner rather than later."
"Let's go then", as Cana reaches into her card pouch and pull out some jewels.
"This is for all the trouble I caused", she says to the barkeeper before putting them on the counter and grabbing Romeo by the arm.
"You don't have to drag me!", Romeo yells as he pulled out his stool and toward the door.
"Yeah whatever", Cana says as the two of them leave the warm bar and enter the cold Magnolia's night.
"It's freezing out here!", Cana complains before she suddenly see Romeo's hand light up in flames.
"You should really consider wearing more clothes around this time of year", Romeo says as Cana moves closer to him.
"I'll think about it", Cana said as she warm her hands, "Now tell me about Wakaba's girl. What happen there?"
"Lindsay?", Romeo said as the two starting walking, "That was something else. She came to me like two months after I broke up with Wendy. She kicked open my bedroom door and damn near ordered me to be her date for some dance that Twilight Ogre was holding."
"She needed a date for a guild dance?", Cana questioned.
"I wondered the same thing. She said that everyone else was bringing a date and she didn't want to feel left out, said that all the decent guys at her guild were already taken", Romeo said.
"And you believe that?" Cana says as she raises an eyebrow, "You actually fell for that?"
"Why wouldn't I? We've known each since before we could walk or talk", Romeo answered, "So I was caught completely off-guard when she kissed me out of nowhere while we were slow-dancing, and then she confessed to me, right then and there while I was still recovering from shock."
"That must have been a sight to see" Cana said.
"She had a crush on me since we were eleven years old", Romeo kept going, "And I never notice."
"Most guys don't", Cana added.
"For a brief moment I thought to myself that this must have been how Natsu and Gajeel felt when Lucy and Levy confessed to them", Romeo admitted, "Like I should have pay more attention to all the things she said and did over the years then maybe things would have turn out differently."
"Would things have turned out different?", Cana asks as the two pass over a bridge, "If you would have known sooner, you think you two would still be together?"
Romeo ponders the thought for a moment before shaking his head, "Nah, we would have still broken up. Sure, we dated for a year, but the one of the problems with dating your childhood friend is that in the deepest confides of your mind, you still see them as just a friend. It took us than half a year to fully transition from being friends to being boyfriend and girlfriend and even afterwards thing were still awkward between us."
"Awkward how?", Cana wondered.
"We live right next door to one another; have ever since we were babies. Our parents knew one another and therefore they knew us", Romeo started to explain, "There were no secrets between us because we knew everything about one another. Public displays such as holding hands and kissing were awkward, going to social events as a couple were even more awkward, pretty much everything was uncomfortable for us."
"So basically nothing change between you two?"
Romeo couldn't help but smirked, "There were some changes."
Cana punches him in his shoulder.
"Hey!", Romeo said as he rubbed his the spot where the hit connected, "It's not my fault she kept the window open more often when she was getting change and it's not my fault my window is right across from her."
"You're your father's son", Cana laughed before wondering, "Hey, everyone knows you and Wendy never went that far into your relationship because ya'll were too young, but what about you and Lindsay, if you don't mind me asking?"
A sad smile appears on Romeo's face as he stop walking and looked up at the night sky, "The night we decided that we were going to take the next step in our relationship was the same night we broke up. We were in my room that night. Both our parents were out of town visiting relatives so that just left me and her home by ourselves."
Cana, surprisingly decided not to make a joke.
"We were both just laying there on my bed, looking at one another without a shred of clothing on. We were both just waiting for the other one to make the first move and we laid like that for two hours before I got up and started putting my clothes back on", Romeo said.
"What did Lindsay do at that point?", Cana asks.
"She got up and did the same thing. Then she gave me one last kiss and went home", Romeo replied, "The next day we were back to being just friends again, almost as if the last year never happen."
"Just like that?", Cana asks.
"Just like that", Romeo repeated, "We both knew that if we would have taken that final step that night, we could never go back to being friends again, never go back to being what we were before we started dating."
"I'm actually sorry to hear that", Cana confessed.
"Don't be", Romeo told her as he started walking again, "I may have lost my girlfriend that night, but at least I got to keep my best friend."
"Your third girlfriend caught everyone by surprise," Cana said, wanting to change the subject as quickly as possible, "Chelia Blendy of all people."
"I'm not surprise by that", Romeo admitted while chuckling a little, "She surprised me when she asks me to go out on a job with her."
"Going undercover as a young couple at a hotel resort in order to capture a wanted dark mage", Cana recalled.
"She wanted someone who wouldn't be all goo-goo gaga over her and I was really the only choice for her who was around her age", Romeo said, "Surprisingly it was Wendy who suggested me to her, say she wanted someone who she knew would have Chelia back seeing how she just got her magic back after not being able to use it for a few years."
"And just like a cheesy romance movie, you fell for her and she fell for you", Cana pointed out, "You two danced together, laugh together, even went out for a midnight swim together. You slowly wormed your way into her heart."
"Yeah and she wormed her way into mine. Granted me and Lindsay ended our dating relationship three months prior and Lyon married Meredy a year beforehand, so I guess both of us were still recovering from broken hearts, her more than me", Romeo said.
"But that kiss you and her shared after the climax battle with not one dark guild mage, but his entire guild as well, was on the front page of every newspaper in Fiore", Cana said, "You can't tell me that you didn't enjoy that."
"Oh trust me, I enjoyed it", Romeo smiled, "Chelia was a great kisser. And just like Wendy and Lindsay, we dated for a year before finally breaking it off."
"Seems to be a thing with you and having a girlfriend for a year", Cana noticed, "Think you might be curse?"
"Maybe", Romeo shrugged, "I have fought mages who were proficient in curse magic before."
"Moving on pass that, why did you guys break up? Cana asked.
"Something happen that I really should have saw coming. She still was hung up on Lyon, whether she knew it or not", Romeo said.
"You do realize I can't read minds like Warren, right? Please elaborate."
"I guess is the best way I can explain is that subconsciously she still hadn't gotten over Lyon yet, even though the two of them never dated ", Romeo explained, "It started off small, with her making tiny remarks about Lyon here and there, and then it got to the point where she was comparing me to him and trust me it was never in a positive light."
"Well that sucks", Cana said, "Why did you stay with her for so long then if she was doing that?"
"I guess after things didn't go well with Wendy and Lindsay, I wanted to try and make that one. So I endure it", Romeo answered, "But it turned out to do me more harm than good."
"How so?"
"It hurt my self-esteem for a good while, mostly because it was no different than all the times I was being compare to Natsu", Romeo said his voice getting a little quieter as he talked, "Anyway we both sat down and talked about it and decided that it was best that we go back to being just friends, or whatever we were beforehand."
Romeo looks back up at the sky while trying to remember something, "Which was a good thing because when we were dating things were awkward around Wendy, seeing how she was Chelia's best friend and my ex-girlfriend. And with the whole blow to my self-esteem I don't talk to her as much as I do Lindsay and Wendy."
"Make sense, I guess", Cana commented while looking down the street and seeing that they were nearing her place.
"Well, it seems that this night adventure is almost at a end, but before we part our separate ways, why don't you tell me about your fourth and final ex-girlfriend, Beth Vanderwood of Mermaid Heel?", Cana asked in a mock noble voice, "I never expected you to date a girl like that."
"You and me both, a city boy like me getting with a country girl like her", Romeo confessed, "I don't think even Carla could have predicted that."
"How did you two hook up?"
"Erza and her friend, Millianna, set us up on a blind date. I was down in the dumps after Chelia, so Erza tried to cheer me up. For Beth, the girls at her guild were trying to break her in to the dating game with someone who they knew would treat her right", Romeo answered, "And I guess the girls in our guild alliance talks amongst themselves."
"That we do", Cana added.
"So anyway, they set us up on a date at some fancy restaurant in Crocus during that year Grand Magic Games; you know the one that somehow ended in a six-way tie between our alliance", Romeo continued on.
"Oh yeah, that was weird", Cana recalled.
"Yeah it was, so anyway the date was as unorthodox as it could be as I noticed that Beth wasn't really all that comfortable dressing up in fancy clothes and wearing make-up, even though to this day I still think she looked amazing", Romeo said as they pulled up to Cana's front door, "Anyway we left the restaurant and decided to go to the amusement park instead. We both had a wonderful time and we started dating from there."
"So for the fourth and final time, how did things go wrong?", Cana asked.
"She was simply too much for me", Romeo admitted.
"Say what?"
"She was the only one I ever took the next step with and it turn out that she liked being the dominant one in bed and eventually in the rest of our relationship", Romeo confessed, "She went from the sweet, polite girl that everyone knew to a overbearing, paranoid girl. At one point she thought I was cheating on her due to the fact that I still went out on jobs with Wendy or the fact that I still hung out with Lindsay."
"Oh did that hurt your male's pride?", Cana teased causing Romeo a tick mark to appear on his forehead.
"Seeing how the relationship I had with Chelia deeply scarred my self-esteem, yeah it did!", Romeo snapped catching Cana by surprise, "Believe or not, I'm all for equality in a relationship. With Wendy, Lindsay, and Chelia we each had one leg in the pants in our relationship, but with Beth she wanted to be in control and after a year I couldn't take it anymore. Deep down I knew it wasn't her fault; she never been in a relationship before so she didn't think her behavior was wrong. So that's why I let her down gently."
Romeo for the third time tonight looked up at the sky while talking, "I told her that she comes on too strong and while that might work at Mermaid Heel, it doesn't always work out in a relationship. Surprisingly, she confessed she knew what she was doing and was only doing it because she didn't know how to act in those types of situations. Apparently, her fellow guild members, especially Kagura, were constantly telling her that she had to wear the pants in our relationship and she took their advice too seriously."
"But you still broke up with her", Cana said.
"Only after I told her that she need to start thinking for herself", Romeo explained, "I also told her that it was partially my fault because I was still trying to get over Chelia and the blows she dealt to my ego and I probably shouldn't have gotten back into the dating game so soon after breaking up with her."
"So how are things with you and Beth now?"
"We occasionally talk", Romeo replied, "She's taking some time off from dating and is focusing more on improving her magic so she can help her guild out."
"These past few years have been rough on you, Romeo", Cana said after the two stood in silence for a moment, "Breaking off four relationships within the span of four years, including one with the girl you developed your first crush on."
"Yeah it has been tough for me", Romeo agreed, "Seeing how-wait what?"
Romeo turns to stare at Cana with a baffle look on his face.
"What?"
"What did you just say?", Romeo asked, "Just now."
"About how you had a rough four years?", Cana said.
"No, after that", Romeo says.
"About you breaking off four relationships?"
"Keep going", Romeo says.
"You mean how you got dumped by your first crush?", Cana asks.
"Yeah that one", Romeo said, "What do you mean by that?"
"You got dumped by Wendy, your first crush", Cana said, wondering why she has to explain this to him.
"Wendy wasn't my first crush", Romeo said.
"Really? Everyone thought for sure you had a thing for her when she got back from Tenrou especially Mira."
"I don't know why, I didn't develop romantic feelings for Wendy until after we started going out on jobs together", Romeo told her.
"Okay, then was Lindsay your first crush?", Cana asked.
"No."
"Chelia?"
"Still no."
"So Beth?"
"I only said that she looked amazing on our blind date, but I never really talked to her that much beforehand, so no", Romeo said.
"Then who was your first crush?", Cana asks, now curious to know.
"It was-", Romeo started to say before shutting his mouth and Cana noticed that his face was turning bright red.
"Never mind!", Romeo said as he turned around and starting walking away, "You have a good night, Cana!"
Suddenly he feels a hand grab him and pull him back. He turns around to see Cana latched onto his arm with a devious smile on her face, "Oh no you don't!"
"Let go!"
"Oh no, not until you tell me who your first crush was on!'", Cana demanded.
"It's none of your business!", Romeo roared and tried to pull away but the Card Mage was latched on tight and Romeo was soon dragging her along the road.
"Let me guess, it was Mira! It's always Mira for most of the guys in the guild!", Cana said.
"Let go Cana! And no, you think I want to get stab to death by Freed?"
"Or was it Lucy?", Cana continued on, "She always did flaw her stuff!"
"This is getting old, Cana!", Romeo yelled again, his patience nearing its end, "And Natsu would burn me alive if he found that out! You know how overprotective he is of her nowadays!"
"Or maybe it was Kinana! Everyone knows you two have a brother/sister type of relationship with one another!", Cana pressed on.
"That's enough Cana!", Romeo screamed, "And I rather not have to check my meals for poison!"
"Was it Levy, you like those bookworm girls?"
"Gajeel would break my legs, so no!"
"Evergreen, her bitchy attitude excited you?"
"No! I do not want to get pummel to death by a beast arm!"
"Is it Lisanna and her catgirl transformation?"
"I like my soul inside my own body, thank you very much! By the way you can let go of me anytime now!"
"Juvia and the way she refers to herself in third person?"
"I don't want my nuts frozen off, so hell no!", Romeo said while still dragging Cana.
"Or maybe it was Bisca in all her sexy milfness!"
"That is just wrong on so many levels that I don't even know where to begin! She used to babysit me and I rather not be used for target practice by Alzack!"
"I know, it was Laki because you had a thing for girls in glasses!"
"Do I look like a masochist to you?"
"Wait, wait! It's Erza because you have a fetish for chicks in armor!"
"Yeah, cause I so want a highly powerful, ex-criminal on my ass! Are you ever going to let go?", Romeo roared, now feeling like he was about to snap.
"No! If it wasn't none of them, then maybe it's the girls from-" she started to say before finally…
"IT WAS YOU!", Romeo's voice echo across a quiet Magnolia, "YOU WERE MY FIRST CRUSH!"
...
...
...
Cana and Romeo both stand there in silence for what seem like a eternity, with Romeo unable to make eye contact with her. Cana's shocked expression conveys all the emotions she was feeling right at that moment after Romeo's starling confession. She was frozen solid; all she could do was stand there and blink.
"What?", she said softly in a voice that was barely above a whisper.
Romeo removed his arm from Cana now relaxed gripe and after five more minutes of continue silence the Rainbow Fire Mage brings his head to look Cana in her eyes.
"I should probably be going", he said in a quiet voice.
Cana slowly came out of her daze and turns her full attention to Romeo, "How long?"
"Excuse me?"
"How long have you had this so-call crush on me?", Cana ask again.
"It started a short while after you got back from Tenrou", Romeo confessed.
"And when did it stop?"
"After you started dating Laxus."
"I started dating Laxus around the same time you formed a team with Wendy", Cana pointed out, "That was over two years after I got back."
"What was I suppose to do? Tell you to your face?" Romeo said as he adopted a cheerful personality, "Hey Cana, having fun chugging there? By the way, I have the biggest crush on you."
Cana actually snorted at this, "Okay that would have been weird."
"You see", Romeo smiled.
"So out of all the girls in your life at the time, it was me you were the most attracted to? What brought this about?", Cana had to know because even she knew that she wasn't the best role model around.
Romeo had to think on the answer for a moment before speaking, "You were different."
"Understatement of the century", Cana joked.
"No, I mean you never try to change yourself over other people. Not for Laxus, Baccus, or that Daniel guy. I mean Juvia tone down her stalking habits once she and Gray got marry. Evergreen stop being so bitchy once she and Elfman started a family; and to everyone's surprise even Gajeel and Natsu tone back their destructive behavior once they were married."
"You're saying it like it's a bad thing that everyone's negative traits went away upon them getting with someone", Cana commented.
"Oh no, the guild's a little better off with them being more calm, though I do miss the occasional brawl sometimes", Romeo admitted.
"But back to me", Cana said.
"Yeah like I said you never changed", Romeo continued on, "You're loud, a party animal, and you couldn't care less of what other people think of you."
"I'm not exactly the girl you want to bring home to mommy", Cana chuckled.
"But you're the type of girl who not afraid to show her true self", Romeo added.
"You're damn right about that!", Cana proudly boasted, "Ain't a man alive who can tame me! If Laxus and Baccus couldn't do it, then no one can!"
"Sounds like a challenge", Romeo smiled causing Cana to give him a look.
'Whoa there cowboy, I may not be a "proper" girl but even I don't go out looking for a new boyfriend the same day I got dump by my old one."
The two shared a laugh at that statement, the awkward tension between them from Romeo's confession completely vanished.
"Don't worry, I'm not ready to get back in the dating game just yet", Romeo told her, "Might take a while before that happens."
"So there's no awkwardness between us? We're still good friends?", Cana asks.
"Of course, I merely told you that I used to have a crush on you; I didn't confess my undying love for you", Romeo stated, "Tomorrow, we'll share a laugh about this at the guild. In fact, I'll pay for your drinks."
"I'll hold you to that and you better bring a lot of jewels!", Cana smiled as she walked back to her place, "Catch you tomorrow, Romeo!"
"See ya!", Romeo called back as he watched her walk away, his eyes never leaving her retreating figure, not even for a second. It was only after she closed the door behind her that he realizes what he was doing and took off down the road.
"Wow, Laxus and the rest of those guys were idiots to dump her", Romeo said as he turn around and started walking, "A free-spirited girl like her is hard to come by nowadays."
He stares up at the moon as he strolled down the street, his mind a jumble mess.
"It would have never worked out between us anyway. A girl like her doesn't need a nice guy like me", Romeo told himself, "But it's nice to wonder sometimes. Besides..."
Unbeknownst to the Rainbow Fire mage, Cana was watching him leave through her downstairs window…
"He certainly has grown over the years, hasn't he?", she said to herself as she smile, "Those girls have no idea what they gave up."
Her smile fades away as Romeo rounds a corner and disappears from her sight.
"Get your head out of the clouds, Cana. He only said that he used to have a crush on me, nothing more.", she told herself as she looks skyward at the moon, "Romeo needs a nice girl in his life anyway, not someone like me. Besides..."
"I'm probably way too old/ too young for him/her", they both thought at the same time.
That night silently went by without any more incidents, but for those two mages the next morning would bring a whole new slew of problems and unexpected emotions.
A/N: This story's not over it's just that there are a lot of issues they each have to get over before they even consider dating, I just thought I change the ending a bit. Notice how they both said that they were too old/young for the other person not the other way around.