After successfully completing their first operation together (did you expect anything less?), Sly and Carmelita's work relationship really solidified. Over the next few missions, the pair really learned to trust each other and anticipate each other's actions. The Brass took notice of their success and naturally congratulated themselves on their idea to put Sly Cooper on the force.
Unfortunately, things were a little weird for the pair when it came to matters outside work. It wasn't that the two of them didn't like spending time with each other, they just didn't know how to proceed with each other: especially since they currently shared an apartment. Carmelita was totally appreciative of the fact that Sly was a total gentleman and was always knocking or announcing himself whenever he entered a room (and she was sure her parents would have appreciated that fact too, if she ever let them know of her new roommate), but she was starting to get tired of the two of them acting like just roommates.
Sly felt the same exact way and he felt stupid for not realizing earlier the answer in front of him. He needed to proceed like he hadn't had any prior feelings for Carmelita, but that he was developing them for her for the first time. It made perfect sense, in any other situation if he had not known the policewoman, he first would have wanted to get to know her better and have the two of them be more comfortable in each other's presence and be friends before he would have tried anything romantic, like a date. The funny thing he realized was that he already knew her well and was comfortable with her (except of course in this current situation). It sounded easy, but he knew it would be a challenge to get to know Carmelita without letting on that he already knew her that well.
Sly began small and started to ask Carmelita about her taste in music, books, movies, etc. He recommended books for her to read, brought movies home for them to watch, suggested cafes or clubs they could go to as friends. The two got to know each other's likes, dislikes, beliefs, what they each wanted out of life and especially important, those little quirks each other had that drove the other crazy (you never know when annoying each other would come in handy). Carmelita was totally appreciative of this: she desperately wanted to be more comfortable around Sly and was thankful that they were able to start by becoming good friends (though of course she wanted to be more than that, but it does take time), especially since it's easier to share an apartment with a friend rather than just a roommate.
As the time went on, the friendship blossomed and they became more comfortable with each other and started to act more like brother and sister. Many a time, Carmelita responded to some wise crack Sly had said by grabbing his head and giving him a noogie. Then there was the time that they were watching a movie and having popcorn and soda. Carmelita had taken a drink of her soda and let out a burp. She started to flush when she realized what she did, but stopped feeling embarrassed when Sly said, "Nice one, but how about this?" and let out a belch himself.
"Not bad, but I think I can beat that," and she let out a belch herself.
"Impressive," Sly responded. They just laughed and settled back down to watching the movie.
Carmelita and Sly had developed more of a real relationship in the few months they roomed together than in the years they spent chasing after one another
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It was about two months later, after Sly had moved out of Carmelita's apartment (to an apartment in her building nonetheless), that Sly decided that he needed to take some real initiative.
"Hey boss, can I talk to you about something?" Sly asked as he walked into Carmelita's office and shut the door.
"Sure Constable, what's up?"
"I think I have a problem with one of my coworkers."
"What is it?" Carmelita inquired, fire in her eyes, ready to battle whoever wronged her ringtail.
"I think I'm falling for my partner," Sly said and Carmelita thought that she saw his cheeks flush a little as he said that.
"Que?" Carmelita blurted out, not expecting that, though her heart was screaming 'finally!'
"I don't know what our relationship was before I had amnesia, but I really enjoy your company Carmelita, may I call you Carmelita here?"
"Yes Constable Cooper."
"As I was saying, I really enjoy your company, even when you kicked my butt during training, and I've just been really impressed by your intelligence and compassion that you show during our missions, and I've treasured the time we had together when I stayed with you during my training- it gave me a chance to know you a little bit outside of work, so I was wondering if I would be able to have some more time to get to know you even better?"
"Constable Cooper…"
"Please, you can call me Sly here."
"Okay. Sly, are you asking me out on a date?" Carmelita asked with a sly smirk on her face, "Because some officers here may disapprove of a Constable dating his commanding officer."
Sly wasn't expecting that answer and it deflated his hopes immediately. He didn't know what to say and was afraid.
'If she thinks my asking her out on a date is wrong, then what will she think if she finds out I still know who I am?' he thought, really starting to regret what he had done.
"Well,…" Sly tried to reply before Carmelita interrupted him.
"Though luckily, I'm not one of those officers. Not anymore," Carmelita said that last part more to herself than to Sly.
"I've started to realize that rules don't always have to be black or white and besides, I know a few couples here at Interpol, so we wouldn't be doing anything that unusual if you came around to my place at seven tonight."
It took a few minutes for Sly to finally realize what Carmelita had said.
"Se…seven?"
"Yes, will seven work for you?" Carmelita responded with a sly smile.
"Yeah, sure, seven will be fine. I'll see you then," Sly said as he went to open the door to her office.
"Oh, and Sly…"
"Yes," he stopped before he opened the door.
"You don't need to go all out for tonight. We can just go get some pizza or watch videos at my place or whatever. You don't have to do anything special for me: I think that us having some real time together may just be special enough."
"Alright," Sly said, at a loss for words as he left her office, surprised and impressed that Carmelita smooth-talked him for a change.
'Alright ringtail,' Carmelita thought, proud of herself, turned on by seeing Sly Cooper a little humbled by her words and extremely looking forward to that night.
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A little before seven, there was a knock on Carmelita's door and she opened it to see her partner there, carrying a large basket.
"What's with the basket?"
"It's for our date, though I don't want to spoil too much of the surprise right now. And since you told me not to go through too much trouble, you're going to have to do some of the work for tonight, so let's go."
"Fine, do I need to grab anything before we go?"
"You might want to take your jacket," he waited a minute for her to get it before he asked, "Ready to go?"
Carmelita shook her head yes, though she thought to herself, 'Ready? I've been ready to go on a date with you ringtail for years!'
Sly brought Carmelita to a local fine foods store and told her that it was her job to pick out what she wanted for dinner and he'd get what he wanted. Carmelita did notice that as they went through the store, Sly seemed to pick things that he knew she liked. She was touched at his sweet gesture, but decided to play his game and started getting items that she knew he preferred. When Sly saw her doing this, he looked at her and asked,
"Am I that obvious?"
"You're sweet, but yeah, you're totally obvious. Besides I'd prefer it if we ate what we both like, okay?"
"Okay," Sly smiled as Carmelita playfully tugged on his cheek ruff.
After they left the store, Sly took Carmelita to a river front park and they found a spot that had a nice view of the city and set up their 'evening picnic'.
It was extremely romantic, as the two of them ate and enjoyed each other's company while the beautiful colors of the sunset reflected in the water.
As it got darker and the lights of the cityscape in front of them started to flicker on, Carmelita got a little cold and nestled up to Sly for warmth. As she did this, Sly put his arm around her shoulder and brought her close against his body. They enjoyed this moment together before Carmelita spoke.
"Can I be honest with you Sly?"
"Absolutely, there doesn't need to be any secrets between us." (Both of them noted the irony in that sentence)
"I was beginning to worry about you ringtail, it took you forever to ask me out," Sly blushed at that and faced Carmelita.
"Well, yeah, I had wanted to for a while, but I was afraid this might affect things at work, so I had to work up the nerve to ask you out."
"I'd never figure you were one who had to work up the nerve to do anything."
"Well, only when it comes to really important things," Carmelita rested her head on Sly's shoulder as he said this and Sly put his head on top of hers.
"Can I ask you another question ringtail?" Carmelita asked, taking in his warmth and his musk as she was nestled next to him.
"Sure, I'm an open book," Sly replied, intoxicated with the smell of lilac from Carmelita's hair, too taken up in the moment to be aware of the potential danger he put himself in with that reply.
"How long are you going to wait before you kiss me?" she lifted her head and looked seductively into his eyes, though still in his embrace.
"I thought a gentleman never kisses on the first date," he tenderly told her.
"I already know how much of a gentleman you are, now I want to see how good a kisser you are."
Carmelita leaned in and the two of them kissed, really kissed, for the first time (I remember the incident on the volcano, but that was a quick peck, this was a real kiss).
They both reveled in what they had desired for so long.
"Hmmm, that was pretty good Sly," Carmelita gently told him.
"Only pretty good? I'll have to try better next time," and they laughed before setting out for home.
Things naturally progressed from there and Sly and Carmelita enjoyed their time as boyfriend and girlfriend.