Introduction
This is one pairing that a lot of people are really confused about when I tell people I like it. Sure, these two have never met in canon (and probably never will) but if there WAS a possibility for it to happen, I think it could work. I will now give you the skinny on this puzzling pair!

Wocky
During the game he is seen wearing a fluorescent pink and yellow jacket with pictures of rabid looking foxes on them, and a t-shirt with the Bad Badger on it. According to the artbook, this was to reflect his childish nature, which he indeed has. Being of such nature, he is quite naive about a lot of things- Especially women. He's also quite hyperactive and obnoxious, driving the people around him crazy at times (Poor Apollo didn't know what to do with him most of the trial!)

However, he has quite a good heart, as his father Big Wins says at the end of his trial. Since we haven't seen much of Wocky in the series, it's hard to judge what he was like after Alita's revelation of her plans and her conviction. In my opinion, he's not a bad person at all. His feelings towards Alita seemed genuine, and I can imagine that he was quite depressed when she didn't feel the same way.

Pearl
She's Maya's cousin and quite a spirit medium prodigy. During the course of the series, she is often praised about how powerful her channeling technique is. She was described by Phoenix at one point of having an intense stare. As a kid, others around her said she was very cute and also highly intelligent and refined. Her outfit is the same as Maya's, but she has a very odd hairstyle- pigtails looped like a pretzel.

What would she be like when she is 17-18 (during the time of AJ)? Well, I'll give you my take on it... I feel like for the most part she'd be pretty much the same, except for the fact that she's more aware of the outside world and now knows about her mother's cruel plots to make her the Master, leaving her completely devastated that she would do something like that to her. I can imagine that she would feel very betrayed and hurt because of this.

As for relationships with men, I think she would have gotten out of the whole 'fairy tale romance' thing by now and realizes that not all men are princes. She would also be a bit fearful, since she wouldn't know what to expect and would have to have a lot of trust in them first before she could get closer to them.

How The Two Of Them Could Possibly Meet
Hmm... I've seen several ways that they have met- One where Pearl visits the Kitaki's bakery/pie shop/whatever and another scenario where she meets Wocky at the train station while she's visiting Phoenix and Trucy. I even saw a fic where they met on the Internet. I've seen them meet during the pre-AJ era as well (Wocky being 12 and Pearl being 10). For me, I liked the bakery scenario best, since it's the most fitting.

In my first W/P fic, Pearl had met Wocky because Trucy took her to the bakery his dad started because she wanted her to try their baked goods, since Trucy loved them so much.

In almost all of these scenarios Wocky instantly starts hitting on Pearl, with her reacting either by being shy, flattered, or resorting to slapping him in the face.

How The Two Would Get Along?
Wocky towards Pearl: Like with Alita, he would pretty much be like "Dayum you foine!" He would pretty much do the same thing he did for her as well- Giving her gifts and money, giving her compliments, stuff like that. He would also be very protective of her. However, he'd have to learn that Pearl is pretty independent and isn't as needy as he thinks most girls are.

Pearl towards Wocky: I can see Pearl being very weary of him at first glance- She really wouldn't approve of his gangster background and the things he had done in the past, and she would be overwhealmed by his behavior towards her. But, once she realizes that he means no harm and that he has a good nature, she'd warm up to him.

Advantages
*Lots of room for cute, humorous situations between the two.
*They both come from somewhat troubled pasts, and they could be each other's shoulder to lean on.
*Meep, they just look absolutely adorable together, whether they're kids or adults!
*It's one of the more 'original' ships around- It's definitely not your typical Phoenix/Maya or Phoenix/Iris.
*Makes for interesting fanfiction plots- Come on, a spirit medium and an (ex)gangster? Now that's something new!

Disadvantages
*Most likely impossible to happen in canon.
*Pearl might think Wocky is too immature.
*Wocky might think that Pearl is stuck up and snobby.

Origin
It all started when I was on fanfiction.net one day, looking through the Ace Attorney fics. I decided to see if there were any fics about Wocky because I had recently finished AJ the first time and instantly became one of my favorites. While I was browsing I came across a Wocky/Pearl fic and went "WTF IS THIS?!" Yes. Initially, I thought the idea was downright awful. I had no idea what this person was thinking writing this. So I decided to read it and... I loved it. I couldn't believe how fitting they were together, so I decided to ship it and create a whole fanfic series about them.

Why I Support It
I think this pairing has a lot of potential to work. They were both hurt by someone they loved, and I felt that they could relate to each other in that aspect. I also think Pearl would try to see the good in Wocky, since that's what she does with everyone she meets (Well... Almost). I think she would be grateful of how kind he is to her and realize that she was the person she always wanted to have for her whole life, despite coming in a rather unexpected package.

I also think Pearl could teach Wocky not to be so overprotective of women and realize that not all girls need to be protected. And it would be so sweet if his parents took her in as their own, since Pearl doesn't really have that much family left besides Maya and Iris at this point.

Also, the fact that both of their first appearence cases were VERY similar to each other was downright scary! They both involved a Japanese themed family (Feys and Kitakis), had a doctor get killed (Grey and Meraktis) and his nurse being the killer (Miney and Tiala), a German prosecutor was persiding each case (Franziska and Klavier), a car accident was mentioned (Phoenix and Ini both being victims)... Even DR. HOTTI appeared in both cases. I know he was called Hickfield in AJ BUT STILL. And did I mention that both cases took place in the month of June? AND that they were both the second cases of the games they appeared on? Coincidences? Yeah, but still... Makes me feel like they're more connected than I thought <3

All and all, I think Wocky needs a woman that can set him straight and be a man, and I think Pearl is the perfect one to do that. Wocky could also show Pearl to loosen up a little and not be so serious all the time. It's a win win situation, I think. :3

Songs That Remind Me Of Wocky/Pearl
Differences by Ginuwine This song is mostly in Wocky's point of view, basically talking about how glad he is about Pearl coming into his life and feels like she is the right woman for him... This line especially fits:

I analyzed myself, I was buck wild
(Yeah, c'mon)
Never thought about settling down
But all the time I knew I was ready
(Yeah)
But not with all my friends around

But girl, I put you first now
(I put you first now)
You made me, helped mold me
(Helped mold me, baby)
Turned me into a man, I'm so responsible
(Yeah)
And I owe it all to you

Dreaming Of You by Selena Guess in could be in both of their points of view. The song is about how they're scared to tell each other how they feel:

Wonder if you ever see me
And I wonder if you know I'm there
If you looked in my eyes
Would you see what's inside? Would you even care?

I just wanna hold you close
But so far all I have are dreams of you
So I wait for the day and the courage to say
How much I love you, yes, I do

Angel by Shaggy C'mon, do I even have to say it?! This song just screams Wocky:

Girl, you're my angel, you're my darling angel
Closer than my peeps you are to me, baby
Shorty, you're my angel, you're my darling angel
Girl, you're my friend when I'm in need, lady

Accidentally In Love by Counting Crows They're both kind of in denial about their feelings...?:

So she said, "What's the problem baby?"
What's the problem I don't know
Well maybe I'm in love, think about it every time
I think about it, can't stop thinking 'bout it

How much longer will it take to cure this
Just to cure it 'cause I can't ignore it if it's love
Makes me wanna turn around and face me
But I don't know nothing about love

Speak Softly Love by Andy Williams I don't know what to say about this one... I just feel a lot of Wocky/Pearl vibes from this:

Speak softly, love and hold me warm against your heart
I feel your words, the tender trembling moments start
We're in a world, our very own
Sharing a love that only few have ever known

Wine colored days warmed by the sun
Deep velvet nights when we are one

Speak softly, love so no one hears us but the sky
The vows of love we make will live until we die
My life is yours and all because
You came into my world with love so softly love

Conclusion
Wocky/Pearl may be crack and most likely to never happen in canon, I still think it's quite a nice ship and has a lot of potential to be a meaningful relationship. Two characters that were both wronged and come together to make things right again... *Sigh* So sweet <3