I've been trying to think of a way to describe why I ship Jo/Richie. And I know I'm probably the only one who does, so I'm going to try and do what I can to convince others of the pairing.
Let's start with introducing them.
Richie was a streetkid, a foundling, raised in fostercare. He grew up rough, hard and cocky, yet still somewhat naive at the same time. When he was seventeen he'd just started breaking into homes, and stealing stuff. He then made the mistake/fortunate decision to break into the home of one Duncan MacLeod of the clan MacLeod. A man also known as the Highlander.
He did this the same night that said home was also invaded by a less harmless individual known as Stan Quince. This immortal had the intention of catching MacLeod of guard and killing both the highlander and his lover Tessa Noel. Richie was attacked by Duncan with a sword and then witnessed as first Duncan and Stan Quince started fighting and kept watching as Duncan's older kinsman and teacher Connor MacLeod got involved. At the end of the night, Connor told Duncan to keep an eye on Richie. Duncan did so by offering Richie a job and a home. Instead of having him arrested like the police suggested he'd do since this was Richie's last chance at being taken to a juvenal facility, rather than to be caught during an other offense later and sentenced as an adult. In many ways, Duncan became the father/older brother that Richie always wanted.
When Richie was nineteen he was murdered by a thug on drugs out to rob him and Tessa. Richie tried to defend her, but she died regardless of his attempts to do so. Shortly afterwards he came back to life and found out that his friend Duncan had always known he'd one day be immortal and that that was part of why he'd been keeping an eye on him. It took Duncan a while to accept that Richie needed training, but after dealing with another immortal who was in mourning he took up his position as Richie's teacher.
I could go an entire post here, talking about Richie's stunts and deeds. About his heroic nature and how he kept trying to help people, and growing up while remaining some parts of his youthful nature.
Hell I could go on about how a group of mortals, members of an ancient organization that observed and recorded immortals' lives, went rogue and started calling themselves Hunters. They believed that all immortals were demons/evil and saw it as their duty to kill every last immortal out there. Even ones such as Darius who had spent the past millennia and more protecting the innocent, caring for the sick and teaching non-violence.
Richie's worst moment came when his teacher was posessed by a dark quickening. The overload of evil that made Duncan attack Richie and try to kill him. He would have if another friend of theirs hadn't shot MacLeod allowing Richie to escape. This betrayal hit Richie so hard that for a while he started looking for challenges. Headhunting, (aka killing other immortals), just for the need to feel strong enough to defend himself from MacLeod if Duncan ever came near him again.) The two of them managed to settle their issue, but that moment left deep scars on Richie's heart that made it hard for him to learn to retrust MacLeod. (and sure I could also spend some time on how a demon finally managed to get Mac to kill Richie, but hey, I can ignore that if I want to*g*)
Young Jo grew up in that bar, surrounded by the tales of Hunters protecting people,caring for the innocent. She heard about monsters and demons and ghosts and worshipped at her father's feet as he went about saving people. But then one day, Jo's daddy didn't come home. He died in a Hunt she was told. She wouldn't find out until later that it was another Hunter who killed him to end his suffering.
Ever since she was a little girl, Jo wanted nothing more than to be like her daddy. To grow up, big and strong and go hunt monsters, kill evil things and save people. But the people around her who loved and cared about her, treated her like a child without a clue of what she'd be getting into. She finally went on her first hunt and soon came to realize tht the stories she'd grown up with, didn't fully show the danger that the life of Hunting brought with it. And still she wanted to help people.
Even when that worst of things happened, and a man she saw as a friend, who was the brother of a man she had a crush on, came in and told her what had really happened to her daddy. He used her feelings against her and attacked her. It wasn't until the brother came in to save her that she found out her friend was possessed. And she helped Dean, by fixing him up so he could go after Sam on his own. Shortly later her mothers roadhouse was attacked by demons and most of the regulars died in the blast. It was after this that she went back to her mother and the two of them started hunting together. They ran back into Sam and Dean, but Jo knew that Sam wasn't responsible for what the demon inside of him had done. So she forgave him and helped them.
Jo ended up dying in a battle against Lucifer himself. But she went bravely, giving her life to save Dean's as they were on the way to battle the devil. Her mother went out with her, refusing to leave her daughter alone.
So why Jo and Richie. What could these two sidekicks have in common that makes them right for one another? Let's see...
1. They're both tough as nails for one thing.
2. They've both been trained by the best and though their respective teachers/parentfigures tried to shield them from the darkness around them, they're both too much of a hero to let them.
3. They want to help people. Neither of them is in it, just for the thrill, but because they want the world to be a better place.
4. They've both realized that they aren't as strong as they like to think they are, but instead of letting that hold them back, they've just decided to be better and come out fighting.
5. The idea of a Hunter falling in love with an Immortal, a supernatural being that's part of an entire world she woudln't understand. And of an Immortal who had to mourn a man he respected and cared about, who was murdered by Hunters for no other reason than that they believed him to be evil, non-human. I love the idea of the instant conflict. Would a Hunter trust a supernatural being, would an immortal ever trust a Hunter... Who knows, that's where stories come from.
6. Richie is young. For an immortal, he's almost a baby. For a Hunter, Jo is young. They got shielded of from a lot by the people who care about them, but who don't realize just how much darkness they had already seen. That conflict of innocense, of naivety, combined with maturity can only be fascinating to combine, since neither of them is all that much wiser than the other.
7. Jo is gorgeous, sweet when she wants to be, but mostly kick ass. Which is just Richie's type. He loves women that can look after themselves. Richie is cocky, brave, hot as hell and in a lot of ways, very alike to Dean, the man Jo's had a crush on for the longest time. (except that Richie doesn't sleep around as much and actually does want longterm relationships) They both value family, and want someone to help carry the load. They're funloving and I could see them watch one anothers back in a fight, both trying to protect the other. 8. The idea of Ellen trying to decide between the advantages and disadvantages of her daughter dating a guy who can come back from the dead. On one hand, supernatural being, on the other hand, he could and would take a bullet for her to protect her... It would be hard to decide which of the two would win out.
And just think of Duncan's reaction to finding out that Richie is dating a Hunter, and possibly becoming a Hunter himself. His issues with Horton...
The question of how alike or how different both kinds of Hunters are, the moral questions coming out of it...
9. But once they got over those issues, once they accept one another... What better partner for someone like Richie, than a woman who can take care of herself. A young girl who's grown up around the supernatural and would be able to understand what it's like to be with a man who'll never grow older lookswise. What better partner for Jo, than an immortal who can keep up with her in a fight, who can serve as her back up and can and would take the risks to keep her alive. But who's faced enough female immortals to know not to underestimate women. Who better for Richie than someone who understands his need to always carry his sword near him, who'd get that sometimes you have to cut a guy (or woman's) head of, to protect yourself. And who better for Jo, than someone who'd get why she has to carry an arsenal around with her and who wouldn't mind lying to the authorities if it helps them on a case. How better to be with someone who understands that the world can hold dangers that regular authorities woudln't be able to deal with. And for Richie, an outlet for his need to be a hero that would be worth living for.
10. And they just look so pretty together :-)
I don't think I've ever seen anyone other than me who ships this pairing, but if you do decide to write it you can probably post it on sn_crossovers or spnpussypalace