Characters: Makubex, Edward Wong Hau Pepulu Tivrusky the 5th (aka Radical Ed)
Fandom(s): GetBackers, Cowboy Bebop
Spoilers For: IL arc of GetBackers, Ep. 24 of Cowboy Bebop
The Evidence: At first glance, this pairing looks unlikely just because of the timeline. Makubex was born, well, depending on when you want to claim GetBackers is set, somewhere bewteen 1990 and 2010; I tend to claim 1999, and place the IL arc in August of 2014. Ed was born around 2060 - Cowboy Bebop was set in 2072, and she's twelve or thirteen by then. That 60-year age gap might make a difference.
Or then again, it might not. Neither of them exactly act their age anyway. And an argument could be made for Makubex's being functionally immortal. Certainly, I think he wouldn't have to get older if he didn't want to, once he was able to gain complete control of Lower Town - which it's nearly certain he will, eventually, be able to do.
They have a lot of interests in common - well, actually, they have on interest in common, but it's so big it defines both their lives. Ed and Makubex are both superlative hackers. If they ever met, they'd have plenty to talk about simply on the basis of "comparing notes"; I imagine they would both come out of the conversation with a few new tricks.
However, in terms of personalities, they're almost completely different - and complementary. While Makubex is quiet and withdrawn, Ed is exuberant and outgoing. Makubex is fatalistic and dreads the future; Ed takes each day as it comes, living life on the spur of the moment. Makubex has trouble letting go; Ed never holds on to things when she's tired of them.
But there are a few ways in which they're very similar. Neither of them accepts failure, or is ever so discouraged they abandon something once they have decided they want to see it through. Neither of them lets fear get in their way. Neither of them believes in convention, or authority.
And, of course, both of them are highly intelligent - and, at least partly because of that, very isolated. Although their worldviews are very different from each other's, they're even more different from the rest of the world's. I think they would get along just fine.
Conclusions (a.k.a. Why They Should Meet): In a sentence: they'd be good for each other.
The only person who could really draw Makubex out was Ginji. Ed is a lot like Ginji - she has the same cheerful, carefree approach to life. I think she might have the same effect on Makubex. Similarily, Makubex could provide a "voice of reason" in Ed's life, and give her something she can hold onto, which, if she ever does start "growing up", she's going to need.
After all, what does the future hold for them? By 2073, many, if not most or all, of Makubex's friends will be dead - and that's going to hit him very hard. He'll probably have accomplished what, as of the IL arc, was his overriding goal - freeing the Infinite Castle from the control of the "Gods" of Babylon City. With all the most important things in his life gone, he'll be the lonlienst and saddest he's ever been, still living mainly because it would hurt those of his friend who are still around if he died. Having someone like Ed come into his life would at least convince him it was worth going on.
And Ed? Well, she's left the Bebop. Maybe she caught up with Appledelhi, maybe not. Even if she did, it's not likely she'd stay with him forever - Ed never stays anywhere forever. She doesn't like ti tie herself down like that.
Because of Makubex's being confined to the Infininte Castle and Ed's wandering nature, any relationship they had would of necessity be long-distance. However, considering they'd be likely to meet online in the first place, and that they're both as comfortable with the online world as the phsyical, this probably wouldn't stop them. They could be a great team, too - considering their individual hacking skills, the combination would be incredible.
I don't think, if they met, they could not become friends. They complement each other so well. And one way or another, they'd have fun with it.