Izaya loves humanity. As a consequence, he's dedicated to its survival.
Only people who value life should live, lest they infect others.
He browses suicide forums at night, and feels sad. It's not caused by pity, but the fact that people like that can exist on his earth and take away his enjoyment just by being there - that's just saddening.
He doesn't think of what he does as cruel. If they were determined enough to live, they would do so. He's pruning the weeds.
He's just honing his skills, so he can try it on someone who actually matters.
1. forum (depressiononline.com/forum/showthread.php?threadid=190028)
The first encounter online is a long game. It's easy pickings, starting on a forum for the depressed, but he has to build up his experience somehow. He introduces himself - playing the game a little closer to his real identity, he calls himself Makoto on the forum. He flirts with an anime fangirl, telling her what Japan is like, posting on all her threads, private-messaging her and telling her to cheer up. Before long she's given her phone number to him, and he sends messages with silly smileys - flailing bears, hopping rabbits - telling her that it's okay and that everything will be better. His phone bill is soaring, and the time zones don't coincide, but the game is worth it.
Somewhere along the line, this shifts to him telling her that it's okay if she thinks she's worthless, and that everything will be better in the afterlife. When she tells him that she's scared that everyone hates her, he doesn't bother to reassure her, but tells her that he'll be there even if everyone does. She's in a downward spiral, and he's her only support. When she's tempted to call a suicide hotline, he calls her instead, drawling out her name, telling her that he's so sorry for her constant pain and depression, and casually mentions that talking to her has been kind of a downer. She sobs on the line to him as he talks about all the other fun things he could be doing.
She sends him a message to apologise for all the trouble she's caused just before she kills herself.
Whenever Izaya gets a new phone, he makes a point of transferring that message.
2. irc (#potheads, irc.woobiedoop.com)
Tanaka Taro mentions it in chat. His friend stumbled upon an IRC channel where someone appeared to be killing himself, and Kanra doesn't even have the time to type passive-aggressive tildes and tease Taro for hanging out with druggie friends, he's firing up IRC as soon as possible and scouring the imageboards for prior logs. He's sure someone must have posted them somewhere - aha, jackpot, and there's a distressed poster talking about that guy's past too - no address yet, he'll have to do a whois for that. Not that he'd show up personally with an Enya CD and even more sedatives, but it would be so much better if he could stick the needle into the vein. No fingerprints, of course, but just the thought of his finger being the one to depress the plunger, to watch a worthless scumbag slowly die - that will stay with him for a very long time.
He reads through the past of Dipper - what an awful name, then chooses a nickname. It should be something fitting for the job, people name their swords, after all. The alerts from Taro's chat ping in the background, but he's on a mission.
Inuko's a good nickname. Feminine enough for him, alludes to Dipper's dead dog (drowned by his father - wow, daddy issues much?). Nickserv is messaged, the nickname is registered, and he is in business.
It's shorter than the first. It takes two hours for him to goad Dipper on, alternately flirting with him and cutting him down with veiled insults, trying to allude to a past that he doesn't even know and hoping that Dipper will be reminded of something unfortunate. He casts doubt on everyone that Dipper's talked to for years and builds himself up to seem like the only person Dipper can trust. Pulls out quotes from a quote dictionary to convince him - and hell, he doesn't even know who half the people he's quoting are, but the point is to make himself seem more knowledgeable and to make death seem like Dipper's only option. Dipper's sentences get shorter and more intermittent, and he starts typing a count of how many sleeping pills he's taken in between pleas from the other chatters.
[kaizer] dipper we've only talked for a few months but i love talking to you please don't do this man
[kaizer] please call the ambulance please
[Inuko] Come on, Dipper, quitting now would be the pussy thing to do.
[Inuko] You're hardcore, aren't you?
[Inuko] A real man would drink some booze.
[HENDY] fuck no dude don't listen to inuko, who the hell is that?
[quadro] dipper please, give us your address so we can call the ambulance
[Inuko] Are you really going to listen to them? Come on, Dipper. Take more. Make it to 50.
[Inuko] This can be the one memorable thing you do in your life.
[Dipper] i think my dad has vodka
[Dipper] 32 now
[Dipper] fuck yea i'm hardcore. brb
The other chatters finally manage to locate his address from old chatlogs and a domain name he mentioned registering once, but it's too late by then.
Izaya makes a note of the name and location they mention, so he can check the obituaries later.
He never did make it to 50.
3. webcam (emopunksunite.net/cam/411152/, cam/413245/, cam/522289/)
By the time Izaya comes across a flashing ad asking him to meet "hot emo camgirls", he's become pretty good. He clicks the link, and thank god it's a free site, a semi good-looking girl is staring at him, makeup meticulously applied on her face, an array of faded scars on her arms. Her t-shirt is stretched tight across her chest. It has a band name that Izaya's heard of, but never listened to, so he searches for the lyrics to one of their less-popular songs. The first few lines are stalling for time until he can read enough about the band to pretend to be one of their fans.
When he quotes the lyrics to her, she lights up, hot pink twin ponytails bouncing with her ample chest.
Thirty minutes later, her mascara is running with tears, and both of Izaya's hands are on the keyboard, alternating between callous one-liners to her, and this really cool online Flash game he's playing where he's a rainbow unicorn. It's fun to watch his words actually affect someone, so he tries to improve on the phrasing, taking notes on what affects her the most. He manages to land on a star, which explodes, and his unicorn trails glitter in the sky as it makes its next leap. He turns down the chat's volume so he can hear the sparkly sound effects. She's crying into the microphone and begging him to type something, but he'll do it later, after he times his jumps just right.
He won't go for the killing blow, it'll take too long, so he switches to another skinny teenage girl with a short blue razored haircut, taking more notes as he goes along.
By the third girl, he's managed to get it down to five minutes before she starts sobbing, leopard-print dyed hair obscuring her face.
Next time he'll pick one with shorter bangs. He likes to watch the pain in their eyes.
He listens to the sobs, and thinks of the one that got away.
0. real life
Izaya's taken weeks to build up Shizuo's trust - doing small favours for him, handing him stationery when he breaks his own in rage, hiding from him instead of slashing him with his knives. Ideally this would last months, but he has a definite timeframe for Shizuo's downfall, and he wants to get it done as soon as possible, before graduation. His ideal timeframe is by the end of this year, where he should finally get the chief of police in his pocket. By that time he'll have a coroner and an ambulance worker at his disposal, and the chief can help to smooth over any discrepancies in the reports.
He's not sure what he'll do about Kiyokaze Mariko yet, but that step can come later. It's an important step, since he first created this plan when he saw the furtive way that Shizuo looked at her. Mariko's a shy one, glasses, wavy black hair with straight bangs, the maternal sort. A new transfer student, so Izaya doesn't have a good grasp of her personality yet. Is she the kind who will go along for a simple bribe, or will she need a little more manipulation? Her bag is looking a bit threadbare, so maybe the bribe. He'll have to arrange to steal her stationery and pretend to have found it, or help her with a similar mundane complication in her life - after arranging it, because he can't leave things up to fate.
In any case. First steps first. Shizuo isn't looking at him with direct hostility, just a stare that makes him very aware of how fast he'll have to be in case Shizuo starts going berserk, and that's a great sign. He has some form of trust.
"So, Shizuo, done anything this weekend?"
This conversation is actually cordial. They chat a bit about movies, and Izaya isn't sure if he should start this now or wait to build up the foundational trust in the relationship. Maybe he could scrap the plan, and they could be friends - that would work, if he actually wanted someone like Shizuo to exist in this world. But even though Shizuo seems to value his life, he irritates Izaya by existing, so hopefully his existence will cease in the very near future. He can't be manipulated, and he can't be bought, but hopefully he can be nudged. Nudged towards a loveless, bleak future where all that's left is a knife, and his bare arm, and his pulsing veins, and Izaya's hand on his shoulder. Reassuring Shizuo and urging him on, guiding his hand to slice vertically downwards.
"How about Mariko from the next class? Great looker, huh?"
Shizuo's stare has lessened in intensity. He cocks his head, perhaps contemplating Izaya, perhaps in agreement. Izaya decides to continue, since Shizuo seems attentive enough for phase 2.
"Kaneda told me you were staring at her during gym - if you want, I could make things easier, maybe introduce both of you."
He smiles congenially. He waits for the subtle shift in body language, the hint of vulnerability, the sign for him to pounce. Shizuo's about to step into the trap, and it's going to snap shut, and there's nothing that can save him from it.
Shizuo edges closer to Izaya, leaning in, and there's a surge of joy through Izaya's body.
Right on cue. He really is good at this.
Shizuo smiles, baring his teeth, as he punches Izaya straight in the face.
He'll probably need to revise his approach.