I like this prompt and I’m taking my own crack at it. [Link]
To answer this question I must first break down two main factors.
The first being who are you?
As he often has said, ‘he loves humans,’ but as anyone knows he means the group, not you specifically. HOWEVER. This prompt enters a very important term and that S/O. A Significant Other. Does Izaya have such a person canonically? No. Would he canonically? It seems Narita would imply no? That’s part of Izaya’s assholeish charm. Regardless of this, the question is again, IF.
So IF Izaya had a significant other, and IF he found them crying, what would he do?
Thus brings into question the second factor to this,
is izaya capable of comforting?
Izaya is not simply the type to take selfishly. Despite the big bad evil persona that gets built around him he is a giving sort as well. But how that works out can be up to his whims. He will just as easily steal from the rich to help the poor as he would hurt the poor to benefit the rich. And neither is done with malice. As Nakura once said, in the same way someone looks at a cat and thinks ‘how cute’ Izaya would openly say the same of humans, be them happy, loving, miserable, or dying. To this end we know, his love is without restraint and without cause. He simply loves and that’s that. But is his love comforting?
His love is for everyone, and thus one would think his love is vast and great, but it’s rather shallow. His love is the act of distancing himself from humans. “I accept all they are, the good the bad and the ugly!” By doing this he has effectively distanced himself from them. Its a self defense. By being ok with anything, he doesn’t have to expect anything, or want anything. And thus can’t be hurt as a result. Shinra remarks that if you filled Izaya’s heart with love or rejection that it would break. I think Izaya is rather fragile and wouldn’t know how to be deeply loving without first putting himself at risk. Which he’s shown he’s not capable of doing in the series. (his spin offs.. maybe. havn’t got there.)
So despite his love being shallow, how do others react to him. Well among others, Saki is referred to as being someone he has rescued from a difficult living situation. She then basically devotes her life to Izaya. Extreme, but no one would do so without having cause. If Izaya was simply a cold unfeeling selfish asshole, he wouldn’t just help a random girl when the benefit to that is so low. Also its a money drain. Also also he doesn’t care if he’s loved back so his motivation for helping is purely cuz he just wants to. And her own response is gratitude. Why? Well honestly, perhaps Its because she found comfort. Izaya made her, and others, feel safe. Not all comfort is hugs and cuddles, some times its words of affirmation, sometimes its acts of kindness. Such things that I do think Izaya is good at.
With these two points in mind: What would Izaya do if he found his Significant Other crying?
As simple as that is it’d be his first instinct. He’s an informant after all and he excels at that. He’d get to the bottom of what happened, and why it happened. Knowing what has made you cry, he can start to make a structured plan on what to do.
--Rough day at work? Same. Sounds like something a bit of tea and talking it out can fix rather easily. That and maybe he could use a break too. And even if he has his phone out and is still working, he is adept at multitasking and is listening even if you aren’t always sure. And he would make you very aware of that by being engaged in the conversation still.
--Tripped and got hurt? Ouch, looks like that hurts. He has a small pharmacy of medicines from Shinra for any need he might encounter, patching up your aches is simple enough. He even knows how to manage that himself as he is no stranger to getting hurt. He may even joke about such things to cheer you up. It can always be worse. You’re alive and that is amazing~
--Got into a fight with a friend? Or worse someone from your past? Who did this to you. Well have you seen how Nakura is treated for stabbing shinra? If you’re important to Izaya, the person who hurt you Isn't. No power in heaven could save that person from the anger he feels for damaging you. You might not want or need that but it’ll make him feel better knowing they didn’t get to sleep easy.
--If there’s no reason to the sad, you’re just... sad. He might struggle with that, there’s less information to work with but Its not like you can’t google sadness remedies and just try those. What’s more if you are his significant other, he probably knows you well enough by now. I mean he’s an informant. He knows what you like and will surround you with it.
Some warm tea? Cocoa? Favorite foods/meals? If its simple enough he’d make it himself or have it delivered.
Do you need a blanket and cuddles? Sure but like above he may have his laptop or phone with him to keep working.
Sometimes just being close is enough and while he doesn’t require such things, he’s not ignorant to deny you that comfort once in a while. It does make work harder for him but you are important so he’ll sacrifice the productivity for a few hours to let you feel better.
Izaya’s by no means is incapable of comfort. And if you are important to him he will show it, but just not loudly. He says he can’t play favorites, but you are his favorite, and even if he won’t say it, you would know. His love is shallow at times, and his moves are reactionary based upon yours, but he would make sure you are looked after.
Hope this makes some people happy! Was fun to write!