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When he met Tanjirou and Nezuko he thought about a lot of things; he worried about them and prayed they could survive in a world full of demons... He prayed Tanjirou could get what he wanted and find a cure for his little sister.
He also took care of them as his own children, despite knowing it was not a good idea to get attached.
Now Tanjirou sends him letters regularly and visits him every now and then. Urokodaki is proud; the boy has proven he can take care of himself and his sister Nezuko.
He's really happy for them.
However, he certainly didn't expect all the hashira to pay a couple of visits to him. They usually come when Tanjirou is there, but it's not all of them at once.
And Urokodaki has noticed their true intentions, of course he has, it's not like they're trying to be subtle, but unfortunately for them Tanjirou is on another level of obliviousness when it comes to those things.
He's not going to deny it amuses him and he's glad he's constantly wearing his mask around them.
Now, he must admit that sometimes it irritates him as well; Tanjirou is like his son now and of course Urokodaki wants nothing but the best for him. The Pillars are the best swordsmen alive and they have saved thousands of innocent people, but that doesn't make them a good match for Tanjirou.
However, it seems they recognize how important Urokodaki is to Tanjirou, because after a couple of months, they ask for Urokodaki's blessing to start formally courting Tanjirou.
He doesn't make it easy for them at first; he knows it'll be Tanjirou's choice in the end, but that doesn't mean he's not going to give a little bit of advantage to the ones he thinks are best for Tanjirou.
Of course Giyuu is the first one to get his approval; Urokodaki even wishes him good luck because Tanjirou is extremely oblivious and Giyuu can be really shy and insecure sometimes.
Shinobu wins him over easily; she gets to the point and tells him everything she can give Tanjirou and how she'll take care of him. Urokodaki is more than impressed.
Now, Mitsuri is the other one who gets permission to start courting the sunshine, Urokodaki tries not to chuckle at the nickname because he must admit it suits Tanjirou really well.
Mitsuri is so sweet and charming she even convinces Urokodaki to give Obanai a chance as well which he eventually, although a little bit reluctantly, does.
Tengen doesn't get his approval the first time.
"You're married already."
"My wives love him too," Tengen assures him, which, to be honest, surprises Urokodaki. Usually when things like that happen, someone ends up getting jealous and hurt. But it seems the sound hashira is being completely honest.
"Come back in a few weeks if you're serious about him, then you can ask me again."
Sanemi doesn't even get the chance to explain himself, he gets a firm 'No'. Urokodaki knows everything that happened during Nezuko's trial and he's not sure he trusts him after he stabbed Nezuko and tried to hurt Tanjirou too.
What makes him hesitate for a moment is the devastated smell that reaches his nose as Sanemi leaves his house after saying goodbye to Tanjirou.
Urokodaki is not sure about Kyojuro, he's too intense; he's constantly invading Tanjirou's personal space, although to be fair the boy doesn't seem to mind. However, Urokodaki has seen Shinjuro lately and he's not sure he wants Tanjirou to become part of that family.
Kyojuro promises to come back and keep doing his best to earn Urokodaki's approval which makes him win a lot of good points.
"Aren't you too young for this?" Urokodaki asks Muichiro as soon as the boy says he wants to talk to him.
"I'm only one year younger than Tanjirou."
Urokodaki promises him to think about it at least. When he sees Gyomei, he doesn't even roll his eyes but wonders what exactly Tanjirou did in order to have all the hashira wrapped around his pinky like that.
It doesn't take Gyomei a lot to convince Urokodaki; he's the strongest Pillar and yet he's always been kind and gentle with Tanjirou. Urokodaki knows that if the boy chooses him he'll be in good hands.
After a while and watching how everyone treats and looks at Tanjirou, Urokodaki gives in and allows Tengen, Kyojuro, Muichiro and even Sanemi (after finding out he actually apologized to Tanjirou and Nezuko) to court the boy.
Besides, he knows it'll take a while for something to actually happen because no matter how blunt all the Pillars are, Tanjirou is unbelievable oblivious.
Sometimes it amuses him watching them all together, trying to draw Tanjirou's attention and even growling at each other for it. Because even if they have his blessing now that doesn't mean Urokodaki is going to help them.
That's something they have to win on their own.