After listening to Grayfia's introduction, Dante asks her, "So, Miss Grayfia, where is everyone?" Grayfia looks at Dante and responds, "Miss Rias said everyone was tired, so they left early. Then she told me I should take you to a place where you can sleep." Dante listens to what Grayfia says and replies, "Alright then, lead the way, Miss Grayfia." Grayfia nods and begins to guide him out of the academy until they reach a simple house.
Dante looks at it and jokes, "Well, the palace doesn't have luxuries, but it's not bad." Grayfia says, "Thank you for the compliment; now, let's go inside." Dante follows her in and then says, "What do you mean, compliment? Is something wrong, Miss Grayfia?" Grayfia responds, "Well, I live here while I'm in the human world." Dante asks, "Miss Grayfia, are you still single?" Grayfia looks at him and says, "Well, yes, why?" Dante looks at her and says, "Well, I thought maybe you were dating someone from the Gremory household since you're helping Rias." Grayfia replies, "Well, I actually help all the demon kings in the demon world; I just enjoy spending a bit more time with the Gremory household, as I get along quite well with Miss Rias."
Dante, thinking and joking, says, "So, Miss Grayfia, would you go out with me?" Grayfia looks at him, turns around, and continues walking until they reach the living room, where she says, "Mr. Dante, I appreciate that you find me attractive, but I don't want anything at the moment. This is where you can sleep; there's a sofa available." Dante looks at the sofa, lies down on it, and says, "Well, I never thought I'd have a throne to sleep on, so I'll settle for this." Grayfia, after seeing him on the sofa, goes to her room.
Well, it seems some things have changed, though not too much. First, Grayfia didn't marry Rias's brother, and I think Issei was even more hurt by Yuuma's betrayal, but I suppose that doesn't matter much. We should train and see how far these kids can go, Dante thinks.
Dante sleeps, and the next day, he wakes up to see Grayfia preparing breakfast. Dante approaches her and says, "Good morning, Grayfia. You know, I have pizza to eat, so there's no need to prepare my part." Grayfia says, "I think it's better to have a healthy breakfast, Mr. Dante." Dante jokes, saying, "It's not necessary to take things so seriously." After a while, Dante starts walking toward Kuoh Academy but stops by another place first.
Dante, now with Issei, decides to go to the Occult Club's room. Dante knocks on the door and enters, saying, "Rias, look what I found on my way yesterday." Rias sees Dante and says, "Issei Hyoudou, what happened for Dante to bring you here?" Issei looks at Rias and explains what happened to him the day before. After listening to the story, Rias asks Dante, "So, what do you want me to do with Issei?" Dante looks at her and jokes, "It's not right to leave a wounded dog, right? You need more help, and Issei could use a little protection and training. I think both of you can come to an agreement." Rias observes him and then looks at Issei, saying, "Issei, in short, we are demons, and for me to help you, you'll have to become my servant." Rias explains how she will help him if he agrees to transform into her demon servant.
After hearing Rias's explanation, Issei looks at her and asks, "So, is Dante your servant?" Before Rias can respond, Dante says, "Kid, I'm not even a pure demon; besides, I'll be helping out for a while, so you should try to get along with your future teammates." Rias continues, "As Dante said, he'll be helping us for a while, but then he'll leave. I hope we can get along." Issei looks at her and replies, "Alright, just make sure they don't open my stomach again."
Some time later, in a place where no one would disturb them, everyone gathers, this time with Issei. Dante starts speaking and says, "Well, we'll do the same as yesterday, but first, practice among yourselves. There are four of you, so pair up. I'll be training with Issei." After everyone picks a partner, Dante and Issei stand facing each other. Dante says, "You know, kid, you won't really improve much until you awaken your Sacred Gear, but I don't think it's a good idea to force it, either." Issei asks, "Why? Wouldn't it be better to awaken it quickly?" Dante responds, "Well, there are ways to do it. First, you can awaken it by training, and someday it'll just happen; second, if your life is in danger, it should activate. But as we saw, you almost died, and it didn't. I know a way to make it happen, but, let's just say, you'd need another hole in your stomach." Issei looks at Dante and says, "Well, let's train; I don't want another hole just yet." Dante looks at him and says, "Alright, let's start. This is easy: you come at me with everything, and then, when you're tired, rest up, and we'll repeat the process." Issei replies, "Alright."
After training together until nightfall, Rias gathers her group and says, "Alright, everyone, continue with your work, and Issei, remember that now, as a demon, you'll need to make contracts with humans as part of your job. It shouldn't be difficult at first." Issei responds, "Alright, President." Dante watches as everyone leaves and, left alone with Rias, comments, "What do you think? Aren't they improving? Quite a bit, though each one still has an issue." Rias looks at Dante and says, "Well, each has their own story; maybe they can solve it in the future." Dante says, "You know, strength comes with how you want to use it. If they have the strength but can't wield it, there's no point in them becoming strong." Rias replies, "I'll see if I can do something."
After this, they repeat the training for several days, until one afternoon, Dante goes out for a walk.