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Originally Posted by The Green One
He doesn't actually think Rias would kill him....well no more then he expects any girl to for normal anime pervy shenanigans. He just ends up second guessing every signal and sign of affection getting sent his way because he just can't believe she's being serious due to the trauma he suffered. He just keeps thinking that Rias is "spoiling" her servant even if that makes no sense to anyone else looking at the situation.
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The Green One, when you think about his second guessing every signal and sign of affection is to be expected when you stop to consider all the things that Rias did to him before she took a romantic interest in him. Many of the things she is doing now are very similar to the things she did before she took a romantic interest.
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Originally Posted by GDB
Keep in mind, before Rias even decided to make Issei her's, she had basically tried to pair him and Asia together. She told him that Asia was his responsibility and to look after her, and then put her in his house. All this knowing that they already had some level of feelings for each other.
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Very true, Rias was more than aware of Asia's feelings for Issei early on. She even noted that Asia was jealous, when she saw Rias giving Issei a kiss on his forehead. She even had them do errands together or have Asia assist Issei with his devil job. She tired to help Asia make progress and develop her relationship with Issei even further by giving them enough time alone together.