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Keima first met Ryō during Tenri's reunion with him and despite to Nora's comments on Ryō being useless, Keima never really did interact much with him.
On the morning of August 31, Tenri decided to meet with Keima to show him a trick with a small magic box. She tries to greet him but gets too nervous, spaced out, and talked about the weather instead before Keima went back in his house.
But he never hurt her the same way with Chihiro. Chihiro looks more pitiful because she forged his way to Keima but eventually got rejected, whereas to Tenri who waits patiently. So presumably, Keima did not see Tenri's love that strong.
It was stated back when Tenri and Ayumi are talking. His tactics may be like in games but his feelings are quite genuine. Aside from that, I think, one of the reasons why Keima has a connection with Chihiro is because she's the first girl he ever hurt.
Very few people, notably only people who are very close in relation with Keima, can ever tell if Keima is lying or forcing himself to act, one such person being Tenri. Keima however, does have weaknesses that has made his capture in-real-life harder and more difficult:
When she brings them to Miyako's house, she reveals her recording of Keima talking about Ayumi's conquest, deliberately blowing up Keima's plans, but with the later reveal that she did this to help him.
Chihiro, throughout the Mercurius conquest of the Goddess arc, overloaded with the Ship Tease towards Keima to make the Love Triangle with Ayumi at the time an absolute mess; even being confirmed to be a girl like Tenri who'd liked Keima before her original conquest arc had even occurred.
People also ask
Did Tenri ever meet Keima?
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Why did Tenri ask Keima to trap her in a box?
