I have no doubt he loves Chihaya, and, like Bill said, he's smart, so he knows it'd be best for Chihaya to also see Arata's matches. Not to mention he needs to see them himself in order to create strategies against Arata. So, all the better if he can sit right next to Chihaya and casually touch her when they watch those matches. However, his intelligence and tactics only take him so far. He can't cope with the unexpected from someone he detests under the surface, like the high five scene demonstrated.