I think the problem with him was that he was just going along with what he thought was expected of him. His friend told him he needed a girlfriend, so he got one. He told him to meet her at the station instead of the theme park, so he did. That friend probably also told him to do whatever she wanted without question or criticism. He doesn't think for himself. When she asked for his opinion on new clothes, he didn't show any real preference. He must be afraid of offending people, or he doesn't trust his own intuition. Either way, I'm sure he and Retsuko can give it another try if he can just express himself more.