It's great that he can relax properly in dreams, but I'm with Lily on this one. It's not healthy to avoid new situations just because they're uncomfortable.
Kuroki is stuck in a socially awkward rut and he needs to start making an effort to get out of it. Connect with people, experience things, that sort of thing. The overbearing job definitely doesn't help the situation.
Also, Lily...you know you could probably get him to take you on a dream date if you just made the request?