correct me if I'm wrong, but I think nacchallenge ka lang kay no.1 kasi insensitive sya, you might need some adventure with him na it will be satisfied for you kung mapagbago mo sya at mapansin ka. then for no. 2, you have a feeling for him already, pinipigilan mo lang kasi challenging si no.1.
to answer the question, kay no. 2 kna lang, it will not be hard for you naman kasi you already have a feelings for him. give him a chance and focus on him. remember, love is not only a feeling, its a decision.