Human relationships interweave and consequently so do romantic relationships, which can create a whole mess of emotion. I have observed, through reading of Shakespeare's Twelfth Night and volunteering at Patterson, that Duke Orsino's behavior can be equated to that of a teenaged boy.
Both the duke and a couple of high school aged boys utilize a "wingman" to hit on girls for them. Duke Orsino is so in love with Olivia, but he can't get his butt down to her house to tell her himself. Instead, he's been sending his new servant Viola, who is dressed up like a young lad to woo his fair lady. To make matters even worse, Olivia has been mourning the loss of her brother and refuses to open up to the possibility of a romantic relationship. The Duke is persistent however, and makes such a valiant effort to have his servants pour their hearts out to her on behalf of him. I really never understood why guys will have their friends hit on girls for them. Seriously when does this ever work? Personally I am turned off by the idea of a wingman, and perhaps Olivia is also.
Many a time, we can fall in love with the idea of someone rather than the person themselves. As I walked down the purple and sea foam green hallways (interesting color palette I know) of the high school, I'll often see young couples holding hands or kissing or girls giggling behind their lockers at some cute boy. This is all typical high school behavior, but I realized that we never truly grow out of these feelings. Yes, we may control them better but even as we get older, that same giddiness will return if we see an old celebrity crush on TV or begin a new romantic relationship. The Duke really is convinced that he loves Olivia, and her playing hard to get only intensifies his desires. However, the Duke barely knows her past her physical appearance. We can never fully love a person without knowing the whole being, and growing to love the little quirks about them. Shakespeare's sonnet "My Mistresses Eyes Are Nothing Like the Sun" demonstrates this idea pretty well. This play so far seems to deal with the superficiality of infatuation, as opposed to the genuine feelings in his sonnet.
Directness can prevent the complexities and love triangles that are often a product resulting from having many parties involved. If the Duke simply went to Olivia himself, perhaps he would have made a better impression on her. Now there is a whole new mess as Olivia begins to have affection towards Viola, and Viola starts to get the feels for the Duke. All the deception involved creates a complicated situation and I am interested to see how this all plays out...