The message that Maureen Daly conveys in the story "Sixteen" is that in affairs of the heart it is best to use your head to temper the feelings of the heart. The main character says, "My heart still prays but my mind laughs. Finally, mind wins!" "Sixteen" is a story of unrequited love. The young girl in the story feels the young man she yearns for is different; he really has feelings for her. But, he never calls, and he ends up being like so many other young men she has fallen for. “I know what the stars knew all the time—he’ll never, never call—never,” she realizes. The message is an age old one that many young people learn over and over as they grow to use reason when dealing with love as opposed to using only their feelings, which run the gamut of love and passion, to anger, and finally to reason and moving on.
Another very important message the author may be trying to communicate is that the ambiguity between true attraction and superficial flirtation often creates an emotional minefield in the arena of romance.
In the story, our unnamed narrator hopes for the young man to call. After all, he had seemed sufficiently absorbed in her at the skating rink. During their time together, the young man had been confident, attentive, and gallant. Like a professional pick-up artist, the young man had been able to make her believe that he was deeply and irreversibly attracted to her.
As time progressed, however, the protagonist had to embrace reality: "he will never, never call—never." One of the first clues that the young man was only interested in a brief flirtation with her was his immediate emotional engagement upon physical contact. He did not ask for permission to put his arm around her waist; he simply did it. Throughout his encounter with the protagonist, he set the tone for every exchange. He showed no inclination to get to know her as an individual. Our heroine concedes that she remembers nothing about the content of their conversation, only the laughter that accompanied it.
Later, the young man voiced his intention to take our heroine home; again, he did not ask for her permission to do so. His every action was calculated to project cool confidence and self-possession. Against her better judgment, the protagonist felt herself helplessly drawn to the young man. So, yes, Maureen Daly's story definitely highlights the fine line between true desire and gratuitous flirtation.