While Sharon is at camp, Alden proves to be less than poetic or frequent in his letter writing - causing Sharon to worry that he is waning in his commitment to her as a boyfriend. When a new CIT, Jason, appears on the scene, both Maria and Sharon find themselves very attracted to him. Sharon wrestles with conflicting feelings about Alden while Maria considers Sharon's interest in Jason unfair. She encourages Sharon to seal her relationship with Alden in an effort to secure Jason for herself. However, when Jason accidentally causes Sharon to break a band on her braces, their subsequent trip to the dentist gives them opportunity to bond even further. Alden is left in the dust. A sailing regatta finally shows Sharon Jason's true colours and she realizes that Alden is indeed the guy for her.
Alden: (sings sadly and plays his guitar) Does she love another or think of me like a brother? (sighs)
Brock: You should just phone her, man. I'll even dial the camp for you, save us both from this misery.
Alden: (continues singing) Is she over me and into him? Should I sink or should I swim? (stops) Aw, man...
Sharon: (while she and Jason are in the middle of a severe storm) I thought you were an excellent sailor!
Jason: I am--in calm weather.
Sharon: (suspiciously) Anything else I should know about you?