I agree that Paulo could certainly have picked a better time to approach Lucy. However, it's true he hasn't seen her in a couple of weeks, and he's barely even talked to her on the phone. Now that he and Jasmine have broken up, he wants to jump on the opportunity to express his feelings to Lucy without further delay. I think we can all see Lucy's rejection of Paulo coming a mile away though, since she clearly needs time to regain some mental and emotional stability first, and I doubt she wants to become as dependent on him as she was on Mike.
My personal experience with high school is that nobody ends up with nobody.
As I believe I've said before, dating in high school is really more about developing interpersonal skills and finding out the types of people you like rather than finding actual true love. The latter doesn't usually happen until later on, when you're more emotionally mature.
She is probably thinking of how to deal with mike and the kiss scene.
I don't believe there is a kiss scene in the play. Sue's intention
with casting Mike and Lucy for the lead roles wasn't to get them together romantically, but just to talk and be friends again.
What we do know is that Lucy will be singing
in the play, and quite possibly wearing that dress as well. (Speaking of which, I wonder what the chances are of Paulo finding Jessica helping Lucy with her costume?
Fun fact: The school play was originally slotted to occur at the end of sophomore year (i.e. in June instead of January).