I think of Frank Whaley as the guy, along with Jon Cryer, who filled in the "nerd gap" created in the '80s when Michael Anthony-Hall buffed up and Robert Downey, Jr. got strung out, but that's probably not fair. Anyway, he's not in the film Like Sunday, Like Rain but he did write and direct this sweet little tale of a precocious rich boy who ends up with a beautiful young girl from the wrong side of the state as a nanny.
Eleanor leaves her loser musician boyfriend Dennis, who manages to cost her her job by having a tantrum at the restaurant where she waits tables. Penniless and homeless (she was living with Dennis) a quick call home makes it clear she's not welcome back there and not happy with her sister's new job (as a stripper, is implied).
Meanwhile, super-genius Reggie daydreams through his AP Calculus classes (he's got the material down at least as well as the teacher) and lugs his cello around between his rich kids' school and the ridiculously opulent house where his mother browbeats a bunch of Latin American women into coddling Reggie.
Mom insists, and requires the help to insist, that Reggie take the car she has constantly waiting for him, but Reggie is smarter than she is, and has arrangements with the help vis a vis getting them to go along with him.
When Eleanor replaces a suddenly absent nanny, it's not exactly love at first sight. As pretty as she is, he's not the sort of kid who would just fall head-over-heels at first sight. (Reggie's a lot like an old man, in a lot of ways.) But in their time together, where she's his sole caretaker, they have a lot of time to get to know each other.
So, yes, what we have here is basically a love story. And it's to his credit that Whaley does this effortlessly, without ever going into sleaze. (It's probably unrealistically pure, really.) Both characters are aware of their differences, and there's always a proper distance between them, such that the occasions where they do touch are especially significant. Although Reggie's friend likes to refer to her as "hot", the beautiful Eleanor is never vampy.
Reggie, especially early on, borders on unlikably smartass-y, but that's another line delicately walked by Whaley. He's smarter than just about anyone ever, a master of music, math, and many other things (though not swimming). He's right about circumventing his mother's wishes at every turn: Although largely unsympathetic, we get a little sense of what she's going through, raising this son she cannot relate to. Her misguided attempts to shoehorn him into normalcy are somewhat touching, even while terribly uninvolved and superficial.
Anyway, good little flick. Frank should be proud. Released in merely two theaters, but still ahead of Eva and Buzzard for box office.
Besides the writing and directing, the acting is quite good, being carried by Leighton Meester (Eleanor) and newcomer Julian Shatkin (Reggie). They get the chemistry just right: Eleanor can see Reggie is the kind of guy who would treat her as she deserves to be treated—to say nothing of being wealthy beyond what her destitute poor white trash mind can imagine—but never once do we see a flicker of predatoriness. She could probably exploit him, manipulate him, wrap him around her little finger and set herself up for life.
Well, maybe: Reggie is very smart, and he's aware of where he stands in a lot of ways. It is his moments of vulnerability, even though carefully controlled, that make us like him and feel for him.
Debra Messing is surprisingly dowdy and (less surprisingly) unlikable as Reggie's mom. Billie Joe Armstrong, a musician of some sort, is also really unlikable as Eleanor's musician boyfriend.
This sort of material is difficult to do well, but it's done well here. I doubt it will get a wider opening, so check it out via Netflix/Amazon/whatever..