When a timid spoiled peeping tom discovers his poor law-school classmate is moonlighting as a cat burglar, she offers to set him up with the girl of his dreams in return for his silence.
It’s not clear to me: who is the main character? The voyeur or the burglar?
And it’s not clear to me what the story is about. Is her objective goal to set up him with the girl of his dreams? Is his objective goal to keep quiet about her crimes? That’s it, that’s what the plot is, that if he keeps quiet, he’ll get laid?
I find the more interesting character and throughline to be that of a female law student who resorts to burglary to pay her way through Harvard or Yale — take your pick as long as it’s one of the two most prestigious and expensive law schools in the country.
The boyfriend finding out is a side show plot thread, a complication that could set up some sort of “B” story, Odd Couple relationship. And if he’s going to be a voyeur than his penchant needs to tie into the main story thread in some way. Like, he only agrees to keep silent if he can want watch her at work, see her pull off her jobs.
As socially unacceptable as both of their behaviors may be, she is more interesting because she is proactive, taking greater risks than he is. In comparison, he’s a passive wimp.
Further to increase audience sympathy and acceptance of her crimes, i I suggest that she only targets the residences of the filthy rich. She’s a modern day, female version of Robin Hood. Could she steal not only to pay for her education, but that of other deserving poor students? And the residences of the rich are better protected (security alarms, etc.) which increase both the risk (dramatic tension) and demonstrate just how good she is — has to be.
Again, in contrast, what can be done with him to get the audience to emotionally engage with being a peeping tom?
“…timid…” implies quite and reserved, while “…spoiled…” implies entitled if not arrogant – the two descriptions don’t work together. Further, the MC is a peeping tom – really?!! And her goal is to bribe a classmate for silence with a ‘hook up’ – REALLY?!!! How is this a character the audience will want to get behind?
It also comes across as very lean on story, is this a short or full length feature?
I think you’re trying to describe far too much complexity in the logline (and possibly the story as a whole) for it to be effective. Consider simplifying the MC, as DPG wrote pick one and make him or her clearly motivated.
If it’s the peeping Tom, you would have to work mighty hard to sell him to the audience as a hero – not only is he a peeping Tom, but he also records his privacy intrusions on tape…
Not sure how you can come back from that, but assuming you still want to (you shouldn’t…), all the layers of descriptions in your explanation mean very little to the audience. Most cinema goers will recognise characters as one of three types: good, bad, and neutral. All the minutia nuances you’re trying for won’t have an effect, if anything, they’ll confuse most decision makers.
If, however, you go with the cat burglar (as DPG rightly advised) you have a morally corrupt character with a redeeming quality – doing the wrong thing for the right reason. This is actually a very powerful tendency to have in your MC – look how many Robin Hood iterations we’ve had over the years.
I myself just had a script optioned that’s about a guy doing the wrong thing for the right reason. I can’t say for sure, but I think that’s one of the reasons the producer wants the IP – it’s the kind of story that often seems to find an audience.
Anyway, this is your story so do what you think is best, but I strongly advise you rethink the concept and write a new version around the cat burglar.