He gains access to the set of her current film by contributing to that movies crowdfunding campaign.
Jillette himself is happy to admit this is not your average boy-meets-girl tale.
Well, I wrote a crazy movie, just an insane movie, he says.

Credit: Dread Central Presents
I wrote a movie that was too weird for anybody.
I put it on the shelf as a very strange exercise.
I loved the idea and I loved the way I saw the movie in my head.
But I put it aside completely until someone recommended to me that I see a movie calledLookby Adam Rifkin.
I saw the movie and thought it was the greatest movie of the 21st century.
I couldnt believe how good it was.
I saw it on a Friday night, about midnight, went to Facebook, and at 1 a.m.
I wrote to Adam Rifkin and introduced myself.
At 4 a.m. we had decided to do it.
To finance the film, Jillette and Rifkin launched acrowdfunding campaign, ultimately raising over $1.1 million.
If we can get money from 5,000 people, and like 5,000 people, weve done it perfectly.'
Rifkin admits that attracting actors to the project was a challenge.
And then, once people had signed on, everybody was a total sport and rolled with the punches.
You know, there were many times when it was very confusing shooting the movie.
Is this the movie within the movie?
Is this the movie that Penn is shooting?
How does this fit together?
I mean, even Penn was getting confused at some point and hewroteit.
But everybody was just game and thats what made it super fun to me.
The film gave me the chance to direct two movies in one.
It was a real fun exercise, getting to explore both styles of filmmaking in one movie.
We made exactly the movie we wanted to make.
We did the Slamdance Festival and it did really well and it played a few other places.
But finally a company came to us that loves the movie and wants to put it out.
Its a very, very weird film and has scared off distributors from day one, says Rifkin.
They are not at all afraid of how hard of a movie this is to sell.
So, more power to them for rolling the dice and taking on our crazy little film.