I'll be totally upfront and say I only watched this because David Hewlett's in it. He actually had a larger role that I expected, plus his sister Kate is in a couple of scenes, and his wife, Jane Loughman, is a producer.
It's a rom-com featuring an aspiring screenwriter, Cole, who views the real world as a trial run for his script ideas in which he loathes tropes and cliches, and we see some of it play out onscreen almost as alternate scenes of soft lit images with lens flare. He's Not Like the Other Screenwriters (he totally is). Pretty much a loner except for one friend who also aspires to be a screenwriter, and the original plan was for the two of them to go to Hollywood to try to get a break there.
Then Cole thinks he's found a shortcut when he meets the daughter of his screenwriting idol (David Hewlett). He's more than a bit of a stalker, trying to orchestrate a "meet cute" with Haley, with the plan to write the script for her to be into him enough so he can be around her dad and get him to read his actual script. It actually works a bit too well, and he has to improvise his too well-scripted ideas and figure out how to deal with living in the moment.
The film is also very meta, with most of the characters being some level of unlikable (especially Cole), and one of the bits of feedback he finally gets on his script is he should have some likable characters. I'm sure someone more into screenwriting and film studies would get even more out of the meta.
Another bit of that meta is giving it a Hollywood ending... but is it really? It's one of those films you can interpret the ending how you want, if you're so inclined. It's a little too up it's own ass, much like Cole.
[Spoiler (click to open)]I don't normally give big spoilers, but I wanted to say there's an LGBT element to the film that's not obvious at the start. Watch the trailer closely and you'll probably see it. It also creates a love triangle, sorta, and that's the bit left to your interpretation at the end. It was very obvious about halfway through that Cole is bi (or I was hallucinating), but it's not as explored as his relationship with Haley and her father. I do wish the film had given a real resolution instead of just heavily hinting about it, because it's such a small part of the film, I have yet to read a review of the film that even mentions it. We're getting more queer happy endings, and this stopped just short of one. But I'm used to creating my own Happily Ever Afters. [shrug]