This is one of those independent films made with a love and care that just grabs your heart and sucks you in. In this case, it is also a real Chicago production. While I have no involvement, I know some of the names in the credits and a bit of their backgrounds, and I can infer -- or imagine -- from that how this production came together.
I don't think I can give enough credit to Aubrey Dollar. She takes her character, inhabits her, and makes you fall in love with her. I can see how Josh ends up where he does. And while his character is more laid back, there are moments where the film really shows their chemistry to best effect. And like the best such scenes, it's the small things, the momentary interactions and rapport, that make this.
Add to this supporting cast who can shine and paint a convincing character, not just a foil. Spence is particularly good at this, as Molly's sister-in-law. And Josh's "hook up" interest, contrary to where stereotype might take such a character, proves herself to be surprisingly and refreshingly sympathetic.
No, not everything is perfect. This is still a smaller, independent production. And it has a few quirks. Ones that, if you like the film, can actually be kind of endearing. But it works very well in the essentials, including script, timing -- kudos again to the actors, as well as the editors -- cinematography, and editing. And the music! (Including some that is definitely local; you wouldn't know about it, otherwise.)
As others have commented, this is a film I find myself watching repeatedly. It never fails to lift my spirits -- and wish for my own Molly, fire and all, especially the heart and humor.
It's become sort of my personal contemporary independent Chicago film exemplar. Something I stumbled across and came to own as such. I found another one that is similar for me, for New York: "Alto". These little slices, well done and with a lot of heart, that are like a personal souvenir one holds on to as a reminder of a place and time that's special to them.
Oh, and I almost forgot to mention: This film carries some of that sentiment, itself. For example, the references to John Hughes and his films set in Chicagoland, that captured a time and adolescence for a generation that has now gone on to reflect upon our time and place. While remembering that heart.
(I'll add that, perhaps less noticed, the exterior of the frame shop is a building that IIRC is just west of the house that was the exterior of John Candy's home in "Only the Lonely", a film on which Hughes was a producer. And Candy starred in his earlier "Uncle Buck".)