"Kissing Jessica Stein" has early 2000s humour and starts off with a seemingly familiar rom-com trope involving a beautiful yet lonely career-driven woman in New York City who's in search of her Prince Charming. But when Jessica develops a friendship with Helen Cooper, an "it girl" of her time with a job at a hip art studio, she realises she may have been limiting her outlook on love, and perhaps it's time to explore a little more. This rom-com has an unexpected ending, but watching Jessica in her fullest expression of herself at the film's end is something that's really beautiful.