Sort of a Chicago Love Story

Think “Nick & Norah’s Infinite Playlist” meets “Reality Bites," a blend of breezy romantic exploration and quirky comedic charm, all steeped in the gritty yet romantic essence of Chicago.

Sort of a Chicago Love Story is a witty and heartfelt romantic dramedy that follows Grace Dalton, a posh British expat, and Riggs Cole, a rugged Chicagoan comedian, whose lives intersect in unexpected ways over the years. What starts as a chance meeting on the eve of graduation at the University of Wisconsin blossoms into a chemistry-laden, fleeting night that neither of them forgets. Five years later, Grace’s fast-paced corporate career brings her to Chicago, where she reunites with Riggs by chance at his bar.

As Grace grapples with career uncertainties and the looming threat of deportation, Riggs is trying to make his comedic dreams a reality while navigating a past haunted by family struggles and neighborhood pitfalls. Together, they explore Chicago, reconnecting over shared laughs, pizza debates, and their contrasting but complementary worldviews. Their relationship, defined by humor, sincerity, and serendipity, highlights the challenges of balancing personal aspirations with emotional vulnerability.

Set against the vibrant backdrop of Chicago’s jazz bars, pizza joints, and cultural quirks, this story blends sharp humor with tender moments, proving that love can find you even when you're not looking for it—if only you’re willing to embrace the mess.