'That Moment When' is a series that delights in leaving its viewers covering their eyes and begging for respite — not because of gore or terror, but because of how awkward the situations get. The series follows moments from the life of Jill, "a hot mess" who constantly finds herself bumbling through brutally awkward conversations.
The series differs from cringe comedies of the past by taking advantage of its digital nativity. 'That Moment When' pulls viewers even deeper into the discomfort by creating moments for interactivity. For example, one scenario shows Jill desperately trying to remember how she knows someone she meets at a party, and viewers get the chance to click at the hints that she notices throughout her interaction. Though the scenes change depending on the option selected, they aren't likely to end up on a comfortable path.