My Job Description Somehow Includes 'Marry the Boss'— Episode 50

Gwen Jewell works part-time to fund her father's prosthetic surgery and accidentally humiliates CEO Jim Hunt at a banquet, sparking an awkward feud. They meet again at a bar and unexpectedly spend the night together. Gwen later becomes his secretary, and amid workplace conflicts and a surprise pregnancy, Jim proposes. With that, they enter a marriage of convenience.