Some Workplace Crushes Make You Want To Clock In On Your Day Off. Winnie Chambers finds herself three months deep into a job she despises at a company she adores. Enduring a boss who oscillates between passive aggressive and outright rude, she feels more like a glorified errand runner than the executive assistant she was hired to be. Her only solace lies in her interactions with the fine IT guy, who she relies on to help with her perpetually malfunctioning laptop. Jamaal Singleton's workdays follow a routine: staff meeting at ten, lunch with his work bestie, Risha at noon, and afternoons spent in his cubicle finishing up projects. But since Winnie Chambers arrived, Jamaal's predictable work routine has been turned on its head. He now spends his days hoping she encounters an IT issue that requires his assistance, strategically wandering the office for a chance to catch a glimpse of her. He fantasizes about her smiling in his direction or confessing her feelings for him on a random Tuesday. At night, Jamaal finds himself drafting list of pros and cons about asking Winnie out on a date and the likelihood of success. Both Winnie and Jamaal arrive at work each day with the same thought in mind ... a chance encounter in the elevators that leads to locked eyes and a passionate make-out session between the second and eighth floors. While they navigate their careers, they also must grapple with how to win over the other's heart.