Who's the boss?: How the workplace will-they/won't-they became a TV staple

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https://www.avclub.com/how-the-workp...me-a-tv-staple

Who’s The Boss? (a.k.a. the employer-employee subset of will-they/won’t-they)

On television, a workplace romance tends to go one of two ways: Either two coworkers or partners of (relatively) equal standing get together or the employer and employee (or supervisor and supervisee) do the same. In the case of the latter, especially in sitcoms, there’s a bit of an idealized version of the power dynamic at play, usually with the “inferior” character ironically having the upper hand over the “superior.” (Though the optics of the two getting together can come into play as a roadblock of this particular type of will-they/won’t-they story.) In fact, there was a whole series titled after the question posed by this particular take on the will-they/won’t-they trope: Who’s The Boss?

Who’s The Boss? (8 seasons, 1984-1992)



And here is the titular example for this piece. So, was the boss Angela (Judith Light), the Connecticut advertising executive who’d figured out how to balance work and family as a divorced single mother making it in the 1980s? Or was it Tony (Tony Danza), the alpha male retired baseball player and widower that Angela reluctantly hired as her live-in housekeeper? (Spoiler alert: According to Community, the answer was, in fact, Angela.) Could they ever make it work, both professionally and romantically?

Though it’s one of the quintessential examples of this type of will-they/won’t-they relationship, Who’s The Boss? demonstrated the problems of waiting too long to answer things in the form of “they will.” Angela and Tony didn’t get together until the eighth and final season—and only did so to prevent the series from being canceled after its seventh round, though the move ultimately failed to boost ratings. The series concluded with a three-part episode (“Savor The Veal”) that saw Tony and Angela try and fail to make a long-distance relationship work, only for Angela to then try and fail to put Tony’s happiness and new dream job in Iowa first, then for Tony to give up said dream job and return to Connecticut to be with Angela, promising to look for other work in the area. The two got engaged in this final season, but apparently, the wedding never occurred as a promise originally made by the producers. And it’s not the last time long-term promises being kept (or broken) affected the outcome of a will-they/won’t-they.

In June 2022, the streaming service formerly known as Freevee (so, Prime Video) announced a Who’s The Boss? sequel series—as Melissa & Joey, perhaps, didn’t fully scratch that itch—with Danza and Alyssa Milano (as the potential “boss”) returning. However, in October 2024, Amazon officially killed that potential comeback. But the original Who’s The Boss?’s real legacy, outside of its former Nick At Nite and TV Land prominence, is as a template for the troubles of drawing out the will-they/won’t-they instead of striking while the iron is hot.