20 Dates From 'Will & Grace' That Are So Outrageous, It's Hard To Believe They Didn't Give Up


The main love story at the heart of Will & Grace is the one that takes place between Will, Grace, Jack, and Karen, but that doesn't mean that the four of them haven't dabbled in some pretty unforgettable dating exploits on the side. When the show first premiered in 1998, it was often hailed for its portrayal of two men casually dating in New York City, which was still uncommon to see on network television. Now in its revival 20 years later, the show still strives to show modern dating in a way that's topical, fresh, and just a little over the top. Below are 20 of the most outrageous dates from Will & Grace, over the course of the show's ten seasons.

Star-studded, sidesplitting, serious, or utterly silly, the following selections show the whole breadth of entertaining dating scenes that Will & Grace has to offer. In addition to the fab four, this list also boasts guest stars like Patrick Dempsey, Nick Offerman, Alec Baldwin, and Matt Damon. Starting with the mildly amusing and working up to the most outrageous and unforgettable, Will & Grace just wouldn't have been the same without this motley assortment of romantic misadventures and mishaps.