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

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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.

20. Will & Grace Date The Same Guy — Season 9, Episode 8

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Will and Grace both take a cooking class with celebrity chef Jackson Boudreaux, and both wind up dating him — without knowing the other one is, too. The real kicker? Actor Nick Offerman, who plays Jackson, is actually married to Megan Mulally, who plays Karen, in real life.

19. Jack Meets Stuart — Season 6, Episode 13

Before Estefan, there was Stuart, Jack's original long term boyfriend. Stuart was a client of Will's who fell head over heels for Jack, and Will wound up bribing Jack to go out with him. Ultimately, the two did hit it off for real though — until Jack cheated on him, that is.

18. Grace & Leo's Impromptu Wedding ‚ Season 5, Episode 8 & 9

What starts as a pleasant day at the park turns into an actual wedding when Grace and Leo decide to take part in a mass marriage being hosted by The Today Show. Their rashness shocks everyone, including themselves, but ultimately they decide to try and give the marriage a chance, getting married (for real) again when it turns out the TV marriage was invalid.

17. Grace Gets "Spramped"— Season 1, Episode 17

Trying to take his mind off of his anniversary with Michael, Will and the rest of the gang head up to Vermont. Once there, Grace winds up rekindling a romance with a guy named Campbell, and invites him over while Jack tries to distract Will at a local gay bar.

16. Scottish Charlie Ignores Will — Season 2, Episode 15

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Will agrees to go on a date with a guy at his boss's request, and the two actually seem to hit it off. Afterward though, Charlie never calls Will, and Will stresses over what it was that went wrong.

15. The Numbing Cream — Season 10, Episode 1

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Just before his Skype date to meet Estefan's family, Jack overdoes it while applying a numbing cream to his face before a beauty treatment. The scene that follows is slapstick gold, and also pretty darn sweet, as it shows just how much he and Estefan really mean to each other.

14. The West Side Curmudgeon — Season 10, Episode 1

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While going to angrily confront Noah for his mean tweet, Grace ends up arguing with him while sitting in a booth at a diner. It's all highly reminiscent of the first time she went on a date with Nathan. It might not have been a date when she walked in, but it was by the time she left.

13. One Night Stand Diane — Season 6, Episode 2

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Although the audience doesn't see the date itself, Grace finally meets Diane — the only woman Will ever slept with — and she recounts the one night stand she had with Will. Grace goes nuts with jealousy. At first, Diane plays it cool and claims to have known Will was gay all along, before eventually confessing she's still in love with him.

12. Will Acts Like Jack — Season 10, Episode 8

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Like most of the revival, this episode is an especial treat if you've been fans of the show since the beginning. Watching Eric McCormick and Sean Hayes pretend to play one another's characters is equal parts hilarious, brilliant, and actually totally sweet.

11. Jack's Compression Garment — Season 9, Episode 2

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Obsessed with looking younger to impress a younger guy, Jack goes overboard with Karen's anti-aging devices. The compression garment he wears is so tight he interrupts his date to get Will's pruning shears to slice himself free.

10. Will Talks LGBTQ History — Season 9, Episode 2

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While Jack is busy prying himself out of Karen's compression garment, Will is dating a younger man of his own. Ben Platt guest stars as 23-year-old Blake, who shocks Will with his lack of knowledge about gay history. Blake asks, "Are we going to hook up or are you going to give me a history lesson?" Will chooses the latter.

9. Grace Keeps It In The Fam — Season 9, Episode 12

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Perhaps Grace's funniest dating blunder from the revival — or possibly all time — Grace was dating two guys, little knowing they were father and son. When she's on a date with the father, the son stops by, as does the grandfather, and it turns out she'd actually had a fling with him, too.

8. The Onion Blossom One — Season 3, Episode 14

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Who could forget Patrick Dempsey's brief recurring role as Will's love interest Matt the Sports Journalist, or the episode where they went on a date to a restaurant Jack suggested for taking guys who were still in the closet. Matt introduces Will to his boss as his brother, and Will decides to break up with Matt since he's not ready to be open. Grace is there — for the onion blossom, of course — and applauds Will's bravery.

7. Grace Dates A Felon — Season 4, Episode 14

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While visiting Stan in prison, Grace meets up with a former high school crush and starts dating him. They talk about how he use to be in a band in high school, and he says that he was actually thinking about her when he sang "Rosanna" by Toto. Unfortunately, he's two-timing her from prison, and used the exact line on another girl.

6. Grace Nearly Has A Threesome — Season 3, Episode 6

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Nicholas and Grace used to date before the start of the series. Nicholas gets back in touch with Grace to find out if she'd be interested in having a threesome with him and his wife. She considers going through with it, but chickens out at the last minute.

5. Will Falls In Love With A Dog — Season 3, Episode 18

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Will goes on a few dates with Paul, and continues to date him because he falls head over heels for Paul's dog, Pepper. Ultimately, Grace forces him to come to terms with his dog-obsession and break up with them both.

4. Jack Crushes On The Barista — Season 3, Episode 11

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Jack is so smitten with Paul, a barista at Jumpin' Java, that he goes to visit him constantly at work. He winds up with a major caffeine addiction over the course of their episode-long relationship.

3. Karen & Malcolm's First Date — Season 8, Episode 1

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It's a special moment indeed when Karen decides to get serious. Malcolm (Alec Baldwin) asks Karen out and in order to prevent her from going out with him, Will tells Karen that Stan is actually still alive. When Rosario tells Karen that it's true, Karen fires Rosario and goes on the date anyway.

2. Nathan Takes Grace To "Venice" — Season 3, Episode 21

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After leaving his clothes in her basket in the communal laundry room, Grace goes to confront Nathan in his apartment. However, he's turned his apartment into a mini Venice and prepared a surprise date for her. He pretends it's for his girlfriend "Vicki," when really it was just all just a ploy to get her to spend time with him.

1. Jack Uses Grace — Season 4, Episode 16

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Sliding into first place is the unforgettable episode that guest stars Matt Damon as Owen, a secretly straight man that pretends to be gay in order to join Jack's all-male gay choir. Jack finds out Owen's secret and aims to out him to the group by using Grace as bait.

The scene which follows isn't exactly a traditional date so much as a set up which quickly devolves into Grace and Owen getting busy on the couch and Jack ultimately getting kicked out of the choir for being intolerant.

It might have been 20 years since the first go around, but Will, Grace, Jack, and Karen are still only just figuring out how to get a handle on love. Lucky for fans though, that means there are plenty more ridiculous dates to come in future episodes.