The 1999 episode earned two Emmy nominations — Must See TV indeed
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A version of this story originally appears in Entertainment Weekly’s Untold Stories issue, on stands now or available to buy right here. Don’t forget to subscribe for more exclusive interviews and photos, only in EW.

With season 4 of the NBC hit drawing to a close in the spring of 1998, the Friends writers decided to introduce an unexpected romantic pairing: pals Monica (Courteney Cox) and Chandler (Matthew Perry).

Marta Kauffman, co-creator, now co-creator/EP for Grace and Frankie: Our intention was not for them to be as serious as they became. One of the fun things about doing a show that has years of legs on it is that it begins to tell you what it should be. When we were shooting the scene in London where we find out that Monica and Chandler have slept together, we were in front of a live audience and the reaction was so stunning…. We didn’t expect applause to last for two minutes. We kind of went, “Huh, this is such an unexpected duo, let’s play with it for a little while.”

As Monica and Chandler’s fling deepened into something more in season 5, the friends — one by one — learned the secret, beginning with Joey (Matt LeBlanc) and then Rachel (Jennifer Aniston). But the real fun started when Phoebe (Lisa Kudrow) spied the couple together — and launched a full-on flirt assault against Chandler.

Michael Lembeck, director: The scene where she [touches his] bicep — I don’t think we ever got through it in rehearsal. Lisa was always the first one to break. She and Matthew really enjoyed this week playing off of each other. Because this particular element of sexual tension had never been there before and them discovering comedically how to go about the business of succeeding at that was, again, just a hilarious event.

After Phoebe’s overtures grew more aggressive, Monica realized the trio was playing them — and decided to play back. (“They don’t know that we know that they know.”)

Kauffman: That’s what sticks out to me, was trying to write it and see how many twists we could make without getting confused.

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With neither side backing down, Phoebe and Chandler agreed to a date. Joey helped prepare Phoebe by effortlessly popping open her top, explaining that Chandler’s “afraid of bras, can’t work ’em.”

Kauffman: We almost had to rig Matt’s fingers to make it work! [Laughs]

Lembeck: As Matt talked through what he wanted to do, it became a technical exercise: Show the costumer what you want to do and see if she can rig the dress.

Kauffman: I’m trying to remember if it was snaps or Velcro. I think we ended up using Velcro…

Phoebe’s seduction also included a trippy mating dance that was pure Kudrow choreography.

Lembeck: Lisa moves in a certain way. She is a bit rhythmically challenged, so I wanted to really take advantage of that. And all week, me, as her director, and her cast just kept encouraging her to do more because we found it so damn funny. And you can see Matthew’s little grin. There’s a moment when his head goes back when she starts doing it. If you keep your eye on him, you can see the twinkle. You can see Matthew — while Chandler is curious, Matthew is enjoying.

The scene culminated in one of the most awkward small-screen kisses on record. Chandler finally pulled away, declaring his love for Monica.

Lembeck: I remember the incredible charge that went through the audience when he said, “I’m in love with Monica.” It was electric.

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