Rules of Engagement is the 6th episode of the fourth season and 77th overall. In this episode, all the characters are involved in one story line as opposed to pairing off in most episodes.
In the middle of having sex, Nathan inadvertently proposes to Grace. She, however finds this tacky and asks Nathan to take it off the table. Upon consulting with Will, Grace realizes that she would have said yes if Nathan had asked "the right way", so Jack, Karen and Will all help out Grace plan a dinner where Nathan can formally propose. To buy Grace time to prepare, Will takes Nathan out to a gay bar and they witness a couple get engaged.
Coming back to the apartment, Grace tries to drop hints so Nathan can propose again. She eventually kneels down and asks Nathan herself but gets surprised when he breaks up with her instead, saying everything should be easier if they are really meant to be together. After Nathan leaves, Will comes in and Grace breaks down in his arms.
- Eric McCormack (Will Truman)
- Debra Messing (Grace Adler)
- Sean Hayes (Jack McFarland)
- Megan Mullally (Karen Walker)
- Shelley Morrison (Rosario Salazar)
- Woody Harrelson (Nathan)
- Sam Pancake (Bartender)
- Jordan Feldman (Fred Homosexual)
- Dean Cameron (Guy)
- Shane Partlow (Boyfriend)
- When Will tells Grace that he had been at a gay bar with Nathan, Grace exclaims that if Nathan is gay, she is going to "have a frickin' heart attack". It has become a recurring joke that Grace is oftenly attracted to gay men and even has the ability to "turn" straight men gay, as in the case of Will and Josh.
- Sam Pancake appears as a bartender in this episode. He later appears as Jimmy, a TV executive in season 8.
- Fred (the guy who proposes at the bar) says that they will be married in Holland since The Netherlands is the only territory to recognize same-sex marriage when the episode aired in 2001. It will not be legalized in the US until 2015.
- Will implies that explaining unethical behavior to Jack and Karen is harder than doing it to Angelina Jolie and Billy Bob Thornton, who in 2001 were still married and had been known by the media for their eccentric displays of affection, including wearing vials of each other's blood around their necks.
It's a victimless crime. It's like tax evasion or public indecency. — Karen, On listening on people have sex
|Karen:||Oh, honey, I'm so excited for you. Are you nervous?|
|Grace:||A little. Are you loaded?|
It's just not how I ever imagined being proposed to, ok? I'm supposed to be holding a bouquet of wildflowers, not my own ankles! — Grace
|Grace:||I can't believe you did that...like that, while we were doing that.|
|Nathan:||Why? Was it not a happy time for both of us?|
|Grace:||It was a happy time for you. It was on the way to a happy time for me.|
What am I doing? I'd have better luck explaining ethics to Angelina and Billy Bob. — Will, Explaining it is wrong to listen to people have sex