Eric McCormack and Debra Messing both selected this two-part episode as their tapes for Emmy consideration for this season. McCormack won, but Messing lost to Patricia Heaton.
Originally aired as a one hour Thanksgiving Special episode, though syndication will usually air them in two half hour episodes. NBC counts this as one episode, as they will with any W&G episodes that air as a one hour episode. This may also include Super-Sized (40 minute episodes). The regular part of the episode was filmed on November 6th, while the flashbacks were filmed two days later. You can see the entire episode as it was meant to be seen ont he Season 3 DVD.
Will: No, no, no, no. Listen. That's not what I'm saying. I don't think I really knew for sure until we were in bed together. You know? And I took one look at you in your sexy underwear, and I just went... "Whoa. I am gay." You know? I mean, do you know what I mean?
Grace: Yeah. Yeah, I think I do.
Grace: Just--just one thing. (Pinches Will's Ear)
Will: Ow! Hey! Hey! What are you doing? What are you doing? What are you doing?
Grace: You bastard! I'm in love with you, and you're treating me like some sort of test drive?! You take me out for a spin, and you go, "Hmm, I don't really like the feel of this one. I think I'd rather have a stick."
Bobbi: What's wrong?
Grace: (Crying) Will's gay!
Bobbi: Oh, Julius, I owe you twenty bucks!
Joyce: What's wrong?
Bobbi: Will's gay.
Joyce: Aw, Grace you ruin everything!
In the flashback, Will ducks to hide from the one and only woman he had sex with. She has short red hair and wears glasses. In Season 6, "Last Ex To Brooklyn" we actually meet Will's "one and only" and she has long blonde hair and no glasses.
If Will was shopping with Jack when he ran into Grace, why didn't Will leave with Jack?
If you look hard, you'll notice the fadeup sequence from when Will and Grace walk off to where "younger" Will and Grace are standing and waiting for the cue to move.
In the scene in which Will is sitting in Bobbie Adler's bathroom, talking to Jack on the telephone, the shots alternate between the bathroom and Jack's bedroom. At the beginning of their conversation, the digital clock in Jack's bedroom reads 12:07. For the next few shots, each time the audience is taken back to Jack's bedroom, the time on the clock has changed according to the actual time lapsing in the scene. However, in the middle of this sequence, the digital clock suddenly reads 12:24, where it had read 12:09 in the shot immediately preceding. Finally, in the very next shot in Jack's bedroom, the clock has gone back to "real time," with a reading of 12:10. The assumption is that the shot in the middle of this sequence had to be re-done, thus reflecting the time passage on the clock.
When Will & Grace are walking along the street in the rain, several cabs stop by to offer them rides. Anyone who lives in Manhattan knows that you can't get a taxi in the rain, much less one to solicit you.