It's the Gay Pumpkin, Charlie Brown is the 5th episode of the fifth season and 103rd overall.
A bicycling adventure tests Will and Grace while up in the Catskills with Leo and his pal in a quest for Halloween pumpkins.
Gay Group Therapy
Jack notices that Karen is still bothered by the guilt of almost having an affair with Lionel Banks so he takes her to his gay group therapy for help. There, Karen decides to admit everything to Stan.
However, upon entering Stan's bedroom, she catches him having sex with another woman. She later tells Jack that she has left him.
A Pocket Gay
Will and Grace, who hate doing outdoorsy activities inadvertently agree to go pumpkin picking at the Catskills with Leo for Halloween. Leo brings along his friend Kim for Will, who turns out to be at least 7 inches shorter than Will. Jack refers to him as "pocket gay", the perfect "travel-size" homosexual.
During the trip, Will begins to resent everything and crashes his bike. He is taken to the cabin where he and Kim bond. Grace continues on with Leo and a resolved taste for adventure. Soon enough, she breaks down and admits to Leo how much she hates the outdoors. As rain poured over the pumpkin patch, they share a kiss.
- Eric McCormack (Will Truman)
- Debra Messing (Grace Adler)
- Sean Hayes (Jack McFarland)
- Megan Mullally (Karen Walker)
- Harry Connick Jr. (Leo Markus)
- Jason Marsden (Kim)
- Reginald VelJohnson (Dr. Kaplan)
- Olivia Kohan (Trick-or-Treater, uncredited)
- Bianca Morris (Trick-or-Treater, uncredited)
- Karen reveals that Stan likes to play "Tell Me Something Good" by Rufus (featuring Chaka Khan) when they make love. This is the same song playing in the outro when Will sneaks Kim into his apartment.
- This episode features the first appearance of Café Jacques', a table with two chairs set up outside Jack's apartment where visitors can dine "al fesco."
- Olivia Kohan and Bianca Morris were uncredited as the trick-or-treaters. Olivia is co-creator David Kohan's daughter. Bianca is the daughter of assistant editor Todd Morris.
- Title is a play on the Peanuts Halloween special It's the Great Pumpkin, Charlie Brown.
- While wearing his yellow biking helmet, Will likens himself to The Man with the Yellow Hat character from the Curious George children's books.
- Grace resolves to be like "the girls on Little House on the Prairie but with makeup and sight", referring to the character Mary Ingalls from the series, who lost her sight at age 14.
- While trying to remove a stain on her suit, Karen dramatically exclaims "out! out, damned spot!", Lady Macbeth's famous line from the Shakespearean play.
From here on, it's a new Grace. And new Grace is gonna be adventurous and outdoorsy. Like the girls on "Little House on the Prairie," but with makeup and sight. — Grace
At least now we get to go home, get away from all this fresh air and scenery, and spend Halloween like civilized people: getting hammered in a crowded bar. — Will
|Grace:||God, Kim's like a machine.|
|Will:||Or a wind-up toy.|
I feel a little bit uncomfortable. All of these gay eyes on me. Judging me. Undressing me. Then dressing me up again in a different outfit. — Karen, in gay group therapy
No. No more of your damn gay group therapy. How many times you expect me to sit through "Mamma Mia"? — Karen
I used to have multiple personalities. Now I'm only dating one guy. — Jack
|Jack:||Well, you see what you have there, don't you?|
|Will:||I see what I don't have, the other half of my date.|
|Jack:||What you have... is a pocket gay.|
|Will:||A pocket gay?|
|Jack:||A pocket gay. The perfect travel-size homosexual. Just pop him in a man-purse, a briefcase, and you're good to go. In ten years they'll be making 'em all that way.|