Will & Grace: Original
It's the Gay Pumpkin, Charlie Brown
S5 E5:
On Halloween, Grace (Debra Messing) allows her new beau Leo (guest star Harry Connick Jr.) to drag her into the rustic fall countryside for a long and scary bike ride - along with a reluctant Will (Eric McCormack) and his newfound friend (guest star Jason Marsden) - but she finds that she can't pretend to be the outdoorsy type just to please her man. Meanwhile, Jack (Sean Hayes) coaxes Karen (Megan Mullally) into attending a gay men's therapy session when she feels slight - very slight - pangs of marital guilt over her earlier attraction to the courtly suitor Lionel.
Starring
Reginald Veljohnson, Harry Connick Jr., Jason Marsden