S4, E13: While buying holiday gifts, Grace (Debra Messing) schemes to fix up the giggling mistress (guest star Lesley Ann Warren, "Victor/Victoria") of Will's (Eric McCormack) father with a friend as a favor to Will in hopes that she will abandon his old man - but the scheme dreadfully backfires when they are forced to press a gay friend (guest star Tim Bagley) into service as a date at the last minute. Meanwhile, Jack (Sean Hayes) and Karen (Megan Mullally) have no horse sense when they buy a nag for breeding and expect a financial windfall.