Will & Grace (1998)

S3E18 Mad Dogs and Average Men

Grace can't help but be captivated by Sumner, Karen's attractive and charismatic nephew. However, her efforts to set up a date are repeatedly sabotaged by Karen, who spins an elaborate web of falsehoods to keep them apart. In the meantime, Will finds himself wanting to end his unfulfilling relationship with a clingy, awkward guy, but he keeps delaying the inevitable break-up because he's become so attached to the adorable dog, Pepper, that belongs to his partner.