Will & Grace (1998)

S1E1 The Pilot (Love & Marriage)

Grace is taken by surprise when her boyfriend proposes to her, leaving Will in a tough spot as he attempts to support her choice. However, he eventually expresses his belief that she is making a mistake, even though it jeopardizes their friendship. Things get even more complicated with the meddling of Grace's socialite assistant, Karen, along with the antics of Will's wild friend, Jack, adding to the turmoil surrounding the decision.