Yes, Dear (2000) : 3x23

Mr. Savitsky invites Greg to join him and his new Playmate wife, Lisa, at a charity dinner for the homeless, because he got stuck buying a table and has six seats to fill. Greg makes Kim go -- not because he wants to help the homeless, but because he wants to impress the boss and further his career by having Kim schmooze Lisa. Desperate to help him fill the other four, Greg reluctantly agrees to let Jimmy, Christine, Billy and Billy's price-memorizing supermarket clerk date, Debbie, tag along. When Greg sees Kim not doing what he asked, he orders her to go talk to Lisa, but the woman is such a foul-mouthed, lush-faced, sex-obsessed bimbo that Kim ends the conversation in disgust. After a very smashed Christine steps in and hits it off with Lisa, Greg changes tactics and decides they'll both go to Savitsky's tennis club -- via a trip that Savitsky put up for auction at the dinner -- so the four of them can spend the whole day together and Kim can win Lisa over without it looking despera