When Kate and Pete host a party, Jackie crashes and hooks up with Pete’s co-worker Sad Steve, much to Pete’s discomfort. However, when Sad Steve decides to pursue a relationship with Jackie, both Kate and Pete jump on the bandwagon to give young love a boost. Meanwhile, Hillary helps Warren and Bert put together a Gum Show live stream, and Diane faces off with Meg after she posts an unflattering picture of her on Instagram.