Vanessa, hoping to finally win her difficult activist mother Gabriela's approval, desperately vies with Blair for the honor of delivering the freshman toast at NYU. Meanwhile, Dan invites Olivia to meet Rufus and Lily, which leads to all sorts of problems for the new couple. Elsewhere, Serena and Nate team up to help Carter win money at a poker table to free him from his arrangement with the Buckleys; but Nate has a different plan in mind.