MacKenzie walks up and asks Sloan why Will is talking to Nina Howard, TMI magazine's gossip columnist. "Oh, he shouldn't be talking to her," Sloan says, then downs the rest of her champagne. When Olivia Munn is the best thing about your TV show, you know you have a bad TV show. I really thought she would be the worst thing about this show. I'm still amazed that it's the opposite.
MacKenzie rushes over to take Will away from Nina and warn him about her. Will doesn't think he has anything to worry about: "She writes features," he says. MacKenzie says TMI is the kind of magazine that puts Jennifer Aniston on the cover every issue. Are we still doing that? Were we all the way back in 2010? Probably. I still can't figure out why. I don't think Jennifer Aniston knows, either. As Sloan walks up, Will notes that MacKenzie seems very familiar with TMI. "They have it at my nail place," says the woman we're supposed to believe was embedded in a bunch of nail salon-free war zones for the past two and half years. Lo and behold, it turns out that Sloan goes to the same nail salon, because it's the only nail salon in the largest city in the United States that carries TMI magazine. The women bond over their nails (fuck you, Sorkin) and Will, exasperated over all this talk of trivial women things, tries to leave. He says it's New Year's Eve so he doesn't care if Nina wrote Mein Kampf. He's going to talk to her because he's desperate for a date. Unfortunately for him, it turns out that Nina writes for something much worse than Adolf fucking Hitler's autobiography.
This leaves Sloan and MacKenzie alone. "Really? You're setting up my boyfriend? Well, not my boyfriend, just - whuuuhhaaa!" MacKenzie says, getting cut off at the end by the presence of her actual boyfriend. "Nice," Sloan says, looking disgusted by the whole thing, as she should.
While Kendra parties awesomely in the background (and shows us why one shouldn't go to office New Year's Eve parties, should one ever work in an office that has New Year's Eve parties, which is no office ever), Nina tells Will to kiss her at midnight and then they'll go from there. I guess his inability to maintain any sort of conversation with Nina really turned her on just now. "I've got to start to walk up to people more" says the guy who was dating a cheerleader and a neurosurgeon last week. "You seem lonely and broken to me," Nina says; "but don't worry. I can fix you." That line was amazingly, painfully lame, so Will changes the subject to work. Nina says she's currently writing about Brittany Giancarlo from The Real Housewives of New Jersey. Will has never heard of her, probably because she's not a real person. I don't understand why this show chooses fictional names sometimes and real ones other times. Like, we can namedrop Erin Andrews as Will's St. Lucia vacation-mate but we can't use a real reality show star? We can use real news events but not always real congresspeople? And then there's what comes at the end of this episode, where Sorkin uses a real person and a real tragedy and the deaths of real people to make us give a shit about a bunch of fake people. But more on that later.