MacKenzie says she's not going to keep herself in "jail" anymore. She's going to date a guy and stop feeling bad about cheating on Will three years ago. "He's my boyfriend, we're serious, I want a partner," she says. Emily Mortimer just does not know how to deliver this dialogue. She's especially bad at doing that interrupting-shouting thing Sorkin makes every character do all the time. Please spare her and us and re-cast this role. MacKenzie realizes this conversation isn't going anywhere good and urges Will to make an appearance at the party. Who did Emily Mortimer piss off in make-up, by the way? The foundation on her face is noticeably darker than the rest of her body. She looks nice in that dress, at least.
Will mutters a "fuck" (this is the episode where Sorkin sort of realized that he's on HBO now so his characters can swear) and heads out to the party. Oh! Check out the Rodney Dangerfield guy in his power blue suit! He's the best. Sloan Sabbith, because she is supposedly a lead character on this show even though she's had less screentime and fewer lines than Tess at this point, glides over to Will and compliments him on the tux. He says he just came here from a different, clearly better, New Year's Eve party. But, Will sighs, he's never enjoys New Year's Eve parties. Sloan says she doesn't either, and starts reminiscing about bad New Year's Eve parties past until Will tells her that this is his sad moment, not hers. No walks down memory lane for you, Sabbith! Probably because Sloan doesn't want Will to talk to her anymore, she encourages him to walk up to a woman and start a conversation with her. Will doesn't seem to understand how these things work, even though just LAST WEEK, he was seemingly good enough at flirting to date a bevy of attractive ladies. A Netflix queue of them, one might say! And now he has no clue what he's doing and needs Sloan to point out an available-looking woman wearing a gold dress. Will gets nervous at the prospect of talking to her, admitting to Sloan that he's "not good at this." Except that he is, and we've seen that before. Sloan thinks he's "sweet" and says he should open up to more people. Will tells her to shut up. They have a cute little moment of shared social awkwardness that is kind of ruined when you remember that it's pretty inconsistent with what we saw of Will last week.
Will finally gets the nerve to talk to the woman, who introduces herself as Nina Howard because, yet again, Sorkin can't think of a name that wasn't popular in the '50s. Will shakes her hand and then: "I don't ... know what ... to do." He goes with a "How'd you get in here?" Nina is obviously only still talking to this weirdo because she knows him from TV. She says she's friends with one of ACN's morning show producers. What? Morning show? Blech! They don't do serious news over there, so they should all die! Will clearly looks down on them. He says the day team and the primetime team are like the "Jets and the Sharks." "Maybe we could be like Tony and Maria," Nina says, and we realize that she's still talking to Will because she's just as weird and cheesy as he is.