Will and Jim try dating this week, as even though Will was supposedly very good at dating just last episode, he is now bad at it and requires assistance from Dr. Dr. Sloan Sabbith (she has two Ph.D.s now!) to set him up with a woman at the ACN New Year’s Eve party. Because who doesn’t want to go to work on New Year’s Eve? Jim loves it, because he gets to do actual work there until Don decides to set him up with Maggie’s roommate, Lisa. Dr. Dr. Sloan fixes Will up with a woman who is a writer for a gossip magazine called TMI, and Will can’t help but get on his News High Horse and tell her that she’s worse than a heroin dealer because people like to read about The Real Housewives of New Jersey. Needless to say, she does not appreciate this, and a few days later, a slightly fictitious account of the night and Will’s behavior appears in Page Six.
Dr. Dr. Sloan then sets Will up with a woman who loves guns and drugs, thus earning her a very special Willecture. And Date #3 talks about how much she loves The Real Housewives of New Jersey, so she also gets a Willecture. Willectures for all women! And then it all makes it into the gossip columns, with Date #2 getting the front page of TMI and Will looking like a gun-loving drug addict. That’s when Charlie realizes that this is the work of Jane Fonda, who is using her other AWM outlets to take Will down so she’ll look justified in firing him, just like she promised last episode. Charlie didn’t tell Will about that meeting. Now they have to figure out what to do about it. Also, MacKenzie is very sad to find out that Will’s non-compete clause is only in his contract because he had to put it there to have the ability to fire MacKenzie.
Jim’s date with Lisa goes much better than any of Will’s. Though he tells Maggie that they didn’t really hit it off, he sleeps with Lisa and Maggie finds out, thanks to Don, who isn’t stupid and therefore can see (as can Lisa, although I guess she didn’t really care) that Maggie has feelings for Jim. The whole gang end up at work on a Saturday – Charlie, MacKenzie, Don, and Will to deal with the TMI story and everyone else to listen to Neal’s lecture on the existence of Bigfoot, which he’s been weirdly obsessed with all episode. Maggie takes this opportunity to yell at Jim for sleeping with her roommate and lying to her about it in front of everyone, so he makes her sit at the assignment desk for the rest of the day as punishment.