When Jake notices ants on his desk, he wonders whether they got rid of all the food crumbs around the precinct - and looks directly at Hitchcock and Scully to see. Amy is horrified to see the ants are using the monitor cable between her and Jake's desks to cross to her side. Gina tries to fight the ants with Charles's cologne which is repulsive to everything. The Captain suggests the ants are trying to escape the cold, so they open all the windows to make the precinct colder. The freezing cops celebrate, until the ants get into their winter coats.

At a courthouse, Jake doesn't want Sophia to know he's waiting for. Jake admits to Terry that things have been weird between them lately with Sophia seeming distant. When Sophia runs into Jake, she says she can't hang out tonight as she has a public defenders charity ball tonight. Sophia offers to take a walk around the park with Jake right now.

Elsewhere, Rosa escorts Deputy Chief Wuntch to Captain Holt's office. Wuntch explains she's a front-runner for a job in the Boston PD and needs Holt's recommendation to get the job. Holt is delighted to hold Wuntch's fate in his hands. Meanwhile, Gina deliberately spills a milkshake on Boyle's crotch. Gina is angry that Boyle is no longer trying to split their parents up. Lynn Boyle wants to marry Darlene Linetti and asked for Gina's permission, which she's refused to give. Amy is excited to mediate the dispute between her co-workers.

When they sit down on a bench in the park, Sophia tells Jake that she hasn't been assigned any of the top cases by her boss because she's dating a cop. Sophia says her job is really important to her, and asks Jake if they can press pause on their relationship. Since it's for her career, Jake agrees.

Back at the precinct, Jake talks to Terry in the break room, explaining how he plans to fix Sophia's work problem. Jake plans to befriend her boss, Geoffrey Hoytsman, after gathering his interests from Facebook. Jake invites Terry to join him at the charity dinner tonight, where he'll try win Hoytsman over. Meanwhile, Holt asks Rosa to his office to talk about his dilemma with Wuntch. When Rosa tells Holt to take the high road, Holt tells "Mother Diaz" she can leave now.

At the party, Jake and Terry feel uncomfortable surrounded by defense attorneys. Sophia is nervous when Jake explains he's going to try bond with her boss. When Hoytsman comes over to talk to them, Jake's attempts to chat about skiing and Atlantic City fall flat. When Jake wonders why Hoytsman would visit Atlantic City so often if he hates the place, he figures he might like something there - gambling.

When Amy and Boyle confront Gina in the break room, Charles explains he's and Amy have drawn up a list of things he'll promise not to do around Gina if she'll give his father her blessing. Gina admits her trepidation isn't about her and Boyle's lives being intertwined, but that she doesn't want to see her mother hurt again. When Boyle asks Gina to talk to do his dad to see how he would never hurt Darlene, Gina agrees.

As Hoytsman prepares to leave his conversation with Jake, Jake bets him that he can't name three of the hors d'oeuvres. Hoytsman takes Jake's bet and wins. Their series of bets continue with challenges to throw food into people's drinks, guess Terry's height in egg rolls, and take a glass of champagne without knocking the tower over. When Hoytsman excuses himself to go the bathroom, Jake follows soon after and finds Hoytsman snorting cocaine.

Back in the ballroom, Sophia is anxious that Jake will wreck things. Terry reassures her that although Jake is stupid, he's also smart, and says he thinks Jake's plan is working. Then, Jake drags Hoytsman out of the bathroom in cuffs. Hoytsman attracts the attention of the party goers by shouting that Jake is arresting him. Elsewhere, Captain Holt tells Rosa the deed is done. After listening to her advice, he decided to give Madeline Wuntch a good recommendation.

In the interrogation room, Gina questions Lynn Boyle, as Charles and Amy watch on from the other side. When Lynn says that Darlene is the best thing that ever happened to him, including Boyle, Gina gives him her blessing to marry her mother. Back at his desk, Jake questions Hoytsman as Sophia arrives. Sophia says she's there as Geoffrey's lawyer, not to see Jake. When they argue, Sophia accuses Jake of being such a cop, while Jake says she's such a lawyer.

Sophia tells Jake they're done, not with the case - with the relationship. As Sophia leaves, Jake rushes outside to talk to her. Jake thinks they shouldn't break up over this, but Sophia says their jobs and lives are incompatible. Although Jake's willing to put the work into the relationship because it's serious to him, Sophia it's not so serious to her and she isn't willing to put the work in. Elsewhere, Captain Holt goes to Madeline Wuntch's office to give her tickets to see Wicked in Boston. Wuntch thanks Holt for the recommendation, but says she won't be going to Boston. She was only using that job as leverage to get a promotion at the NYPD. Now, she has more power over Holt than ever before. Before he leaves, Wuntch kisses Holt and gives him back his theater tickets.

At a bar, Boyle toasts Amy for fixing things between him, Gina and their parents. Gina is excited to plan the wedding. Meanwhile, Jake and Holt drown their sorrows at the bar. When Jake says he shouldn't have gone to the party or arrested Sophia's boss, Sergeant Jeffords says Jake did everything right as a cop and he put himself on the line for his relationship. Terry says Jake should be proud. Despite Terry's kind words, Jake and Holt don't feel any better, so they decide to get soused.