Sam and Reese go rowing on Central Park, pretending to be on a date, to watch their new Number, Ian Murphy. Finch informs them that Ian is an investor who owns several businesses, and there's nothing suspicious in his background. His uncle died, leaving the orphan Ian $100,000 which he used to start his business. Now Ian is with his current girlfriend, Veronica, rowing on the lake. When Ian says that he has to head back to check on business, Reese goes to his apartment while Sam maintains surveillance on their new Number.
As soon as Ian drops off Veronica, he ducks into a restroom and changes clothing into something hipster. Meanwhile, Reese breaks into Ian's apartment and listens in as Sam describes what Ian has done. She figures that he's a sociopath as he picks up another woman. Finch confirms that Ian is using a date app to link up with women, while Reese finds a hidden compartment in Ian's apartment. Inside are files on dozens of women. Among the files is a flyer on a missing women, Dana Wellington, who died in a car accident a week ago. They wonder if Ian is a stalker or a killer.
Hersh is searching hospitals in New York looking for Root. He calls his superior and informs her that Root probably knows where they can find The Machine, and that he'll check in when he has more information.
Dr. Carmichael brings Root in for another session, and she informs him that she'll be leaving soon. However, she admits that she doesn't know where she is going. Carmichael asks about the Voice, assuming that Root learned the information about him on her own. He figures that Root is suffering from delusions of grandeur and wonders why she's still there if the Voice is all-powerful, and Root admits that she doesn't know. However, she's confident that the Voice has a plan for her.
Root checks on Ian's pervious girlfriends and confirms that Dana is the daughter of a philanthropist and real-estate broker, Bruce Wellington. However, there's no indication that Ian dated her recently, and the only connection he has to Dana is that they attended the same college. As they talk, Finch notices that someone has bought Bear a spiked collar and a large chew-bone. He figures Reese got them, but Reese insists that he didn't. Finch checks Ian's app history and confirms that he makes a lot of pickups at a club, Blur. He offers to get Reese an invitation but Reese says that they should take a different approach and stack the deck.
Carter is pulling over a drunken lawyer when Finch calls and asks her to come to the safehouse that night... and wear something less conservative in even attire. When she arrives there, she finds Sam dressed for a night on the town. Zoe Morgan comes in response to Finch's call and Carter realizes that they're bait. She checks the gun in her purse and Sam and Zoe show off their weapons as well. Finch sets up app profiles for them and Sam is disgusted to discover that Finch has set her up as a yoga instructor. Reese points out that she could relax a bit and Carter says that she'll work on it with Sam in the car.
The three women get to the club earlier than Ian usually does and share a toast to not being called. Fusco is watching them from a balcony above and assures them that he's on watch. Ian finally comes in and, after ignoring an angry-looking Sam, approaches carter instead. She invites him to sit and they talk about how she works as a cop. Ian is seemingly impressed with her and invites Carter over to his place for dinner the next night. Finch tells Carter to say yes and she does. She leaves and Ian apparently follows her, with Fusco following Ian. Carter ducks around a corner and finds Reese waiting for her, and Fusco tells them that Ian has turned off a short distance behind.
The next day at the library, Sam is playing with bear while Finch runs a background check on the money Ian inherited from his uncle. The hacker discovers that the money actually came from Wellington. When Finch checks one of Ian's sim cards, he discovers that he was in the area of Dana's funeral.
That night, Carter goes to Ian's apartment for supper. He points out that she has a nut allergy based on her pushing away a bowl of peanuts at the club the previous night, and but he's impressed with Carter's deductive skills. She admits that she was a homicide detective but that she's comfortable where she is now as a beat cop. Ian walks towards her holding a cutting knife and Carter tenses up, but he then walks past her to the refrigerator to get some shitake mushrooms. Reese and Sam are set up on a roof across the street, and Reese worries that Carter is lowering her guard around Ian. Sam wonders if he has something with Carter and Reese assures her that he doesn't. While they discuss their respective dating lives or lack thereof, Carter gets Ian to talk about how he got started in business. He talks about how he received the $100,000 check from his dead uncle even though he had never met the man.
At the institute, Reese accesses a drug dispensing machine and with the Machine's help faking Carmichael's ID, gets three vials of a sedative.
After they have dinner, Ian walks Carter home and he admits that he enjoyed their date. They kiss just as two muggers approach them. However, one of them addresses Ian by name and they move in on him, knives drawn. Sam fires from the roof, taking out one with her sniper rifle, and Carter shoots the other. Shocked, Ian demands to know what's going on.
Root goes to the air conditioning room in the institute basement and opens the lock after the Machine resets the password for her.
After Fusco takes the two killers into custody, Fusco interrogates them and calls to tell Finch that Wellington's head of security hired them. Carter and the others bring Ian to a safehouse and tell him that they have inside information that someone wants him dead. When Reese asks him about his files, Ian insists that he does it to try and impress women, but admits that sometimes he gets overenthusiastic. Carter wonders why he doesn't have any long-term relationships and Ian tells her that's the point. Finch wonders why Wellington wants him dead and Ian explains that he and Dana met while there were in college. However, Ian came from a poor background and Dana's father always held him against it. When Dana became pregnant, Wellington had one of his people tell Ian that she was having an abortion and pay him to leave time. When Ian tried to call her, Dana ignored him because she was afraid of her father. He stayed away for nine years until she died in the car accident. Ian went to the funeral and when Wellington saw him, he freaked out. Rather than make a scene, Ian left.
The next morning, Sam is playing with Bear at the library and admits to Finch that she got the items for the dog. As Finch and Reese go over Wellington's history, Reese spots a photo of an 8-year-old boy with the philanthropist and realizes that it's Ian's son, Alex. They realizes that Wellington lied when he claimed that Dana got an abortion, and that now the man is worried that Ian came back to reclaim his son. Carter tells Ian what they've discovered and explains that Dana's sister raised Alex. Ian wonders why Dana would lie, and Carter figures that Dana knew Ian wouldn't leave her if he knew he had a son. Carter Promises to set things right and explains that Finch is going to break into Alex's school locker and get a DNA sample from a water bottle. Once they have the results, they can confirm if Alex is Ian's son as they suspect. When Carter says that it should be safe, Ian insists on going with Finch.
Zoe sets up an appointment with Wellington, claiming that Reese is a buyer looking for a privately-owned Picasso. They meet at Wellington's home and while Reese keeps Wellington occupied, Zoe claims that she's going to the bathroom. She lets Sam in instead and they go to the safe. Sam starts to open it so that they can get at the birth certificate papers for Alex inside. As Zoe looks around, she sees boarding passes for Alex on a flight to London.
Finch and Ian go to the school and wait outside until Alex leaves. Finch informs Ina that Wellington has enrolled Alex in a private school in London. However, once they can confirm the boy's paternity, they can use it as leverage to get Alex back. The Machine calls Finch on a nearby payphone and reluctantly leaves Ian on guard while he takes the call. When he deciphers the new Number, Finch realizes that it belongs to Root. He calls the institute and the receptionist tells him that another man has also been asking about Root. Meanwhile, Ian goes over and knocks over the chauffeur picking Alex up, and then takes his place. Alex gets in and Ian says that he's a replacement driver, and then drives off with the boy before Finch can stop him.
Sam gets the safe open but Alex's birth certificate isn't inside. Zoe tells Reese, warning that it will take days to confirm the results of the paternity test. Reese then asks Wellington where Alex's birth certificate is. Realizing that he's been tricked, Wellington tells Reese that Alex will never know that Ian is his father. Disgusted, Reese punches him before the man can call for security. Zoe wonders what they're going to do now.
Ian parks the limo and calls to tell Carte that he's done something stupid. He then sits down with Alex and asks about his "Aunt Dana." Alex admits that he didn't spend a lot of time with Dana, but he misses her, and Ian says that he know how it feels to have someone in your life vanish. He shows Alex a photo of Dana when they were together in college and admits that he wishes he had met Alex a lot sooner. Carter comes over and sends the boy to buy an ice cream cone. Ian admits that he didn't want to lose his son, and Carter promises that they'll get Alex back for him.
When they take Alex to the station, Carter gives Ian Alex's birth certificate and tells him that Ian managed to find it. She asks Ian if he's ready to be a father and he assures her that he is. Ian invites her out for drinks and Carter says that she'd be interested once everything settles down.
At the institution, Carmichael holds an early-evening session with Root and asks why she seems so happy. Root tells him that it's time for her to leave, and that there's a government operative coming to kill her. When Carmichael points out that she needs his signature to leave, Root explains that the Machine will call on Carmichael's phone to tell her when it's time to go. Then she'll lunge across the desk and paralyze Carmichael with a single blow, take his car keys, and drive away. Carmichael wonders how she'll get past the guards and Root explains that she stole drugs from the infirmary and released them into the air conditioning system, after closing the vents to Carmichael's office. They listen and don't hear anyone moving in the institute, and Root says that it's about time for her to go. Carmichael's phone rings, just as Root predicted, and he looks nervously at her as she smiles.
Carter goes out with Sam and Zoe for a drink. They notice that Reese is outside and Zoe tells them that he's there to walk her home. Once she leaves with Reese, Carter goes home to be with her son. Sam turns to Bear, who is sitting on the floor, and tells him that he'll be coming home with her.
At the institute, Root leaves Carmichael's office and hears a phone ring on one of the unconscious staff members. She takes the phone and plugs in the earphones, just as Carmichael staggers out of his office. Root tells him that she probably didn't kill anyone, but warns him that Hersh is on his way and will probably kill Carmichael when he finds him. Hersh arrives and opens fire, and Root returns fire following directions from the Machine over the earphones. She finally shoots behind her where the Machine says, wounding Hersh. Root goes over to finish him off but, much to her surprise, the Machine tells her to spare Hersh as well. She tells Carmichael that she's feeling much better thanks to his help and leaves.
Finch arrives a few minutes later and comes inside. He realizes what Root has done and calls Reese to tell him that they have a problem.