A young Mindy watches When Harry Met Sally, a high school Mindy watches You've Got Mail, a college Mindy watches Notting Hill as a rowdy frat party is in full-swing in her building. Her voice over explains, "You have an idea of how your life is going to work outâ€¦"
MINDY, stands in a room with fellow resident doctors and examines a pregnant patient. Slick British doctor JEREMY REED hits on the pregnant lady then winks at Mindy. The patient is assigned to no-nonsense DANNY CASTELLANO, much to Mindy's dismay. Just then, Mindy notices a cute doctor walk by. A meet-cute elevator scene (complete with files falling and the elevator stopping), Mindy explains, leads to, TOM, the cute doctor and her, moving in two months later.
A correctional officer stops her voice over and in current day asks Mindy what her story has to do with her present arrest.
Tom got married last night, Mindy explains. Not to her, but the Serbian girl who sells bagels in the lobby of the hospital. They invite Mindy to their wedding; she attends and consumes a lot of alcohol. An embarrassingly awkward speech later, she grabs a bottle of champagne and books it out of the wedding. Mindy drunkenly wobbles on a bicycle which she rides right into somebody's pool. Underwater, a forgotten Barbie doll chastises Mindy and she realizes "this is not where I want to be." Hence, her arrest for disorderly conduct.
At the police station, Mindy is bailed out by her sweet best friend, GWEN who takes her back to Mindy's office. As Gwen's daughter plays near-by, Gwen tells Mindy she's "high-risk" and is going to call off the blind date she has set up for her. Mindy convinces her not to. Gwen also warns Mindy to stop hooking up with Jeremy because "he's Hugh Grant in real life." Mindy's assistant arrives to tell her that her patient is in labour â€" the one with the insurance. Mindy runs through NYC traffic (still in last night's trashed wedding dress) only to find out that Danny has already delivered the baby and stole her patient. Mindy storms after him into the doctor's lounge where Jeremy hangs out. Jeremy defends Mindy and Danny leaves stating that he's smarter than both of them. Jeremy compliments Mindy's "trashy" look and suggests they "hang out deep" but she reluctantly declines and runs out of the lounge â€" but not before taking a discreet photo of him and sending it to Gwen: "I did not do this."
The next day Mindy arrives at her office to find Nasrin, a Muslim lady, and her son needing her services. But they're uninsured. She tries to tell them she can't take Nasrin on as a patient but caves and says yes if they just say they promise to have insurance. Later, Mindy runs up to her assistants and asks them why they sent her a patient with no insurance. "I thought she might be rich with oil money," her assistant Shauna tells her. "Well, she wasn't. She was poor with nothing money," Mindy exclaims. And Mindy is not good at saying no.
Mindy models her date outfit for her assistants, Shauna and Betsy: a bright blue mini skirt and glittery silver top. Danny, filling out files nearby, tells Mindy that is not a date outfit. Doctor SHULMAN, the owner of the clinic enters and compliments Mindy's outfit, reminding her kindly that "she's worth waiting for." As he leaves Danny claims that Dr. Shulman probably hates the outfit and that she should be simple and comfortable. Mindy scoffs that she'll just take advice from a guy who gets all the ladies â€"just ask his wife, "I mean his ex-wife." Upset, Danny leans in and tells her, "you know what would really look great? If you lost 15 pounds." He walks away as Jeremy appears and tells her not to listen to him because she's beautiful. Several moments later, Mindy and Jeremy sloppily make out all over Jeremy's desk in his office. She quickly shuts it down and runs out of the office.
At the end of the day, Mindy gets on the elevator in a pretty red dress and smiles. Danny steps in the elevator and tells her she looks nice. "Go to hell!" she spits as the doors close.
Before her blind date, Mindy prays in the cab outside of the restaurant: "Dear Lord, please let this date be good. May he have the wealth of Mayor Bloomberg, the personality of Jon Stewart, the face of Michael Fassbenderâ€¦" she pauses. "The penis of Michael Fassbenderâ€""the Cabbie starts his meter again and Mindy hops out of the car. Her date DENNIS compliments her appearance and the date goes well as Mindy subtly runs down her list of "Red Flags." Interrupted by a phone call from Nasrin's son, saying she's in labour, Mindy first brushes him off then caves and cuts the date short to go deliver a baby.
Mindy races to the clinic, changes and delivers Nasrin's baby as Danny watches in awe. Later, in the doctor's lounge, Mindy happily watches When Harry Met Sally. Danny walks in and makes fun of the movie, irritating Mindy. He asks about her date and Mindy starts telling him how perfect he is. "Yeah, but was he a man?" he asks. "Is he the kind of guy who if you heard glass breaking in the middle of the night, is he going to jump out of bed, say 'stay here' and look through the house naked with a baseball bat or is he gonna hide under the covers with you? Is he the kind of guy who is going to get grossed out when you give birth or is he going to dry your forehead and tell you that you look beautiful while all that disgusting stuff if coming out of you? Is this the kind of guy who is not afraid to get into a fist fight at a Springsteen show because someone really disrespects himâ€""Mindy tells him he's just describing himself.
He sits beside her and compliments her patient's delivery. She accuses him of trying to steal her patient â€" again â€" and he tells her he has to stay on his toes and know when to pounce "you know, with this economy and all." She chuckles and congratulates his tiny joke. Mindy tells him that this morning she woke up broken up about Tom and her life, but today she delivered a baby into the world and is watching one of her favourite movies. "This is progress!" Danny grabs the remote and abruptly changes the channel. "I am sharing my feelings with you!" she yells. "I wanna share this show with you," he tells her. She glares at the television show â€" fishermen wrestle a shark on a boat.
Mindy lounges on her sofa and speaks to Gwen on the phone. She tells her that maybe Dennis was too perfect and possibly a serial killer. Her doorbell rings and Gwen asks her who it is. Mindy tells her it's delivery for 'clear soup.' She opens the door to reveal Jeremy, who grins and walks to her bedroom. Mindy tells Gwen that she really is changing â€" if not tomorrow, then the next day. She hangs up and smiles at Jeremy.