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Lolly Whitehill is an inmate at Litchfield Penitentiary and a former inmate at MDC Chicago with an interest in conspiracy theories. Her heritage is Norwegian and her religion is with the Evangelical Lutheran Church. She's currently in Psych. She is portrayed by Lori Petty.
Lolly appears to experience psychosis in which she has auditory hallucinations and paranoid delusions of persecution. While psychosis is one if the main symptoms of schizophrenia, the audience doesn't see other symptoms of this disorder in her, thus an accurate diagnosis for her is unclear. Lolly believes that various government agencies like the CIA, FBI, FEMA, etc. are after her, and she follows conspiracy theories.
Lolly does not like to take her medications due to the side-effects, so she sometimes struggles with reality and time. Despite her paranoia, she is a nice and considerate person when lucid. Lolly has good rapport with Healy, and discusses her experiences with him. After she admits to murdering the guard found in the garden, she is taken to psych, and begins crying with fear at seeing other inmates restrained.
She is an older (approx young middle-aged) white woman with short, white-blonde hair. In the third and fourth season, she wears glasses.
For a list of episodes featuring Lolly's flashbacks, see here.
Before Litchfield, Lolly worked as a journalist for a free weekly newspaper called Free Weekly, but was turning in assignments about government corruption and surveillance, even though they weren’t assigned to her. In 1993, after she was let go from that job, her friend from work tried to find her a placement in a group home with other mentally-unwell people, but it was an unpleasant place and the triggering effect that the other residents had on her delusions, plus the threat of violence, meant that she ran away. She ultimately ended up homeless and selling cups of coffee out of a shopping cart she wheeled around Seattle, using a stick with bells on to drown out her auditory hallucinations. In 2009, whilst travelling around the streets, a wheel on her trolley broke. Two police officers approached her and told her to move on, thinking she was panhandling. Her voices tried to convince her that the officers meant her harm, which triggered her to start yelling in panic and reach for her bell-stick. The officers assumed she was reaching for a weapon and she was tackled and arrested, most likely for perceived aggravated assaut on a police officer ("It Sounded Nicer In My Head").
Lolly is first seen in "Thirsty Bird" on the plane with Piper while they are flying to Chicago. She seems to be a caring and considerate person, which is shown when she calms the person next to her who has never flown before, and when she offers Piper Vaseline for the long, dry flight to Chicago. It is implied that Lolly has either been in Max or in a really terrible prison, because on the plane she says that she will "probably get fat" from being fed daily. She also says that if the place they arrive at has "heat and a bed; it's better than where I've been".
After being sent to a different cell than Piper when they reach MDC, the next time they meet is in the Prison Yard. Piper is with a group of middle-aged prisoners trying to keep warm when Lolly approaches and greets Piper. Piper barely has time to respond before the leader of the group, Felicia, tells Lolly that her voice annoys her and to keep walking. Lolly says "Fuck you, I'm saying 'hi' to my friend". Felicia asks Piper if Lolly is her friend, and Piper says "We met on the plane..." - but before Piper can finish, Felicia cuts her off and says "I asked you a yes or no question". This leads Lolly to tell her to back off because Piper had (or Lolly thought she had) killed someone with her bare hands. Felicia insults Lolly and tells her to leave, and Lolly responds with "Fuck you, Menopause". Felicia replies "Fuck you, GI Jane Doe" and shoves Lolly. Lolly shoves back, causing the leader to pummel her into the ground. Lolly screams for Piper to help her, but Piper remains where she is until the COs break up the fight. This is the last of Lolly that is seen until Season 3.
As a new inmate at Litchfield, being transferred to Litchfield in "Ching Chong Chang", she raves about the prison being wonderful a number of times. Lolly's praise about how clean it is, and how no one is screaming, continues to prove that she was in a truly awful place at some point. Lolly also seems experienced in prison life; for example, she knew that the Kosher meal is preferable and better than the regular prison food, despite being a Lutheran. Lolly seems to have an obsession with Alex Vause as she is often observed staring at her. Alex also caught Lolly sneaking around in her bunk. When the suspicious behavior from Lolly continues, Alex looks through her bunk and finds a notebook containing notes about Alex's daily routine.
Alex and Lolly are doing maintenance work when Lolly 'accidentally' breaks a Greenhouse window. One person runs off to tell a guard, and Alex goes into the greenhouse to get a rake, but not before looking at the broken glass on the ground. When she comes back with the rake, a big piece of glass is missing, and when questioned, Lolly says she doesn't know what Alex is talking about.
Later, Lolly is in the bathroom when Alex comes in. Alex asks Lolly why she is looking at her, and Lolly says she's not, and to leave her alone. Alex angrily tells Lolly that she's been following Alex all over the prison and tracking her. Alex walks toward Lolly in a somewhat threatening way, calling her crazy and psychotic. Lolly pulls out the large piece of glass because she feels threatened, but Alex is convinced that Lolly has been hired by Kubra Balik to kill her. Lolly tries to stab Alex with the glass, but Alex manages to grab Lolly's wrist and punch her. Alex then starts strangling her, and Lolly chokes out that she will tell Alex everything if she stops. Before Alex can react, Lolly starts telling her that the NSA has been infiltrated, completely surprising Alex. Alex then asks "What the fuck are you talking about?" - and Lolly says, "This whole place is completely bugged. They've been gathering information on me, and they're trying to frame me for treason, and for terrorism". She also tells Alex that she "know[s] you're one of them" and that she will work with her.
After this incident, Lolly is afraid of Alex, so when Alex walks into the bathroom and finds Lolly there, and begins to approach her, Lolly freaks out. Alex still tries to talk to Lolly because she is convinced that Lolly is insane and may try to kill her unless she clears things up, or that she might tell a CO. Going along with Lolly's idea that Alex is working for the government against her, Alex tells Lolly that she's a CIA agent. She also says that she is a double agent, working for Lolly instead of against her, and that the reason Alex choked her was "to throw 'them' off track." She convinces Lolly that if anyone finds out that they are working together, 'they' are going to take her out. Lolly agrees not to tell anyone about the incident.
In "Work That Body For Me", Lolly sees Aydin strangling Alex, and kicks him off her and begins stomping on his neck until he is unconscious. The women attempt to assure Aydin's boss that he successfully carried out the job (via Aydin's secreted cell phone). After Alex returns to kill Aydin, Lolly later helps Alex and Frieda dismember Aydin's body and bury it piece-by-piece in the garden. As the season continues, Lolly's paranoia begins to become a serious threat - especially after a group of prisoners, including Lolly, witness a drone overhead in the yard - and Lolly's delusions, paranoia and unpredictability put Alex (and Freida) in harm's way (after the drone incident, Lolly repeatedly attempts to dig up Aydin's body parts from the garden to either move them or because, as she says to Alex, "they're onto us; they know everything". At this point Freida decides Lolly must be killed (planning to use poisonous Oleander leaves in a tea), to Alex's complete horror. Alex then enlists Red to help protect Lolly and dissuade Freida from her plan to kill Lolly.
We learn that Lolly has psychosis, a mental condition where she sees and hears things that aren't there (hallucinations) and believes things that arent true (delusions). Sam Healy takes her in for counselling and makes her believe that she didn't actually kill Aydin and it was all in her imagination. It is not until after they have found the body the prison is in lockdown in "People Persons" that Lolly - and Healy - realize it actually happened. A distressed Healy turns her in and she is taken to Psych. Healy is visibly very shaken as she is dragged away.
- Piper Chapman - Piper was friendly towards Lolly on the plane on their way to MDC in season two. When Lolly arrived in Litchfield in season three, Piper tried to become Lolly's friend, but she didn't recognize her. Later, Lolly remembers who Piper is and they become friends.
- Alex Vause - Lolly becomes friends with Alex when she begins to work at the garden in season three. She starts to stalk her as she believes she is working for the NSA. Lolly finally believes Alex isn't and the two become friends. At the beginning of season four, Lolly decides to get Alex to go to the lake, and finds Aydin Bayat strangling her, Lolly kicks him off Alex and stamps on his throat until he passes out.
- Frieda Berlin - Alex and Lolly decide to take care of Aydin's body after Alex suffocated Aydin the previous night. Frieda is found inside the greenhouse looking at the tarpaulin which is covering Aydin's body. Alex tries to blame Frieda, but she says that she didn't do it and knows Alex did it. Frieda tells Lolly and Alex that it would be easier to dig six one foot holes rather than one six foot hole. So Frieda, Lolly and Alex take some garden shears and cut Aydin up into six parts and bury him in the garden.
- Sam Healy - Healy drew parallels between Lolly and his own mother who also suffered with delusions. He tried his best to counsel and care for her, and was surprisingly effective. He was very shaken when it emerged that she did kill a CO and checked himself into a psychiatric unit as a result.
- Ann-Marie - Ann-Marie was Lolly's best friend and co-worker at Free Weekly. When Lolly was fired as her delusions become more apparent, Ann-Marie decided it was best for Lolly to be taken to a care home as Lolly's family did not live nearby and Ann-Marie herself was pregnant and so could not care for Lolly.
- NSA etc. (perceived)
- Felicia - Felicia attacked Lolly in MDC after Lolly insulted her, claiming Piper to be her friend.
- Aydin Bayat - When everyone escapes to the lake at the beginning of season four, Lolly decides to find Alex and ask if she wants to come along, when Lolly walks in, Aydin is strangling Alex under order of Kubra. Lolly kicks Aydin off Alex and stamps on his neck repetitively until he passes out, but Lolly thinks she killed him, as does Alex.
- Lolly had been arrested for public vagrancy, disturbing the peace, nudity, solicitation, and disorderly conduct, as mentioned by herself in "It Sounded Nicer in My Head".
- "That's some shit, man."
- — Lolly Whitehill ("Thirsty Bird")
- "And may I say, I think y’all are doing a wonderful job controlling the media.
I mean ‘we’ — we are doing a wonderful job!"
- — Lolly Whitehill, trying to convince Rabbi Elijah of her Jewish faith ("Where My Dreidel At")
- "Oh, I like the kitty with the heart eyes. And the alien. But that's not how aliens really look."
- — Lolly Whitehill to Alex ("Power Suit")
- "It's okay, we just keep trying."
- — Lolly Whitehill to Mr. Healy ("It Sounded Nicer in My Head")