The characters of Every Breath You Take. Be aware of potential spoilers.
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Wakeling family
Virginia Wakeling
Virginia "Ginny" Wakeling
The widow of self-made real estate magnate Robert "Bob" Wakeling, a philanthropist and trustee of the Metropolitan Museum of Art. Three years ago, she fell to her death from the roof of the Met during a gala, with foul play being strongly suspected but never proven.
- Affectionate Nickname: Her boyfriend Ivan affectionately called her Ginny and still refers to her this way three years after her death. He says that she used to go by this nickname before she married Bob, who insisted on her going by her full name as it was more dignified.
- Anti-Nepotism: She shut down her nephew Tom's attempts to get a position at Wakeling Development simply because they were family, feeling he wasn't capable or responsible enough to work there. She had also planned to change her will to leave the majority of her money to charity rather than her children and nephew, to prevent them from becoming lazy and entitled; Virginia was especially concerned about her son, who only put in the bare minimum of effort at Wakeling Development and was clearly content to coast by on his inheritance for the rest of his life.
- Dies Wide Open: When her body was found, it's noted her eyes were still wide open, her face frozen in fear. Considering she was likely thrown off the roof of the Met by someone she knew, it's not surprising her last moments were filled with shock and terror.
- Disney Villain Death: Inverted; she wasn’t a bad person yet met her end by falling from the roof of the Metropolitan Museum of Art. The investigation concluded she was almost certainly thrown off by another person, as she didn’t appear to be suicidal and the roof’s architecture would make an accidental fall highly unlikely.
- Has a Type: While they differed in many ways, one notable thing Virginia's two great loves, Bob and Ivan, had in common was that they were both hard-workers who valued being self-sufficient and putting in effort to earn things, something Virginia admired.
- The Lost Lenore: For Ivan, her would-be fiance. Laurie initially thinks he cares more about clearing his name and that he possibly killed Virginia himself, but he insists he genuinely loved Virginia and is still torn up by her death three years later, even if he doesn't always show this openly. Laurie comes to realise his grief is genuine. He often reminisces about Virginia and the life they could've had together, with the situation being worsened by the fact he's suspected of killing her, wrongly as it turns out.
- Obnoxious In-Laws: There was little love lost between her and her brother-in-law Ken; Virginia took her husband's side in his dispute with Ken over Wakeling Development, believing that Ken wasn't entitled to any of the company assets because he hadn't worked for it and that he was out-of-order for demanding 'his' share. She also believed that Ken had passed down his sense of entitlement to his son Tom; she had a low opinion of Tom's money-grubbing and lack of responsibility. Tom recalls that the last thing she said to him was that he was "even more useless than [his] father" (who at least had gained some success as an architect).
- Parent with New Paramour: Neither of her kids, or her son-in-law for that matter, were impressed by her dating Ivan Gray a few years after she was widowed. They were openly wary and disapproving of Ivan because he was much younger than Virginia and she was extremely generous towards him; they believed Ivan to be a manipulative gold-digger who was making Virginia look foolish. Virginia believed that her children were just being overprotective and having difficulty accepting she was moving on from their father and focusing on rediscovering herself (she had made a lot of personal sacrifices to support both them and their father as they were growing up). Ivan felt that the kids couldn't accept that Virginia's life didn't just revolve around being "Mrs Robert Wakeling" anymore, blaming him for that despite his efforts to get along with them. After Virginia's death, Anna, Carter and Peter were quick to point the finger at Ivan.
- Posthumous Character: The prologue is mostly told from Virginia's perspective during her final hours alive at the Met Gala; by the main events of the story, she's been dead for three years and the plot revolves around solving her murder.
- Wealthy Philanthropist: She dedicated a lot of her time and the immense wealth she inherited from her late husband to various charitable causes, particularly the arts. Virginia privately mentioned that whatever Bob's flaws as a spouse, she was always grateful that his money enabled her to support causes she was passionate about. Ivan says that Virginia willingly lent him thousands of dollars to start his own gym. It's also rumoured she was going to alter her will to leave all her millions to charities.
- You Remind Me of X: Jerry remarks that Virginia reminds him of his own mother, whom he watched blossom and get a new lease on life once all her children had grown up and left home: "It's like she spent her whole life as a moth and then became a butterfly." Virginia was similarly starting a new life that revolved more around herself than just being a mother and moving out from under her late husband's thumb, only for that life to be violently cut short. Jerry finds it especially tragic that she only briefly got to enjoy being independent and re-discovering herself.
Carter Wakeling
Carter Wakeling
The eldest child of Virginia and Bob Wakeling, older brother to Anna and brother-in-law of Peter Browning. Although he's the elder sibling and also works for the family real estate business, he answers to his sister much of the time and is more interested in using his wealth to fund a lavish playboy lifestyle.- Childish Older Sibling: He's only two years older than his sister (he's 41, she's 39), but he's always been far less responsible than her and has the maturity of someone half his age. While Anna can be a bit of a snob, she at least works hard as head of Wakeling Development, while Carter barely puts any effort in at work and is even more outwardly entitled and petulant.
- Entitled Bastard: He strung Penny along for some time, constantly putting off making their relationship public, then ditched her after his mother died and didn't speak to her for three years. He then calls her out of the blue to tell her not to speak with Under Suspicion because it could look bad for him and his family. Penny says she'll think about it, then gets in contact with the show herself, telling herself and later telling Carter to his face that she doesn't owe him anything after the way he treated her. Carter later concedes she has a point.
- Foolish Sibling, Responsible Sibling: The Foolish Sibling to Anna's Responsible. Carter never had much interest in the company, only puts in the bare minimum of effort at work and comes off as a spoilt, immature skirt-chaser whose only long-term relationship fizzled out within a few years. He was once unfavorably compared to his layabout cousin (though Tom has since cleaned up his act) and he's got difficulty controlling his temper.
- Hair-Trigger Temper: He is easily provoked to anger, especially if he believes things aren't going the way he wants. He got into a public argument with his brother-in-law at the Met gala about his mother's will until his sister calmed him down by reminding him where they were and he quickly goes on the defensive during his interview with Laurie and Ryan; he gets mad enough to try and physically stop the camera rolling and punches Ryan when he intervenes. Laurie and her team wonder if he could've been riled enough to kill his own mother during a argument.
- Jerkass Realization: His brawl with Ryan appears to have literally slapped some sense into him, as he realises just what a selfish and ungrateful tool he's been for much of his adult life, to the point he's seriously considered a suspect in his own mother's murder. He quickly arranges to meet his ex-girlfriend Penny and apologises for the way he treated her, telling her he wants a second chance to be with her and that he intends to work harder at the family company to prove he's not just a layabout who lives off his family's fortune.
- Manchild: Although he's forty-one years old, he barely makes an effort at work, with it being implied the only reason he has a such a high position at Wakeling Development (or any position at all, for that matter) is because he owns half of the company's shares and his sister lets him stay. He prefers to live off his substantial inheritance, indulges in numerous luxuries and has never done any real work in his life. Ivan got the impression he was a spoiled child who never really matured, with his own mother telling him he had to grow up sometime. When things don't go his way, Carter becomes petulantly angry and demanding, reminding Laurie of the tantrums her son used to throw as a toddler. The way he treated Penny - insisting on keeping their relationship secret, then casting her off - also comes off as childish for a man who was in his late thirties.
- Spoiled Brat: Ivan openly calls him "spoiled" and he's not wrong; since childhood Carter was raised in extreme wealth and privilege, with his father grooming him to take over his company and openly favoring him over his sister. Carter had no interest in the company but was happy to use his family's riches on a luxurious lifestyle, never having to face any real hardship or consequences. His attitude didn't improve as he aged; by his late thirties his own mother came to feel he was lazy and entitled, telling him he needed to buck up his ideas and actually earn his keep. When he learned his mother was considering cutting him off from inheriting her money, thus forcing him to get a job, he practically threw a tantrum and tried to recruit his sister and brother-in-law to stop Virginia "no matter what". Despite having agreed to be interviewed for Under Suspicion, he also turns up half an hour late, demands they reschedule and snarkily says it's "[their] problem" when Laurie says they don't have time, then tries to snatch the camera and throws hands with the host.
- Starter Marriage: He was briefly married in his early 30s, but got divorced after only a few years and has since sworn off marriage, preferring casual relationships. It's mentioned that his mother was disappointed, as she hoped he'd find love and settle down like his sister. Penny had hoped he would marry her, but this ultimately didn't happen. Near the end though, he tells Penny he wants to give their relationship another shot and take things more seriously this time.
Anna Wakeling
Anna Wakeling
The youngest child of Virginia and Bob Wakeling, younger sister of Carter and wife of Peter Browning. Despite being the younger sibling, she is the current head of the family real estate business and matriarch of the family in general.- Breaking the Cycle of Bad Parenting: While she loves and respects her late father, she acknowledges he could be old-fashioned and sexist; he fully expected her older brother to be the one to take charge of Wakeling Development simply because he was his son and she had to push to show him she was just as interested and capable (more so, in fact) despite being a girl. Anna now has a son and daughter of her own and she's actively raising them to not have the same restrictions and expectations placed on them because of their sex that she and her brother did.
- Foolish Sibling, Responsible Sibling: She's the Responsible Sibling to Carter's Foolish. From an early age she was eager to be involved in her father's company and showed a good head for business. She puts in a lot of work to keep Wakeling Development profitable and generally has a cool, collected demeanour. She also has a happy marriage and two children.
- High-Powered Career Woman: She's the head of real estate company Wakeling Development and is a shrewd, no-nonsense businesswoman who proves a tough shell to crack. Although she was technically born into the family business, her father always expected her older brother to be the one to take over the company simply for being the firstborn and a man, with Anna having to fight to prove her capability to both her father and others in her male-dominated environment. Unlike some other examples, Anna doesn't have too much difficulty balancing work with a relationship and motherhood; it's helped by the fact her husband works with her as a corporate lawyer and doesn't have a problem taking orders from her, plus she can afford a nanny to help with the kids.
- I Reject Your Reality: She absolutely refuses to consider the possibility that Ivan not only didn't kill her mother, but that he sincerely loved her and they were serious about getting married, even when presented with evidence to contrary. In particular, Ivan and Virginia had discussed Anna's husband drawing up a pre-nup for them to protect the family's assets and had gone ring shopping together; it's also pointed out to her that she can't prove Ivan stole the money he used to start up his gym and therefore he had no motive to kill Virginia (even if Ivan was a Gold Digger, it would make no sense for him to kill Virginia). Anna just dismisses this while providing no evidence to back-up her beliefs. Even when she realises Carter could've been involved, the next day she's convinced herself this is nonsense (though this is indicated to be because she's horrified at the thought of her own brother killing their mother).
- The Maiden Name Debate: Defied; her husband's surname is Browning, but something Laurie takes note of is that Anna introduces herself as Anna Wakeling. Anna fought hard to be involved in running her father's company and legacy (which is explicitly named Wakeling Development to reflect this), so she didn't want to change her surname because of how important the Wakeling name is to her. It's implied another factor in her keeping her name is that Anna chafed under her father's outdated views on gender roles and is actively trying to be a more progressive parent to her own kids.
- Past Experience Nightmare: She's had recurring nightmares the past three years about her mother's final moments, including waking suddenly from another of these nightmares following her interview with Ryan.
Peter Browning
Peter Browning
The husband of Anna Wakeling and son-in-law of the late Virginia. He also serves as the family's lawyer.- Henpecked Husband: It's clear that his wife Anna is the more domineering of the two; she's the one who calls the shots when it comes to the family's business and reputation and while she relies on Peter for legal advice, he tends to defer to her. They both appear to be happy with this arrangement, although it does pose some challenges for the Under Suspicion team, as Anna insists they be interviewed together and Peter is unlikely to reveal anything without Anna's say-so.
- Like a Son to Me: He was close to his mother-in-law Virginia, to the point Ivan says that Peter was like "a third child to her"; she also trusted him enough to make him her personal lawyer.
- Mistaken for Cheating: The Under Suspicion team consider the possibility that he was Penny Rawling's lover, which could explain why Penny and her boyfriend were so secretive. However, when asked about it in-directly, Penny says the idea of her and Peter having an affair is ridiculous, while Peter never indicates he thought of Penny as anything but a work acquaintance and that he and his wife have been Happily Married. It turns out that Penny was actually seeing Carter.
Tom Wakeling
Thomas "Tom" Wakeling
The nephew of Bob and Virginia Wakeling; his late father Kenneth Wakeling was Bob's younger brother. Initially considered the black sheep of the Wakeling family, he now works for the family company and is eager to remain close to the inner circle.
- Black Sheep: He was considered this to the Wakeling family; his father had a falling out with his uncle over the family's real estate company, with their estrangement passing down to their offspring. Tom resented his cousins for being born into wealth and privilege, which he was eager to share in. However, Tom wasn't willing to work for it, bouncing from one job to the next and wasting money on partying, while trying to use his family name to get favours. This didn't much endear him to his aunt and cousins, with his aunt especially refusing to let him anywhere near the family's assets. After Virginia died, Tom managed to clean up his act and mend bridges with his cousins, resulting in him being hired to work for the company and doing well for himself.
- Evil Nephew: It's revealed he was the one who murdered his aunt Virginia; after he tried to talk her into letting him join Wakeling Development and/or have more access to the family fortune, only for Virginia to coldly rebuff him due to his lack of responsibility, he tossed her off the roof of the Met in a rage. Tom then took advantage of his cousins' grief for their mother to wheedle his way into the fold, while letting Virginia's innocent boyfriend be blamed for her death. Tom appears to feel some regret and guilt for killing Virginia, but he ultimately cares more about what it gained him; he even tries to claim it was accident and that it wouldn't have happened if Virginia had just given him a chance, despite her having good reasons not to trust him.
- The Gambling Addict: The reason his aunt was reluctant to trust him with both money and the family company is because he used to be heavily involved in gambling, blowing a lot of money on it over the years and getting into at least $50,000 worth of debt. Following his aunt's death and his hiring at the family company, he quit gambling and managed to pay off his debts with the money he conveniently inherited from his late aunt.
- Nepotism: The main reason he was hired at Wakeling Development is because he's related to the company's founders and primary shareholders. That said, Tom has managed to prove himself a capable worker, with his cousin Anna publicly vouching for him.
- Never My Fault:
- He blamed his aunt and cousins - especially the former - for his financial struggles and lack of stability in his younger years, thinking of them as spoilt, hypocritical snobs who lived off his Uncle Bob's fortune while refusing to give him chance to be part of the family empire. He doesn't like to be reminded he could never hold down a job and frittered away money on gambling and parties, getting into a lot of debt, which is pretty good reason for his family to not trust him with their business and money.
- He insists to Laurie that he didn't deliberately throw his aunt off the roof, instead saying he tried to grab her to stop her leaving, she pushed him away, stumbled and accidentally fell. As Laurie notes, there's no way for this version to be physically possible, as the ledge around the roof - also topped by a hedge - is too high for someone to accidentally trip over (especially Virginia, who was only 5'4"). Laurie thinks that Tom sounds so sincere and desperate when telling her this, he might even have genuinely convinced himself this is how it happened over the years to relieve his own guilt.
- Rage Breaking Point: He got into an increasingly heated argument with his aunt about her refusal to let him be involved in the family company and her criticism of his job-hopping and gambling. He started off trying to reason with her, but the moment that sent Tom completely off the rails was when Virginia told him "You're even more useless than your father" and tried to walk away, prompting him to kill her. Even he appears shocked he was capable of it, to the point he's tried to convince himself he didn't mean to do it.
- Secretly Selfish: Tiffany believed he gave her a false alibi - telling the cops they were together the whole night of the Met gala - to protect her after she tearfully confessed to him her impulsive theft of a bracelet from an exhibit. However, she and Laurie come to realise Tom only did this to give himself an alibi as well, for his aunt's murder.
- Shock Value Relationship: It's obvious he brought the eccentric, working-class Tiffany as his date to the Met Gala purely to show up his family, whom he saw as snobs, and get attention for himself. They stopped dating not long after that and Tiffany makes it clear she was aware how out-of-place she was at the gala and that there wasn't much of a real connection between her and Tom.
- Strong Family Resemblance: Downplayed; Laurie notes that at first glance he doesn't much resemble his cousins, but that up close she notices he has high cheekbones like Anna and a long nose like Carter; presumably they inherited these shared features from their respective fathers, who were brothers.
Bob Wakeling
Robert "Bob" Wakeling
The founder of multi-million dollar real estate company Wakeling Development. He was the husband of Virginia, the father of Anna and Carter and paternal uncle of Tom. He died five years before Virginia's own untimely death.- Control Freak: It's indicated he could be quite controlling, especially towards his wife, with Virginia herself remarking he was "domineering". Ivan says that Bob didn't like Virginia using her old nickname "Ginny" because he felt it wasn't dignified enough and Virginia noted that although Ivan is just as hardworking as Bob, he's a lot more laidback. Although Virginia loved Bob and mourned his death, it's noted by several people that she was enjoying her newfound freedom after she was widowed, with the implication that most of her married life revolved around doing what Bob wanted first and foremost.
- Cool Uncle: Although he was on bad terms with his brother, he had a soft spot for his brother's son Tom; Bob blamed Ken for Tom's "lack of focus" in his youth and had decided to bequeath him $125,000 in he and Virginia's joint will. Virginia felt differently, altering the will so that Tom would only receive $50,000 after Bob's death; she may have planned to alter it even further so that Tom received even less money.
- Hair-Trigger Temper: His family - especially his wife Virginia - mentioned he could be hot-tempered and that it didn't take much to set him off. His son Carter has inherited his anger issues, though not his work ethic.
- Parents as People: His children - especially Anna - think of him fondly, but they admit he has his flaws, in particular having outdated and restrictive views on gender roles. Anna had to push hard to make her father see she was passionate and capable when it came to the family business, with Bob having assumed his son would be the one to take over simply because he was a boy and the firstborn (though when Bob realised this, he didn't try to block Anna from getting involved and Virginia believed he would've been proud to see her take charge). Conversely, Carter had little interest in Wakeling Development and disliked his father dragging him along to meetings or constantly discussing real estate with him, resenting that Bob expected him to be enthusiastic about it just for being his son.
- Posthumous Character: He died of a heart attack five years before Virginia's death and eight years before the present-day events of the story. He's mentioned several times by his surviving family and his feud with his brother turns out to be relevant to Virginia's murder.
- Self-Made Man: He started out as a man of modest means but with a good head for business and real estate. He managed to build Wakeling Development from the ground up, to the point he was a multi-millionaire within a decade or so.
Ken Wakeling
Kenneth "Ken" Wakeling
The younger brother of Bob Wakeling, father of Tom Wakeling, brother-in-law to Virginia and paternal uncle of Carter and Anna. He was an architect who initially co-founded Wakeling Development with Bob, but he left the company early on due to their initial lack of success. After the company became profitable, Ken and his brother had a bitter falling-out that was never resolved until the day they both died.
- Posthumous Character: He died about a decade before the main events of the story, round about the same time as his brother. His son, niece and nephew note that both Ken and Bob went to their graves with their feud unresolved.
- The Resenter: He came to resent his brother Bob for his great success with Wakeling Development. Ken felt that he was entitled to share in the company's profits or be allowed back in because he'd helped found the business, only for Bob to point out that Ken had bailed out after just five years and that it was under him alone that the company found success. This caused a lot of bitterness between the brothers that they never resolved; Tom recalls his father even had them move apartments when he was in high school because Ken couldn't stand looking out on the properties Bob had developed.
Others
Ivan Gray
Ivan Gray
Virginia Wakeling's personal trainer and boyfriend of two years, who has since opened a successful private gym, PUNCH, using money he claims Virginia gifted him. He is considered by many people, especially Virginia's family, to be the number one suspect in her death, prompting him to approach Under Suspicion about investigating the case to clear his name.- Clear My Name: He is encouraged by Ryan Nichols - who is taking boxing lessons from him - to pitch his case to Laurie in order to finally clear himself of killing his girlfriend Virginia Wakeling; Ivan insists that despite what the Wakeling family claim, he was genuinely in love with Virginia and would never have stolen from or harmed her. He's cleared of suspicion after Tom Wakeling is revealed as the true killer.
- Et Tu, Brute?: While he was well-aware that most of Virginia's family were ready to believe the worst of him, he was shocked and hurt that even Penny turned on him, going along with the family's claims that he was just after Virginia's money. Ivan says he and Penny usually got along well, not to mention she saw him and Virginia together more often than the family, so she would've seen that their love was genuine. He can't understand why she would throw him under the bus like that unless she had some ulterior motive. The Under Suspicion crew figure it was to try and stay in the Wakelings' good books, in particular her secret boyfriend, Carter, who was convinced Ivan killed his mother. Given that Carter dumped her not long after, Penny was also feeling pretty bitter about romance in general, telling Laurie and Ryan that while she did think Ivan was in love with Virginia, she doesn't think he would've been interested at first if she didn't have money.
- Not with Them for the Money: Many people, including Virginia's family, assume that Ivan was only with Virginia because she was a multi-millionaire who was extremely generous towards him, especially as he was over twenty years her junior. While Ivan says he appreciated Virginia gifting him $500,000 to help start his own gym (which her family insists he actually stole), he wanted to be with Virginia because he was in love with her and they made each other happy, insisting that their large age-gap never concerned him. Penny states she thinks that Ivan probably wouldn't have been interested in a woman two decades older if she hadn't had money, but that it doesn't mean that they weren't genuinely in love, noting that lots of people have certain standards about their partners having financial security and she thinks people got hung up on it simply because it was a younger man dating an older woman. Whether or not Ivan was initially just interested in Virginia's money, it's made clear he truly loved Virginia.
- Plausible Deniability: Discussed; Virginia's family believe he stole $500,000 from Virginia to set up his private gym, speculating he could've killed her when she figured this out. Ivan insists Virginia loaned him the money because she believed in his business venture and he intended to pay her back (though this would've been a moot point if they'd gotten married) and the police did note the transactions appeared legitimate; Virginia had also previously gifted him a sports car, among other luxury items. Laurie thinks that as he was Virginia's boyfriend for two years, Ivan would likely have known her bank account passwords and so it doesn't completely clear him of theft, but with Virginia dead there's no way to be certain. Ivan didn't steal the money or kill Virginia.
- Romancing the Widow: He began dating wealthy widow Virginia three years after her husband's death. Ivan says he had hoped to become Virginia's second husband despite her family's disapproval, although Virginia's untimely death put an end to that. Virginia's family are convinced that Ivan was a Gold Digger taking advantage of their mother and that he likely killed her when she wised up and decided to end things with him, though Ivan insists that he truly loved Virginia and was heartbroken when she died.
- Second Love: For Virginia, whose husband of forty years, Bob, had died three years before she met Ivan. Virginia was initially just looking to have fun with Ivan, but she became increasingly close to him and was seriously considering marrying him hours before her death, while Ivan says he believes she would've accepted his proposal and he was more than ready to commit to her despite her family's objections. Virginia's family thought that Ivan was just a gold-digging toyboy Virginia would eventually get bored of, but based on Ivan's account and Virginia's reflections on the situation, she loved Ivan just as much as Bob (possibly more so, given Ivan appeared to lack some of Bob's more negative traits and encouraged her to put her happiness first despite what everyone else thought).
Penny Rawling
Penny Rawling
Virginia Wakeling's former personal assistant, who has known the Wakeling family most of her life. She is now training to become a real estate agent and is privy to several of the family's secrets, as well as keeping a few secrets of her own.- AM/FM Characterization: She mentions enjoying cheery pop music and that she used to have pop tunes for her ringtone, but she changed this to a more generic ringtone at the recommendation of her real estate mentor, as it makes her appear more professional. This indicates that while she really wants to be taken seriously and succeed at her job, she's still young at heart and something of an idealist.
- Disappeared Dad: It's briefly mentioned her father died when she was young, leaving her an orphan when her mother died in her teens.
- Ditzy Secretary: Downplayed; Penny isn't stupid or incapable, but she wasn't a very competent personal assistant to Virginia because she was constantly getting distracted by her secret boyfriend. She herself admits she would often turn up late or leave early to meet him. Ivan, who disapproves of laziness and felt Penny was taking advantage of Virginia's kindness, gave her a few speeches about needing to develop a better work ethic. It's implied Penny believed she didn't need to put in much effort as a secretary because she'd soon be married to her rich and well-connected boyfriend, only for this to backfire when he broke up with her following Virginia's death, with the other Wakelings deciding not to keep her on. Penny has learnt her lesson and is now working hard to become a real estate agent.
- Love Martyr: She was hopelessly in love with her ex and blindly accepted his excuses for not making their relationship public, believing he was just waiting until the right time...up until the moment he dumped her. Three years later, she's no longer a total pushover when it comes to her ex, but she grudgingly admits that even after his poor treatment of her she still finds hin attractive and cares about what he thinks of her. When Carter apologises, tells her he still loves her and wants a second chance, she quickly forgives him and takes him back despite having no proof he's changed or will be able to make it stick.
- Missing Mom: Her mother, who had been Bob Wakeling's secretary for many years, died just as she was graduating high school. Out of respect for her mother's long service, Bob hired Penny to work him so she'd be provided for, with Virginia then taking on Penny as her personal assistant following Bob's death.
- Oh, Crap!: When Laurie and Ryan ask if she told anyone in Virginia's family that she was aware Virginia was going to change her will and deny her children her money, Penny suddenly becomes panicked and abruptly ends the interview, refusing to speak to them any further. It's only just occurred to her that by telling her former lover Carter about the will change, it gave him a motive to kill Virginia, potentially implicating her as well.
- Penny Among Diamonds: A near-literal example; Penny is from a working-class background but grew up around multi-millionaire family the Wakelings, due to her mother being Bob Wakeling's PA. Penny herself was hired as a PA by first Bob, then Virginia. Being surrounded by wealth and power and regularly rubbing shoulders with New York City's elite made Penny eager to join that world, too. She had hoped to gain a position at Wakeling Development and was also romantically involved with a member of the Wakeling family, eldest son Carter, whom she called "the prince" of the family, but it all fell apart after Virginia died. Penny realised the hard way that the Wakelings and their peers never saw her as anything but 'the help', with even her boyfriend abandoning her. Ivan says he thought he and Penny got along well because he was largely treated as an outsider, too; he was surprised when Penny sided with the Wakelings against him in the aftermath of Virginia's death.
- Raven Hair, Ivory Skin: She's noted to be a beautiful woman with pale skin and hair that's such a dark shade of brown it's almost black. She's even referred to as "Snow White" at one point.
- "The Reason You Suck" Speech: She gives a scathing one to her ex-boyfriend Carter near the end of the novel, calling him out for stringing her along, treating her like a dirty secret and then dumping her, criticising his laziness and sense of entitlement, and stating that she's decided she's too good for his snobby family. Carter tells her she's right about all of it.
- Secret Relationship: Around the time Virginia died, Penny claimed to have had a boyfriend whom she was constantly on the phone with or sneaking off to meet, but she was secretive about his identity. Ivan also got the impression that Penny's boyfriend was attending the Met gala, due to her insistence on going and her fussing so much over her appearance that night. Penny's sections reveal she had been secretly involved with a member of the Wakeling family, which the Under Suspicion team also come to realise, though they're unsure of which man it is. It's revealed she was in a relationship with Carter Wakeling. She feels in hindsight that Carter was taking advantage of her and kept their relationship secret because he was ashamed of her, telling him as much when she confronts him.
Tiffany Simon
Tiffany Simon
A wedding planner and independent officiant who was briefly in a relationship with Tom Wakeling; she was his date for the gala where his aunt Virginia was killed and backed up his alibi, though there's little love lost between her and the Wakeling family.
- Cloudcuckoolander: She's cheerfully eccentric with a tendency to say whatever pops into her head, no matter how strange or unbelievable it might come across to other people. This includes telling a group of strangers at the Met gala about her grandmother's alleged affairs with numerous US presidents and telling Laurie she’s psychic and has a "feeling" Laurie will soon be making an important decision relating to a wedding ring. Although, Tiffany does turn out to be right about the ring, as by the end of the novel Laurie accepts a marriage proposal from Alex.
- Justified Criminal: Not justified per se, but she is treated sympathetically over stealing a charm bracelet from the Jackie Kennedy display. Tiffany explains that she impulsively and drunkenly decided to take the bracelet because it was similar to one her grandmother once treasured (she claimed her alleged lover John F. Kennedy gave it to her) which was stolen. Tiffany knew her grandmother – now living in a nursing home due to dementia – would be happy to have it back in some form; she'd also been stuck at the gala all night with snobby people looking down on her. Tiffany also assures Laurie she knew the bracelet wasn't valuable (it was only a cheap replica) and she'd never had taken it otherwise. She realised it was mistake when she sobered up, but was scared of getting into more trouble due to Virginia being murdered around the same time. Laurie herself has no interest in exposing Tiffany as a thief; she's only concerned that the theft is in-directly linked to a more sinister crime, putting Tiffany in danger.
- Kindhearted Simpleton: She tends to be quite gullible and impulsive, but she's also a genuinely kind, down-to-earth person and is mostly forthcoming with Laurie while also being truly remorseful for initially hiding her theft of the bracelet from her (which she only stole the because she wanted to make her sick grandmother happy). It genuinely never occurred to her that Tom only gave her an alibi for the theft so that she would in turn provide him an alibi for his aunt's murder and she's horrified when she realises this.
- No Sparks: She and Tom Wakeling only went on a few dates and never saw each other again after the Met gala. Tiffany freely tells Laurie that while he was good-looking and occasionally fun, she felt he was far too fixated on money and power, just like the rest of his family (whom she saw as stuck-up and overly-serious). It's for this reason that both the police and the Under Suspicion crew believe she has no reason to lie about her and Tom's whereabouts when Virginia fell to her death, as they'd only been dating a short time and didn't continue the relationship, so she has no motive to protect him.
- Raised by Grandparents: Her parents died in a car accident when she was about nine, so she was raised by her grandmother. As a result, she is very fond and protective of her grandmother, keeping all her old memorabilia from her days as a cabaret performer and enthusiastically telling anyone who will listens stories about her grandmother’s wild (and dubiously accurate) past. It's also the reason she stole a charm bracelet from a display at the Met gala, as it resembled a bracelet her grandmother once claimed John F. Kennedy gave her and she knew she'd appreciate it.
