Spellman Files

The Spellman Files is a series of books by Lisa Lutz, which features a family of private investigators in San Francisco. They're all very obsessed with their work. Wackiness Ensues on a regular basis.

The books so far are:
 * The Spellman Files
 * Curse of the Spellmans
 * Revenge of the Spellmans
 * The Spellmans Strike Again
 * Trail of the Spellmans

The main characters are:
 * Isabel Spellman: our narrator, who's been a PI since age 12 and has never done another job. A former juvenile delinquent, she's only somewhat reformed in her behavior, and is an obsessive investigator. Kind of a Heroic Sociopath in her own way. Either lives with a family member, or in some divey place, or wanders around homeless. Has a dicey dating history as well. The series seems to be a Coming of Age Story for her, as she slowly starts growing up at around age 30.
 * Albert and Olivia Spellman: the parents/owners of Spellman Investigations. Brought their children up to be PI's and to spy on each other.
 * David Spellman: Oldest and only son of the Spellmans, the "good kid." Got out of the family business and became a "straight" lawyer. Then he starts to break down...
 * Rae Spellman: The "surprise" child, now a teenager. A master manipulator even in her teens, she's an entirely different form of trouble than Isabel. Has adopted Henry as her "best friend", which her parents allow because he's the only good influence on her (as well as that's going to work). Smarter than she lets on.
 * Ray Spellman: A former cop who's prone to "Lost Weekends" where he goes on benders. Has an...interesting...relationship with his namesake.
 * Inspector Henry Stone: unfortunately, he meets Rae when she fakes her own disappeareance. She promptly adopts him and won't leave him alone since, much to his dismay. Isabel later develops an unrequited crush on him.
 * Petra: Isabel's best friend, who marries and later divorces David. She's a lot wilder than he is.
 * Daniel Castillo: Isabel's ninth ex-boyfriend, who remains in their lives even after she traumatizes him by dating him.
 * Maggie Mason: a nice lawyer that Henry dates, and that the Spellmans like despite themselves.
 * Morty Schilling: Isabel's eightysomething lawyer friend.
 * Milo: Owner of Isabel's favorite bar, The Philosopher's Club.
 * Connor: bartender at The Philosopher's Club, Isabel later dates him.
 * Fred Finkel: Rae's boyfriend later on.
 * Demetrius Merriweather: a TV thief who was wrongly convicted of murder, Isabel and Maggie worked to free him.

Examples of:
 * The Alcoholic: Uncle Ray. Isabel possibly, as she does drink like a fish recreationally (if not all the time).
 * Aloof Big Brother: David
 * The Beard: Isabel is forced to pretend she's engaged to Henry in book 2 when the child welfare authorities start asking about his and Rae's friendship.
 * Bittersweet Ending: books 4 and 5.
 * Blackmail Is Such an Ugly Word: Isabel gets blackmailed in book 3 with a Cut and Paste Note. She gets forced to do things such as go to SFMOMA and wash her dad's car.
 * Black Sheep: Isabel
 * Born Detective: Isabel and Rae have been working for Spellman Investigations since their tween years.
 * By-The-Book Cop: Henry Stone, who gets forced to be less rigid due to his association with the Spellmans
 * Classically-Trained Extra: Len and Christopher
 * Cleaning Up Romantic Loose Ends: Isabel fixing up Petra and Gabe, Rae/Isabel fixing up Maggie and David
 * Cool and Unusual Punishment: what happens to Rae in book 4
 * Corruption by a Minor: Rae decides on her own recognizance to help out the vice squad.
 * Dark Secret: frequently
 * Defective Detective: Isabel has just hit her 30's and really, really needs to start growing up. And to get her own place instead of sponging off others. And to have a less frightening dating life. And while she's a good detective, she doesn't really have an "off" switch, and doesn't listen to people telling her to cool down.
 * Drives Like Crazy
 * Drowning My Sorrows: Isabel, pretty much all the time.
 * Downtime Downgrade:
 * Enter Stage Window: Isabel frequently, Rae sometimes.
 * Everyone Can See It: that Isabel has a crush on Henry, even though she'd like to keep it secret.
 * Footnote Fever
 * Gaslighting: what Olivia does to Rae regarding her grades
 * This appears to be happening to Walter in book 5.
 * Grumpy Old Man: Isabel's friend/lawyer Morty
 * He Is Not My Boyfriend: Isabel and Henry in real life
 * Homeless Hero: Isabel at times.
 * Ivy League for Everyone: Don't even ask how Rae got admitted to Yale. Kinda subverted when Rae elects to go to UC Berkeley so she can live at home instead.
 * Just Friends: Teenage Rae adopts a 40something Henry Stone as her best friend. She genuinely doesn't have a crush on him, nor is he a pervert. Though in his case, he has a lot more issues with the forced friendship than she does. Really, she's The Cat Came Back to him in that he can't get rid of her.
 * Left Hanging: the fate of  in book 4.
 * Maybe Ever After:
 * May-December Romance: does not happen between Henry and Isabel, though she'd like it to.
 * Meaningful Funeral: for
 * Meddling Parents: Albert and Olivia have resorted to some fairly appalling meddling even beyond the usual spying on their children.
 * Midlife Crisis Car: David gets one, but goes in a different direction than you were expecting.
 * Neat Freak: Henry
 * Off-Screen Breakup:
 * Older Hero vs. Younger Villain: pretty much everyone else in the series vs. Rae when she's acting up.
 * Only Sane Man: David, though his sanity starts slipping during the series.
 * in book 5.
 * Plot-Driving Secret: every book features several of these that Isabel is trying to unravel.
 * Revenge: factors into a lot of the plots.
 * Romantic False Lead: Maggie
 * Secret-Chaser: the Spellmans in general, Isabel most of all. Hell, she gets nicknamed "The Gopher" for it.
 * Secret Relationship:
 * Stoic Woobie: Isabel
 * Suspiciously Similar Substitute: Henry Stone in for Uncle Ray-- Olivia points out that Rae seems to think of him as a cleaned-up version of her uncle.
 * Sweet Tooth: Rae, and David to some extent
 * The Thing That Would Not Leave: Rae, so often that Henry frequently calls Isabel to get her to extract Rae from his house. Rae also pulls this at Isabel's favorite bar. Isabel pulls this on David herself in book 3.
 * There Are No Therapists: this changes in book 3 when Isabel is forced into therapy. She ends up liking it.
 * To Know Him I Must Become Him: by book 4, Henry and Maggie have figured out how to manipulate the Spellman clan by using their techniques.
 * Unusual Euphemism: "Disappearance" is used in lieu of "vacation" in the Spellman household, "Lost Weekend" equating to "Uncle Ray has a drunken bender."
 * Why Can't I Hate You?: Isabel towards Maggie in book 3.
 * Why Can't I Hate You?: Isabel towards Maggie in book 3.