Fated Mates S07.48: Con Artists & Criminals with Joanna Shupe

Podcast: Fated Mates – Romance Books for Novel People
Date: August 19, 2025
Guests: Joanna Shupe (also writing as Mila Finelli), hosted by Sarah MacLean and Jen Prokop

Episode Overview

This episode dives into the irresistible romance novel trope of criminals and con artists with special guest Joanna Shupe (also known for her dark romance as Mila Finelli). The hosts and Joanna explore why readers and writers are drawn to noble scoundrels, the enduring appeal of redemption arcs, and how these themes connect to class, justice, and the history of both the romance genre and society at large. The conversation also highlights Joanna’s latest historical novel, The Gilded Heiress, its first-person perspective, the challenges and complexities of writing about crime with empathy, and recommendations for more crime-adjacent romance reads.

Main Themes and Purpose

• The romance of crime: understanding why con artists, pirates, thieves, and mafia types appeal as romance heroes.
• Social justice and history in romance: how exploring crime allows authors to interrogate systems of power, class, and morality.
• Joanna Shupe’s writing process and her experience writing as both herself (historical) and Mila Finelli (contemporary, mafia).
• The importance and difficulty of integrating real history, especially marginalized histories, into historical romance.
• Craft talk: writing first-person historical, world-building, and managing reader expectations around "historical accuracy."
• Favorite sub-tropes: blackmailers, Robin Hood-types, con artists with a code, and noble criminals.
• A robust book rec section for those seeking more "criminal" romance leads.

Key Discussion Points and Insights

Joanna’s Dual Career and Reader Demographics

Timestamp: 02:02–04:15

• Joanna Shupe (historical romance) and Mila Finelli (mafia romance) write for largely distinct audiences.
• Finelli readers: tend to be younger, international; Shupe readers: more American and slightly older.
  "There's not a lot of overlap between the two reader groups... Mila people skew a little younger, I have a lot of readers from other countries... Shupe feels maybe not as international and a little older." — Joanna, 03:06

The Allure of the Criminal Heroine/Hero

Timestamp: 04:30–07:47

• Both Sarah and Joanna are passionate about the criminal archetype: con artists, mafia bosses, scoundrels, and the trope of redemption.
• Key appeal: seeing morally grey characters achieve redemption and challenge societal structures.
• Difference in writing historical vs. contemporary criminals: contemporary demands more realism, while historicals allow for "wackiness," but both leverage crime for power dynamics and noble causes.

Shades of Grey: Crime, Cops, and Justice in Romance

Timestamp: 07:47–09:51

• The binary of "good cops/bad criminals" is increasingly dismantled in romance.
• "The more you see of the world, you know that there are 'good people' doing bad things... there really is nobody who is above corruption." — Joanna, 09:29
• Historical and contemporary crime are often tools to discuss who gets to make or break the rules, and why.

Historical Romance as Political and Social Commentary

Timestamp: 10:05–18:23

• Joanna’s newsletters and social media often contextualize current events within historical patterns (tariffs, immigration, reproductive rights, Jim Crow, etc.).
• "What is happening today has happened before... watching your videos makes me always feel like, okay, we've been here before. Maybe we can survive it?" — Sarah, 10:41
• The podcast critiques education systems that erase marginalized histories, emphasizing a responsibility in romance to surface these truths.
• Joanna and the hosts lament the potential decline in historically rigorous romance, citing how books can teach vital, untold histories.

The Gilded Heiress: Class, Crime, and Found Family

Timestamp: 18:23–36:14

• Joanna discusses her new historical, The Gilded Heiress: an Anastasia-inspired, found family adventure featuring two lower-class protagonists—a streetwise con man and a talented orphan singer.
• Focused on class, revenge, and family rather than overt political commentary, but still unavoidably grapples with injustice and class stratification.
  "I was like, okay, we are NOT writing anybody who is titled. We're not writing anybody who is rich. Usually with every book, there's a deep issue, and this one I just wanted to write adventure... but wealth and class are always there." — Joanna, 18:23 & 19:27
• Leo, the hero: becomes a con artist to support his sisters after his family is destroyed by false accusations and lack of a social safety net.
• The dynamic: noble criminals are redeemed by their code, especially when “punching up" at corrupt or wealthy adversaries.

Writing Craft: First-Person Historical Romance

Timestamp: 36:25–43:41

• The Gilded Heiress is unique as a first-person, dual POV historical—a rarity in the genre.
• First person allows deeper access to the hero's justification and mindset, potentially making con artist actions more forgivable to readers.
• Challenges: ensuring the voice is authentic to the historical period without alienating modern readers (“the Tiffany problem,” period slang and language vetting). “First person as a voice just requires a kind of world building.” — Jen, 42:45

The Appeal and Moral Boundaries of Criminal Romance Leads

Timestamp: 54:19–58:30, 83:00–83:18

• Favorite criminal types: blackmailers, con artists, jewel thieves, pirates, avengers, “competence porn" experts.
• The noble criminal is defined as always “punching up,” defecting from corrupt systems, and protecting their own.
• Readers and authors have personal lines—is it property crime, noble purpose, or crimes against vulnerable people? Too much crime, especially against the heroine, is a dealbreaker.

Recurrence and Subversion: Women as Con Artists

Timestamp: 65:07–68:07

• Celebrates romances with lady con artists, fake mediums, and women working together in subversive crime.
• Highlights examples from Joanna Shupe herself (Baron), Kelly Bowen, and Cat Sebastian.

Broader Book Recs & Romance Lineage of the Noble Scoundrel

Timestamp: 54:15–68:00

• Shout outs to K.J. Charles’s An Unseen Attraction, Cressley Cole’s The Player, Jenny Crusie's Faking It and Welcome to Temptation, Kerrigan Byrne’s revenge-laden historicals, Elizabeth Hoyt's Duke of Sin, Beverly Jenkins, and many more.
• Distinction: Some classic romance authors (Julia Quinn, Julie Garwood) never write criminals, while others (Jude Deveraux, Joanna Lindsay, Beverly Jenkins) excel at it.
• Highlights how, for marginalized characters (e.g., in Beverly Jenkins’s work), breaking the law is less about rebellion and more about survival and retelling history from the margins.

Memorable Moments and Quotes

• On criminal heroes:
  “There's very few people in the industry who love a criminal the way you and I love a criminal.” — Sarah [04:51]
• On morality:
  “There is nobody who is above corruption.” — Joanna [09:29]
• On class and justice in The Gilded Heiress:
  “There's no pension, there's no retirement... there's no social safety net. So this is why Leo becomes so forgivable as a con artist.” — Sarah [31:57]
• On writing:
  "Writing it in first person allows you to get away with things because you're in the criminal's head and they can justify what they're doing..." — Joanna [38:11]
• On worldbuilding:
  “First person as a voice just requires a kind of world building.” — Jen [42:45]
• On noble criminals:
  “These criminals in a romance novel have to punch up, for sure.” — Sarah [58:08]
• On genre divides:
  “Some people write criminals and some people don't.” — Jen [77:39]

Important Timestamps

• 02:02–04:15 — Joanna on reader groups and their differences.
• 04:30–07:47 — The enduring appeal of criminal leads.
• 10:05–18:23 — Romance as a vessel for historical education and political consciousness.
• 18:23–36:14 — The Gilded Heiress: premise, class, and motivation.
• 36:25–44:07 — First-person historical writing: challenges and advantages.
• 54:19–58:30 — Ranking favorite criminal types, the code of the scoundrel.
• 65:07–68:07 — Women as con artists in romance: highlights.
• 83:00–83:18 — Where authors (and readers) draw the line on criminality.

Book Recommendations from the Episode

• The Gilded Heiress by Joanna Shupe (historical, first-person con artist/Anastasia retelling)
• Baron by Joanna Shupe (fake medium heroine)
• Faking It and Welcome to Temptation by Jenny Crusie (con artists, family cons)
• Kerrigan Byrne’s historicals (revenge-driven criminal heroes)
• Duke of Sin by Elizabeth Hoyt (blackmailer hero)
• A Good Rogue is Hard to Find by Kelly Bowen (lady con artists/Robin Hood companions)
• The Perfect Crimes of Marion Hayes by Cat Sebastian (woman on the run, blackmailer/highwayman hero)
• Hidden Sins by Selena Montgomery/Stacey Abrams (con temporary, hidden grifts)
• The Player by Cressley Cole (noble-purpose thief)
• An Unsuitable Heir by K.J. Charles (revenge-fueled theft)
• The Windflower by Laura London (old-school pirate/scoundrel epic)
• Annual Diamonds by K.J. Charles (family-focused heist)
• The Unwanted Wife by Natasha Anders (blackmail, marriage in trouble)
• Private Arrangements by Sherry Thomas (marriage in trouble, leverage)
• Destiny’s Captive & Captured by Beverly Jenkins (con artist and pirate heroines)
• To Catch a Raven by Beverly Jenkins (female con artist, Declaration of Independence heist)

Notable Segments

• The Lindbergh Baby & Anastasia Mythos — Origin of The Gilded Heiress inspiration, mixing historical cases and reinventing classic lost heiress stories. [48:40–53:12]
• Pirates and shifting romance subgenres — Pirate romances have faded due to historical context (slave trade); now, the focus is more often on smugglers and con artists. [56:02–57:44]
• Lady Con Artists — Special callout to women "doing some crimes together." [68:00]
• Book Tour Details — Joanna promotes a multi-city tour, including stops with other romance authors. [84:15–86:43]

Conclusion and Tone

The discussion is feisty, humorous, and passionate, true to Fated Mates’ lively, insurgent take on the genre. Joanna Shupe and the hosts are unapologetically enamored with the criminal hero, but also deeply thoughtful about the social and historical resonance of these stories. The episode is packed with recommendations, behind-the-scenes writing craft notes, and ample encouragement for listeners to dig deeper into both the fun and the substance of romance fiction.

For the full book rec list, further history, and links, visit the show notes at Fated Mates’ website.