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Characters / Speakeasy Tonight

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NOTE: Due to the episodic nature of the game, this character sheet is under construction and may not be up to date.

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The Player Character

    Player Character 

Player Character / Heroine / Main Character ("MC")

Age: 19
Height: 5'2"

The player character. Born and raised in Columbus, Ohio, her parents send her to stay with her Uncle Charlie in Chicago in an attempt to straighten her out. Things... don't quite go as planned.

  • All Girls Want Bad Boys: Should you choose to pursue Vince or Gerald.
  • Closet Key: Sofia is this to her in her route.
  • Cool Big Sister: To her younger sister, Hazel. She used to have one in her older sister, Edith, but they drifted apart after Edith’s marriage.
  • Damsel out of Distress: Even though she might need help sometimes from the boys, she hates to think of herself as a girl who needs to be protected and In some routes, like Vince's and Neil's she learns how to shoot a gun. And in Neil's route she's not scared when Louis is threatening to kill her, or doesn't let Neil keep her out of a fight. She likes to think of herself and act as a modern woman.
  • The Flapper: Duh.
  • Hello, [Insert Name Here]: Her name is determined by the player.
  • Heroes Want Redheads: It's dyed, however.
  • In-Universe Nickname: The Ice Box Flapper.
  • Single Woman Seeks Good Man: If you pursue Cliff.
  • Took a Level in Badass: At the beginning of the story, the worst crimes she's committed are sneaking out to drink illegal alcohol at a party and dying her hair. By the end of a route, she'll have done a hell of a lot more than that.

Love Interests


Vince Moretti

Age: 26
Height: 6'

Vince is always in the thick of the action... especially because he incites half of it! While hot of the trail of Uncle Charlie’s shooter, you might get burnt if you get too close... but it would be so worth it.


Cliff Conway

Age: 27
Height: 6'

Cliff is The Face behind the speakeasy bar. His easygoing nature makes him a confidant of many secrets, as he always has an ear to lend to listen to your woes. His impressive boxer’s physique keeps the riff-raff away, but as bartender of an illegal establishment, he might be harboring a darker side himself.

  • The Bartender
  • Doorstop Baby: Left on the steps of an orphanage as a baby.
  • Genius Bruiser: Can carry two boxes of liquor on his shoulders with ease. Also an avid reader and wannabe writer.
  • Heterosexual Life-Partners: With Vince.
  • Make It Look Like an Accident: His other job for Charlie.
  • Nice Guy: One of the nicest guys in Chicago. Which makes the revelation that he’s the gang’s clean-up guy so surprising.
  • Parental Abandonment: His mother abandoned him when he was a few days old, and no father ever came looking for him.
  • Real Men Cook: Makes a mean rhubarb pie.
  • Inside Job: He is responsible for hanging up bodies and disguising the murders as suicides. In his route, Donovan investigates the strange suicides, and finds out Cliff is the one behind it. He doesn't kill anyone, though, he's just the clean-up man.


Neil Dresner

Age: 32
Height: 6'1"

A Tall, Dark, and Snarky Ice Box regular, and the gang’s go-to doctor when things go pear-shaped.


Donovan Gallagher

Age: 25
Height: 5'11"

Born in Dublin, Ireland. Donovan is a regular at the Ice Box and besides being a cop he is one of the officers on the payroll of Uncle Charlie. His job is to keep the Ice Box in the dark, protected from the Prohibition officers

  • Becoming the Mask: He's initially only interested in the MC to get Vince ticked off. What he didn't expect was actually falling in love with her.
  • Berserk Button: Don’t mistake him for a Brit.
  • Dirty Cop: Subverted. While he does take bribes from the bootleggers to look the other way, he's not a bad man, and does his job fairly well.
  • Fair Cop
  • Interservice Rivalry: The fastest way to tick him off is to bring up the Chicago Fire Department.
  • Oireland: Speaks with an accent that gets thicker the more he drinks.


Julius Harper

Age: 22
Height: 5'11"

The Ice Box bandleader and pianist, Julius likes to pass the time between sets reading poetry.


Elliot Graham

Age: 24
Height: 5'8"

A world-famous motion picture actor, Elliot is a handsome gentleman who unknowingly invites the MC to the Ice Box on her first night in Chicago. While not a member of Charlie’s gang, he plays the important role of drumming up business for the Box.

  • Accent Slip Up: When really angry or startled, his old country accent slips out.
  • The Charmer
  • Chick Magnet: Often arrives at the Ice Box accompanied by a number of women.
  • Dark and Troubled Past: When one of the girls he slept with realized her relationship with her wasn't going to be something more, she committed suicide. It's what led him to Uncle Charlie and had him help cover it up.
  • The Gambler: Very good at poker.
  • In-Universe Nickname: Elliot is known for his roles in famous romance movies, which earned him the nickname "The Great Lover."
  • Stage Name: He's actually a country boy and his real name is Amos Horton.


Gerald O'Fallon

Age: 27
Height: 5'10"

Gerald, the boss of rival speakeasy The Broiler, is charming, calculating, and can convince anyone of anything. Gerald will do whatever it takes to get what he wants. Not particularly invested in keeping grudges for grudges' sake, he’s willing to bide his time and be polite even with someone he hates (like Vince) if he can get something out of them (like booze).

As for honest work— it doesn’t suit him. He watched his parents break their backs and spirits with honest work, all for nothing, and he swore he’d be nothing like them. Gerald is only loyal to three people: himself, and his two sisters.

A recurring side character in the original release, he was Promoted to Love Interest in the Lovestruck Updated Re-release.


Sofia Martinez

Age: 23
Height: 5'3"

Sofia’s parents immigrated to Chicago from Mexico — where they were a middle-class family — to escape the revolution. An adrenaline junkie, she loves the adventure and thrill of being an informant, and living a fast life full of excitement, glamour, and danger.

Romantically and sexually, Sofia prefers women. While social mores dictate that she has to be discreet, she is very flirtatious when circumstance allows. Before you, her love life had been a series of passionate, short-lived affairs — generally her love burns hot and fast. Will you be the one to show her love can last forever?

Not present in the original version, she is a new character added for the re-release.

  • Action Girl
  • Ambiguously Bi: On the list of LGBT+ characters posted by the official Lovestruck tumblr, Sofia is listed as bisexual, but in her route she indicates that she only likes women.
  • Amicable Exes: She and Vince don't bear each other any ill-will for their failed relationship (in Sofia's case, mainly because she was never interested in men anyway), but they certainly butt heads enough over things to strain the word 'amicable.'
  • The Beard: Barney, who is also gay. After the protagonist convinces her to try something permanent with her and she breaks things off with Barney, Elliot happens to mention that Barney is working on a new script with his 'friend'; the protagonist assumes this means that he's got a sweetheart of his own to go back to, too.
  • Closet Key: For the protagonist. She does realize, however, that she did have some very close friendships before she met Sofia, so she probably wasn't the first girl she had feelings for altogether.
  • Commitment Issues: Never stays in a relationship longer than three months, because she knows that, because of the way society treats lesbians, it can't possibly last, and she'd rather end on a high note than a low one. The fact that the protagonist completely disagrees forms the main conflict of her route.
  • Contractual Purity: Specifically cites that there are 'morality' rules when it comes to stars nowadays, which is why she and Barney teamed up to use one another as Beards and still find success in Hollywood.
  • The Flapper: Once again, duh.
  • Gay Option
  • Guile Hero: Prefers to get her information through manipulation and skullduggery, rather than knocking heads like Vince, but is also more than capable of whipping out a pistol if the situation requires.
  • In Harm's Way: Loves the thrill of gangster life. However, after a particularly harrowing encounter, she claims that she's ready to give it up and move somewhere safer. The other characters note that this isn't like her at all, correctly deducing that something else is up.
  • Ladykiller in Love: Admits that she always tried to keep her girlfriends separate from her work, which is why she was always able to leave them. Not so with the protagonist.
  • Like Brother and Sister: She and Vince, whom she used to date, until she realized that she didn't want to date the gang, she wanted to be it.
  • Lipstick Lesbian
  • Pragmatic Pansexuality: Sofia is primarily interested in women (contradictory Word of God statements have her listed as both lesbian and bi) but she flirts with anyone who might help her gather information, and practically speaking that usually means men.
  • Spicy Latina
  • Working with the Ex: Her and Vince.


Other Characters

    Uncle Charlie 

Uncle Charlie

The player character’s paternal uncle.


Cleo Mayfield

Singer in the house band. Also MC's best friend.



The Ice Box doorman and bouncer.


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