It's The Roaring '20s. After being caught after returning home from a party by her parents, the player has been sent off from the country to Chicago, the heart of trouble. Seems like a bad choice, but she's been sent to live with her Uncle Charlie, who is supposedly a good man.
But he's not who you think he is. By some stroke of fate, you discover he runs a speakeasy known as the Ice Box behind his hardware store! After spending a night of fun at the Ice Box, news hits home that Charlie has been shot.
After explaining how you discovered the Ice Box to Charlie, he says he'll be out of commission for a while. You volunteer to run the Ice Box in his absence, and he agrees after much convincing. He leaves the Ice Box to you under one condition: you have one of his associates watch over your work.
And thus, your story as the Ice Box Flapper begins. Get ready to dive into a world full of booze, hot jazz, and even hotter men!
And who knows? Maybe that associate you're working with might just fall in love with you!
Your choices consist of:
- Vince, the smooth-talking bootlegger
- Donovan, the dirty cop
- Julius, the colored jazz musician
- Cliff, the bartender
- Elliot, the famous movie actor
- and Neil, the mob doctor.
The original app closed at the end of 2016; a new version of the game was subsequently released as part of Voltage USA's Lovestruck app, promoting rival gangster Gerald O'Fallon to love interest and adding a new love interest: Sofia, a singer at the Box and informant for the gang.
Speakeasy Tonight contains examples of:
- '20s Bob Haircut: The protagonist and Cleo sport fashionable period haircuts. Having cut her hair short is one of the things that marks the protagonist as a flapper, and is remarked on in the prologue when she arrives in Chicago.
- Affectionate Nickname:
- Vince calls the MC "doll".
- On Gerald's route, he starts calling her acushla.
- On Sofia's route, she calls the MC "bonita".
- All Girls Want Bad Boys: The MC on Vince's route.
- Becoming the Mask: In Donovan's route, 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: Vince is real easy to tick off, especially if Charlie or the MC gets hurt. According to Cliff, Vince gets this look in his eye known as that "red fog".
- He also gets ticked when he discovers anything connecting to his parents being killed.
- Big Damn Heroes: Donovan at the normal end of Vince's route.
- Butch Lesbian: Freddie, a Mole in another gang who serves as an informant for Sofia.
- The Charmer: Vince and Elliot are this.
- Childhood Friend: Vince and Cliff, since they were both raised in the same orphanage together.
- Dangerously Short Skirt: Discussed when the protagonist and Cleo go shopping and Cleo rejects one possible outfit for being a little too dangerously short.Cleo: "There's a fine line between 'sass-with-class' and 'shows-her-ass'."
- Dark and Troubled Past: Most of the guys have it.
- For Vince, his parents were killed when he was a kid. The only clue he has is that the killer had a tattoo of Medusa on his wrist.
- For Neil, he let his best friend die in war and became a morphine junkie. It got so bad that he had to break things off with his fiancé, who happens to be his best friend's sister.
- For Julius, he killed a guy that tried to force himself onto his sister, and they had to flee New Orelans because he knew the justice system would be biased against a person of color.
- For Elliot, when one of the girls he slept with realized her relationship with him wasn't going to be something more, she committed suicide.
- Dead Person Conversation: Neil is haunted by his friend's death so much that he hallucinates him every now and again.
- A Father to His Men: Charlie is well liked by all his associates.
- The Flapper: The protagonist's forays into the flapper scene are what prompted her parents to ship her off to stay with Uncle Charlie in the first place, and she's free to embrace the liberated lifestyle while she's running the Ice Box.
- The Gambler: Along with being a good actor, Elliot is very good at poker.
- Gay Bar: Sofia has a favourite lesbian bar she likes to hang out in. Interestingly, it's not just about pleasure - it also makes a great place to meet up with one of her informants, as unspoken agreements about privacy mean that nobody else there would blab about seeing them there together.
- Gayngst: In an interesting way. Neither the protagonist nor Sofia is particularly upset about being non-straight - when the protagonist first figures it out, she's mainly just overwhelmed and not sure of what she's doing - but Sofia is very aware of how difficult it would be for two women to really be in a long-term relationship, especially if she succeeds in becoming a movie star like she plans.
- Gay Option: Sofia
- Gender Flip: In-Universe, in Sofia's epilogue, a Hollywood friend of hers decides to make a movie based on the events of the route - but turns Sofia's character into a man. Sofia is pretty annoyed (mainly because she thinks all the best roles go to men), but Elliot notes that, given the relationship between her and the protagonist, they couldn't exactly have reproduced the story faithfully...
- In-Series Nickname: Elliot is known for his roles in famous romance movies, which earned him the nickname of "The Great Lover".
- The MC is known around Chicago as the Ice Box Flapper.
- Interface Spoiler: Defied in Sofia's route: part-way through, the protagonist meets an ex-girlfriend of Sofia's, but since she isn't given a sprite, the audience is lead to believe she isn't important. When the women plan their final infiltration, she comes back, as she currently works at the building they want into, and they need her to supply a key.
- Romantic Runner-Up: Vince develops feelings for the protagonist in Donovan's route, but she puts an end to their flirting once she realizes that she's serious about Donovan.
- Secret Keeper: In Sofia's route, Elliot finds out about the two women's relationship, but is completely okay with it and immediately promises to keep it a secret - as an actor, this isn't the first time he's encountered this kind of thing.
- Secret Relationship: Sofia and the protagonist, for obvious reasons.
- Shell-Shocked Veteran: Neil is a veteran of the Great War, and it's done a number on him.
- Took a Level in Badass: The protagonist in several of the more action packed routes.
- Most notable in the best end of Vince's route, where she manages to set the hideout of Charlie's shooters on fire.
- Woman Scorned: Sofia has a lot of angry exes. Luckily, none ever go beyond spitting fierce words at her and the protagonist, but it's enough to make the protagonist pretty concerned for the future of their relationship anyway.