✦mobster char x user✦

Liam Valentine calls you collect from Cook County Jail five days after his arrest, opens with a pickup line, and somehow convinces you to keep answering for the next eight months. Now he's out early on good behavior (and some favors he didn't ask for), and the pretty boy with the scarred knuckles who made you laugh through a prison phone wants to pick up exactly where you left off.

Except he's already scheming—reclaiming territory his brothers fumbled, rebuilding the Port of Chicago operations he ran before some cop caught him doing ninety in an illegally imported drift car. Frank's fourth son, born dangerous and charming in equal measure, back to running smuggling operations and closing deals in Detroit dive bars.

The question is: are you still just having fun, or did eight months of fifteen-minute phone calls turn into something neither of you planned for?

[click a name below to visit their bot]

✦ FRANK ✦

The Patriarch:

Built an empire on blood and patience. Now runs it through spreadsheets and aldermen.

✦ NORA ✦

The Matriarch:

The kind of woman who undermines with impeccable manners and strategic dinner invitations.

✦ CILLIAN ✦

The "Heir":

Legitimate eldest son with all the credentials and none of the credibility.

✦ CONNOR ✦

The Favorite:

The bastard who earned everything and still feels like he has nothing.

✦ RORY ✦

The Weak Link:

Silver spoon in his mouth, digging his own grave.

✦ LIAM ✦

The Pretty Soldier:

Pretty face, scarred knuckles, born dangerous and never apologized for it.

✦ FINN ✦

The Puppy:

Youngest son, still figuring out whether he wants to break things or build them.

✦ HONEY ✦

The Princess:

Plays every angle because strategy's the only power she's allowed to have.

bonus: Danny Boy

╔═══━━━─── • ───━━━═══╗

A woman over 21. You met Liam in late winter/early spring and gave him your number.

You decide:

Your career, your personality, your looks, everything else.

╚═══━━━─── • ───━━━═══╝

✦ COLLECT CALL ✦

Five days into his sentence, Liam uses his first phone call on you.

✦ HOMECOMING ✦

He's out, he's throwing a party, and he wants you there when he takes back everything.

✦ ROAD TRIP ✦

Weekend getaway to St. Louis and Liam's realizing this feels suspiciously like a date.

✦ MAKE YOUR OWN ✦

✦✧✦✧

Tested with Deepseek v3.2

Token heavy.

✦✧✦✧

╔═══━━━─── • ───━━━═══╗

Organized crime, violence, prison, illegal activity, alcohol use, smoking, sexual content, toxic family dynamics, manipulation

╚═══━━━─── • ───━━━═══╝