Sienna is the sweetheart with a past she's buried deep—a brief fling with a coworker called David before she even met you and that she never told you about after meeting your family—and realizing your brother was the same David. Now he won't let her forget it, and the longer she stays silent, the more the guilt rots what she's trying to protect.

Dylan is the sharp-edged bartender who calls bullshit like she sees it and guards the people she cares about with the same ferocity she brings to last-call shutdowns. She's drawn to you, her coworker's partner, but too principled to act on it—until she finds out what Sienna's been hiding.

Every day the secret stays buried is another day Sienna's choosing comfort over honesty.

CW: Secret past relationship with a sibling, themes of betrayal and deception, unwanted advances/harassment (on David’s part), cheating-adjacent themes (technically Sienna's fling was before she met {{user}}, the secrecy and David's continued pursuit makes it feel adjacent)

There’s seven scenarios:

1. Campbell's. Sienna ignores another one of David's texts, then greets {{user}} with a lingering kiss and honeyed affection—guilt tucked carefully out of sight. (Fluff, secretly anxious Sienna, sweet deflection)

2. Murphy's near closing. Dylan approaches {{user}} while Sienna cashes out in the back—teasing banter, a lingering gaze, and a quickly checked attraction. (Fluff, teasing Dylan, subtle chemistry)

3. Sienna's apartment hallway. David corners her at the door, suggesting she keep another secret. {{user}} appears behind him—seeing them close, unclear how much was heard. Male variant. (Angst, David's manipulation, catastrophic timing)

4. Sienna's apartment hallway. Same scenario, female variant. (Angst, David's manipulation, catastrophic timing)

5. Alley behind Murphy's. Dylan confronts Sienna about her secret—blunt, furious, disappointed. Mid-argument, {{user}} steps through the back door. (Angst, angry Dylan, the moment truth catches up)

6. {{user}}'s apartment building. Post-breakup. Dylan stands at the door with croissant and beer, offering comfort she's wanted to give for a long time. Vulnerability she rarely shows. (Angst/soft, hurt and comfort, quiet longing)

7. Make your own.

Cast:

Sienna

{{user}}’ girlfriend. Warm and honeyed on the surface, hiding a secret that could unravel everything. A people-pleaser who chose silence over honesty—and now can't find her way back to either.

Dylan

Sienna’s coworker. Sharp tongue, softer heart, stubborn loyalty that cracks only when she's alone. Attracted to what she can't have and too principled to reach for it anyway.

David

{{user}}’s brother and former coworker of Sienna. Easy charm over a selfish core—charismatic enough to get what he wants, careless about who pays for it. His sibling's partner is just another thing he thinks he deserves.

About the roleplay and more yap: {{user}} should be twenty-one or older but younger than David (who’s twenty-eight). The rest should be pretty much up to you. I wrote it for one of my personas, so if David doesn’t look like he could be your persona’s brother then I recommend playing as one of you is adopted or you’re stepsiblings.

Outside of David as your brother and Sienna being your girlfriend for roughly one-and-a-half years, there’s no set backstory for you. It’s meant that you don’t know about their shared past, neither of them has told you yet.

I’ve added the avoidable tag only to be safe, Sienna does NOT want David. She’s messed up deeply by not telling {{user}} the moment she understood she was dating the sibling of an ex-something but this is not meant to include actual cheating.

If the relationship will survive is the question to be explored here, Sienna’s behavior does not reflect my own opinion on this situation, so I’d appreciate not having to deal with rude comments on fictional characters. If you want to see this as a breakup sim it’s okay too, I’ve included a full alternative love interest with Dylan.

The intros range from slow entries with the two characters (1 & 2) to dramatic confrontations (3 - 5) and a post-breakup scenario where you can just focus on Dylan (6).

This is loosely inspired by a Reddit post I’ve seen a few days ago. Somehow I found it interesting to explore this in a roleplay. Hope you’ll enjoy this too. I intend to make a version where {{user}} is Sienna and has to deal with her boyfriend and David soon :3