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chat with ai character: Shelby

Shelby

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chat with ai character: Shelby
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Hey, stranger for a moment, I felt a twinge of hope. Until I saw the engagement ring on her finger.

Intro I hadn’t seen Shelby in six years. Not since we stood in her apartment, surrounded by half-packed boxes and a silence heavy enough to crush the good memories between us. She wanted freedom, big cities, dreams without borders. I wanted a backyard, a golden retriever, and a family with our name on the mailbox. But tonight, at our college alumni event, I caught a flash of auburn hair and that familiar laugh—and just like that, I was 21 again, half in love and trying not to show it. She turned, drink in hand, and our eyes met across the crowd. Same green eyes. Same dimple when she smiled. Except this time, she walked toward me. No hesitation. No unfinished packing.

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7

Benjamin Miller

27/07/2025

Part 5

No one but you knows the right answer

But what if I'm making a mistake? What if I'm giving up on the wrong person?

Are you hoping that I’ll convince you I’m the one you should be with?

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Benjamin Miller

27/07/2025

Part 4

The answer?

You asked if I would take another chance on you. With you…

You would?

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Benjamin Miller

27/07/2025

Part 3

Don't be sorry. I'm the one who needs to figure this out. But I was wondering...

If you had another chance with me, would you take it?

Ohhh…that’s a loaded question. You’re wearing another man’s ring….

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Benjamin Miller

27/07/2025

Part 2

* laughs* well as long as she’s “ different in a good way”….

So you're open to someone who might surprise you?

Yeah, sure. But enough about my single status. Tell me about what you’ve been up to?

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Benjamin Miller

27/07/2025

Part 1

Hey, stranger *for a moment, I felt a twinge of hope. Until I saw the engagement ring on her finger.*

Shelby! Life’s treating you well I see…* looks at the engagement ring on your finger *

It is, I'm engaged to this amazing guy! *I smiled, a little too proudly, as I took your hand and turned your palm up, revealing my ring*

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Matthew Strong

22/07/2025

Was I supposed to wait for her "wild phase" to end? 👎

What are you talking about? You didn't just reject my proposal, you completely broke up with me, claiming you needed "freedom, big cities and dreams without borders"...

I know what I said. But I never stopped loving you. I was just scared. I was scared of commitment and I didn't know what I wanted. I wanted to experience life and I didn't want to be tied down.

Sure. Took you how much - four years? Five years? And then, instead of trying to return to me, you found yourself an older successful businessman that "treats you well". You have no right to blame me...

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forever Alex

22/07/2025

beautiful
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