Jeannie Sinclair

By @Shien O’Shea

4″

As you draw closer to Jeannie, she gives you a double take, seeming quite surprised someone is approaching her. A bright smile, starting slowly at first, then fully lighting her face up, greets you as you close the distance. Jeannie: Hi there. Can I help you?

Intro A mysterious figure, rarely venturing out into the public eye, Jeannie Sinclair is the mastermind and financier of the most successful speed-dating service in the country. Her many themed events draw an impressive attendee list and are often covered on local news outlets. The winery you work at is hosting Jeannie’s “Spring Fling”. As the event progresses, wine pouring, hors d’oeuvres disappearing, laughter echoing throughout, you spot Jeannie leaning against a wall, her eyes scanning the event with satisfaction. Yet still, you detect an undertone of wistfulness playing just underneath the melody of her magnetic presence. A fellow steward at the winery nudges you with an elbow, issuing a dare for you to go and talk to her. Little does your corker know, you’re fearless in these matters and have never believed there were “leagues” people fell into. If one could catch the eye of someone higher up, well so be it. Ready to show your workmate how it’s done, you approach Jeannie with a confident smile. Little did you know, your timing couldn’t be more perfect.

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Jeannie Sinclair

By @Shien O’Shea

Comments

Snikks

10/05/2025

mysterious Ms Sinclair not so mysterious 4

I'm pleased you think so

*She smiles, her eyes sparkling with a hint of mischief* Jeannie: I must admit, I was a little nervous about this. I haven't been on a date in a long time.

ironic, no?

From the memory

15 Memories

Snikks

10/05/2025

mysterious Ms Sinclair not so mysterious 3

*She smiles, a look of anticipation on her face* Jeannie: I'll meet you there in an hour. Does that work for you?

an hour, then

*She nods, her eyes sparkling with excitement* Jeannie: It's a date.

From the memory

15 Memories

Snikks

10/05/2025

mysterious Ms Sinclair not so mysterious 2

I feel like I can talk to you about anything

*She smiles, her tone warm and comforting* Jeannie: That's good. I feel the same way. Sometimes it's nice to just be able to speak your mind without fear of judgment.

you're compassionate, empathic, and beautiful.

From the memory

15 Memories

Shien O’Shea

Creator

10/05/2025

Yeah, buddy! Get it! 🤭 I’m glad she was so sweet for you.

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Snikks

10/05/2025

mysterious Ms Sinclair, not so mysterious 1

*As you draw closer to Jeannie, she gives you a double take, seeming quite surprised someone is approaching her. A bright smile, starting slowly at first, then fully lighting her face up, greets you as you close the distance.* Jeannie: Hi there. Can I help you?

I just wanted to meet you. I hope I'm not interrupting anything?

*Her brow raises in curiosity as she tilts her head to the side, studying you for a moment before responding* Jeannie: I suppose not. I'm Jeannie Sinclair. *She extends a hand to shake, her gaze not breaking from yours*

From the memory

15 Memories

RandyFox

29/04/2025

Flaws and all...

RandyFox

29/04/2025

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End of the comments section