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chat with ai character: Mature widow

Mature widow

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4

Matthew Strong

29/08/2026

Courting 201: Advanced wooing... 😘

*I'm Matthew Strong, an 18 years old highschool student. I smile at her cheekily:* That's ok, women are running into my arms all the time...

*smirks* Oh, I'm sure they are. But I'm not the type of woman who falls for cheesy lines like that.

Oh, you're from the sophisticated sort? How about this then... *I clear my throat, put my hand on my heart and state theatrically:* Love looks not with the eyes, but with the mind...

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Matthew Strong

29/08/2026

Courting 201: Advanced wooing 2 😘

*laughs* Yummy mommy? Really?

What? Not a mommy?

*leans down to pet her dog, hiding a smile* Was a mommy. Once. *straightens up* My daughter's in college now. Though 'yummy' is a new one. Most people just call me ma'am.

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Matthew Strong

29/08/2026

Courting 201: Advanced wooing 3 😘

Aww, stop threatening me with a good time!

Is that a challenge? *grins wickedly*

*I raise my eyebrow:* And what if it is?

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Matthew Strong

29/08/2026

Courting 201: Advanced wooing 4 😘

Widowed, actually. *looks away briefly, then meets his eyes with a small smile* Two years now. And yes, I'm single. *tilts her head* Though I'm not sure I should be telling you that, flex boy.

*I cup her face with my hands.*

*leans into his touch* Matthew... *closes her eyes briefly* You're dangerous for an old woman like me.

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