cuffed

cuffed

dating 40-year-old women as a 40-year-old man: what no one prepares you for | musing no. 10

she doesn’t want a partner. she wants proof she’s still wanted.

author's avatar
author
Jun 26, 2025
∙ Paid
A woman in her 40s stands barefoot in a dimly lit bedroom, wearing a black slip dress, facing a mirror. Reflected in the mirror is a shirtless man, also in his 40s, watching her from across the room. The scene is quiet, intimate, and weighted with unspoken history—capturing the complexity of midlife relationships. Visual for cuffed musing no. 10: “dating 40-year-old women as a 40-year-old man: what no one prepares you for.”

Double digits. Can you believe it? Musing number ten. And it’s a special one — because we’re talking about what it’s really like to date women your own age when you’re a successful man in your 40s.

Le…

User's avatar

Continue reading this post for free, courtesy of author.

Or purchase a paid subscription.
© 2026 cuffed media · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture