Retail & Runway ™

Retail & Runway ™

Heartbreak & Hookups

Heartbreak & Hookups | Ch 17 | My Longest Relationship

Wasn’t with a man. It was with booze.

Darling Izzy's avatar
Darling Izzy
Oct 18, 2025
∙ Paid

The year is 1997. Imagine a goofy looking middle schooler with a crooked haircut and clips that pinned her uneven bangs. Chapped lips. Connected eyebrows. And a smile that could break your heart if you stared long enough.

Her fashion — curated from the local Indoor Swapmeet, K-Mart, and Mervyn’s.

The song that played on her boombox every night was My Boo by GhostTown DJ’s.

She spent her free time memorizing every lyric instead of doing her homework. Fantasizing about love and what lovers do while singing into a hair brush,

“…At night I think of you,
I want to be your lady, maybe.”

Somewhere between the pre-teen fantasies and family parties, she snuck a can of Budweiser into her grandmother’s bathroom, while luring her little cousin to join her.

*Insert the crispy sound of cracking open a cold one*

This post is for paid subscribers

Already a paid subscriber? Sign in
© 2025 The Hoodrat Company
Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture