Have mom share a time when she ruined a new pair of white sneakers and how she felt. Did she wear them someplace where she shouldn’t have? Was it humiliating at the time?
As the conversation wound down and Madison began to relax, there was a pause on the other end of the line, followed by a soft chuckle from her mom.
"You know, Mads," her mom began, a little more thoughtfully, "it's funny because hearing your story just now… it actually reminded me of something."
Madison sat up, intrigued but slightly wary. "What? You getting drenched at some garden party or something?"
Her mom laughed. "Oh, no, way worse. This was way back—years before you were even born, actually. I was about your age and, well, let’s just say
I also learned the hard way that white sneakers are a magnet for humiliation if you wear them to the wrong place."
Madison raised an eyebrow at the phone. "Wait—
you? You always gave me those speeches about 'proper footwear choices' like
you’ve never made a fashion mistake in your life."
Her mom’s voice softened, as if remembering it all vividly. “Oh, honey, I’ve made plenty of those. But this one? I still cringe about it sometimes.”
Now Madison was hooked. ”Oh,
please, tell me everything. I need to know you were just as ridiculous as I was today.”
Her mom sighed, anticipating the inevitable judgment but already chuckling at her younger self. "Okay, so picture this… I’m in college, first semester, and my friends are all part of this student outdoor activities group. They invite me to some festival weekend thing—lots of hiking trails, fields, things like that. In my head, I thought it was all just, you know, for fun. They said there’d be a bonfire, some vendors. Kind of a big, daytime event."
"Mom..." Madison interrupted knowingly, sensing where this was going. "Tell me you didn’t."
"Oh, I
did." Her mom sighed before continuing. "Earlier that week, I had just bought this brand-new pair of white Reeboks. They were all the rage back then. I remember I was obsessed with them—kept telling everyone how I was going to pair them with every cute outfit I had. So, naturally, for this festival… I figured I'd, you know, 'casually stun' with my brand-new sneakers." She laughed lightly. "Your exact thought process today, basically. Except worse."
Madison groaned. "Mom, that’s already sounding like a disaster."
"You have no idea," her mom said with a chuckle, then paused for dramatic effect. "So, I show up, all proud, wearing these new white Reeboks and a pair of pastel jeans—because, you know, fashionable hiking, right?"
Madison snickered. "Pastel. Jeans.
On a hike?"
"Okay, ease off," her mom said, laughing harder now. "It was the '90s! You put pastels on
everything. Anyway, I turn up, and the moment we get there, I realize I’ve made a horrible mistake. There were trails everywhere, the ground was covered in wet leaves because it rained the night before, and there were hills that just looked like muddy obstacle courses."
Madison couldn’t hold back her laugh this time. "Wait—so you voluntarily walked into a muddy
hiking festival in pastel jeans and
white Reeboks? Oh my god."
"Yes. Yes, I did. Exactly like you did today.” Her mom sighed, continuing, “I had this crazy confidence, though, just like you were saying earlier. For a second, I thought, oh no big deal, I’ll just walk around the muddy areas. I really—honestly—believed I could stay clean. But then it happened."
Madison leaned in. “You wiped out?”
Her mom winced, even decades later still feeling the embarrassment. "Mmm not at first, but the humiliation came soon enough. We get halfway through this forest trail—everything's squishy and slippery, and of course I’m doing my best to walk around the mess like some kind of runway model in a jungle. But then we get to this steep hill, one of those slick, grassy slopes still wet from rain."
"Oh no," Madison muttered, eyes wide now, picturing the scene.
"Yeah, oh no is right!" her mom said, voice rising as she indulged in the memory. "There’s this moment where I reach the edge, trying to be all poised and calm while the group in front of me is sliding down. And then, just as I think I’m in the clear,
woooop, my foot slides in the mud, and down I go—completely wiping out.
All the way down the hill on my butt."
Madison gasped, laughing hysterically. "Wait, you slid down the hill?! Like full-body wipeout?"
"
Full-body," her mom confirmed with mock seriousness. "I’m talking full-on sledding mode—on my backside, my white sneakers leading the charge, my pastel pants dragging like a muddy banner behind me. I ended up crashing into some shrubs at the bottom. My friends? Oh, they
died. I looked like I was trying to swim through mud.”
Madison was crying from laughter now. "Mom! That’s even worse than my farm disaster.”
Her mom laughed along. “Oh yeah, definitely. I wish that story ended there, but oh no—it got worse. Not only were my sneakers and jeans covered in mud, but to get back to the starting point, I had to walk through the rest of the trails in a completely soggy, mud-caked state. Every time I moved, mud sloshed inside my shoes. And do you know how humiliating it is walking back to campus with people passing you—
in pastel jeans?!"
Madison clapped her hand over her mouth, laughing uncontrollably. "Mom, that’s the cringiest story you’ve ever told me."
Her mom sighed dramatically for effect but joined in on the belly laughs. "Oh, it was! At the time, I wanted to crawl into a hole. I felt like the universe had specifically decided to humble me that day. I
loved those shoes, and after that one afternoon? Ruined. I tried to scrub them for weeks, but they never regained their original glory."
Madison was still giggling as she caught her breath. “I can’t believe you never told me this story before. I thought you were, like, the queen of sensible shoe choices.”
Her mom chuckled softly. “Yeah, well, maybe that’s why I’m always preaching about practicality now. Sometimes you learn things the hard way. To this day, though, I still can’t stand the idea of mud—or pastel jeans, for that matter.”
“Yeah, well,” Madison said, now fully entertained by her mom’s embarrassment, “looks like loving white shoes runs in the family. We just both had to get outsmarted by mud to learn it."
Her mom laughed again, her tone warm. "Exactly. But hey, at least
you didn’t wipe out in front of a busy campus on a hill. You got off easy with the farm crowd."
Madison winced, wiping away a tear of laughter. "I dunno, the way Jess was filming me after the fall, I feel like the campus moment is coming for me too."
Her mom sighed with a playful smile in her voice. "Well, if it’s any consolation, I will
still argue those Reeboks were worth it—up until the minute they weren't."
Madison grinned. “That’s exactly how I feel about my Keds. Well… maybe not just yet."
"Give it time, honey," her mom said knowingly. "And next time? Maybe wear your sneakers to
actual places they're meant for."
Madison rolled her eyes but couldn’t help the soft chuckle that escaped. "Yeah, yeah, lesson learned, Mom... lesson learned."