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The original was posted on /r/tifu by /u/Radiant_Afternoon916 on 2025-04-26 12:48:13+00:00.
Met a really nice, successful guy recently. We planned a fancy-ish date. I wanted to look put-together and effortless, you know? Naturally, the universe said: Not today, Satan.
Morning of the date, I realized all my flats were either packed away or destroyed by a previous mud-related incident. Panic mode: activated. Mom offers me her boots. In a rush, I grab them without a second glance, trusting the process. (Mistake #1.)
Arrive at the venue. Big, upscale place. The guy’s running about 5 minutes late. I get up to move towards the center point and… THUD.
Everyone turns. I look down. My entire sole has fallen off. Like a dead fish flopping across the floor.
Cue instant fight-or-flight. I text him explaining there’s a “shoe emergency” (whatever that means) and plan to sneak out, buy shoes, and return looking flawless. But he hasn’t read the message yet. Limping through the venue with one flappy boot like I’m starring in a tragic medieval drama, I finally reach the parking garage — only to realize my sock is now soaked from water seeping through.
JUST as I’m about to make my great escape, he arrives. Happy. Excited. Enthusiastic. Meanwhile, I’m standing there looking like a wet Victorian orphan.
I try to explain. Badly. He insists we go buy new shoes. I’m dying inside because — minor issue — my personal bank card was recently canceled, and all my money is chilling in a temporary savings pocket. I have to manually transfer it to my business account — my only working card — before I can buy anything.
Cue me sitting there silently screaming, trying to figure out how to sneakily make a mobile banking transfer under the table without looking like I’m applying for a mortgage.
To make it even worse: He initially suggests we go to the most expensive boutique mall in town. I’m sitting there thinking, “Dear God please let my data connection work. Please don’t let my card decline. Please don’t let me look broke. I swear I have money, I’m just trapped in banking hell.”
At the shoe store, just as I’m awkwardly fumbling for my business card — STILL planning to explain how totally normal it is for a girl to pay with a business account on a date — he just grabs the shoes and buys them for me.
No hesitation. Just kindness. Meanwhile, I’m trying to discreetly shove the corpse of my mom’s boots into a plastic bag in his luxury car, pretending none of this ever happened.
Despite all of this? The date went really well. He kissed me. He wants to see me again. I, however, still wake up at night haunted by the sound of my sole detaching like a medieval catapult mid-venue.
Moral of the story: Check your mom’s boots. Transfer your money ahead of time. And maybe… just maybe… accept that if someone likes you, they’re probably not judging your soggy sock.
TL;DR: My boot fell apart, my banking situation was a mess, I almost staged a stealth escape, but somehow ended up with new shoes, a kiss, and a second date.