Why I Tried This
Look I’ll be straight with y’all – last weekend my buddy Mike bet me 50 bucks I couldn’t find a street walker near downtown in under two hours. Honestly? I’d never tried anything like this before but cash is cash so I grabbed my phone and wallet.
The Step-by-Step Process
First I just drove around sketchy neighborhoods with my windows down near 8th Street cause that’s where people say these things happen right? Total waste of gas. Only saw normal people walking dogs and some homeless guy yelling at a mailbox.
Next I tried hotel bars because I’d seen that in movies. Sat at the Marriott bar drinking overpriced beer for like 30 minutes. Got awkward real quick when a business lady started chatting about spreadsheets. Ducked out when she asked if I had LinkedIn.
Then I remembered that Craigslist section people whisper about. Searched “women for company” postings at 9PM and got excited when I saw one saying “new in town need help”. Messaged the number and it was actually someone’s grandma selling handmade quilts. Swear my face was burning red hearing her describe stitch patterns.
Finally around 10:30PM I just drove super slow past truck stops on Highway 6. Saw a lady in fishnets near a rig and pulled over. Heart was pounding like a drum solo when she approached my window asking if I wanted company. Told her it was just for a bet and she laughed saying that’s the weirdest thing she heard all week.
How It Actually Went Down
- Made eye contact: Kept driving loops til I saw that bright pink wig
- Parked crooked: Hands were shaking bad when I rolled the window down
- Chatted briefly: Asked how her night was going outta nervous habit
- Showed the cash: Held up Mike’s 50 like an idiot explaining the bet
- Got proof: She flipped me off while laughing and let me take a blurry selfie
Why I’m Sharing This
Lost the bet technically since it took 2 hours 15 minutes but whatever. Mike refused to pay anyway saying “finding” meant actually hiring someone. Whole experience felt scummy and stupid – walking back to my car I saw cops pulling over another guy doing the same thing. Don’t be like me wasting a Friday night playing Sherlock Holmes for pocket change.
