Bad dates make great stories, especially when the date completely crashes and burns. Like this one! We teamed up with The Single Society to share all of the dumpster fire dating disasters women face in this bizarre era that is digital dating. If you have a trainwreck dating story like this one, share that sh*t here!
I showed up to a cozy Williamsburg cafe for what was going to be the most awful Tinder date of my life when I reluctantly agreed to meet Garett, a self-proclaimed 'serial' entrepreneur who I knew was probably going to be a total douche from the start, but it was Friday night, and (sadly) I had nothing else on the agenda.
Pathetic. I know.
I was the first at the scene, so I ordered a glass of Petite Sirah and surrendered my American Express to the bartender to open up a tab. Garett arrived, and immediately expressed his remorse for his unpunctuality.
'So sorry I was late, I had to fly out to Pennsylvania because one of my rental properties out there had a flood, and I had to do some damage control. I jumped on my plane right after and got here as quickly as I could.'
Your plane? You have a plane?' I asked.
Asking about his plane was a huge mistake that I immediately regretted.
Garrett pompously whipped out his cell phone and began showing me his beloved propeller plane as if it was a newborn baby girl. This went on for roughly 25 minutes.
At one point he offered to fly me to Connecticut the following weekend to go wine tasting.
Garrett then proceeded to tell me about the various businesses he had started and his elaborate plan to retire at age 40. He ordered several double shots of tequila on the rocks as I finished my first glass of wine.
"Oh, I guess we are neighbors then! My brother and I live in the building 2 blocks over by the same management company!"
After discussing some favorite spots on our street for a few minutes, Garrett revealed the details of his rather peculiar living situation.
"It's a bit tight right now, my older brother and I share the bedroom, and my youngest brother just sleeps out in the living room. Really trying to save some money."
"…but you own a plane?' I reiterated. 'I would have to imagine owning one of those is extremely expensive."
"Yeah, the plane is my baby. I would rather share 600 square feet with my brothers than give up my plane."
By his third double tequila and only my second glass of wine, his speech was slurring, and I determined it was time to call it a night.
The bartender came over and asked if we would like to put our drinks on the card he was given to which Garett eagerly replied, 'Yeah that works!'
I got my bill, and the total came to $127.62.
'Jesus Christ, what were you drinking? Crystal?'
'Oh, yeah. Sorry, I only drink top-shelf. Didn't realize I drank so much though! How about I get you next time?'
'No, Garrett. I had 2 glasses of wine that were $12 each. How about you just Venmo me $100?' I suggested.
He proceeded to offer up the excuse that he didn't have Venmo, so I suggested we run to the ATM next door.
'I don't keep that kind of money in my account.'
'Garett, you don't have $100 in your account? You just spent an hour telling me about the plane you own and how you are retiring in 5 years.'
At this point, it was a lost cause. I kissed my $127 goodbye and kicked Garett to the curb.
He was never to be heard from again.
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