My Gut-Wrenching Date With a Gold-Digging Guy

heart filled with cashWhat you are about to read are horrifying tales of love gone wrong just in time for Valentine's Day. Welcome to Dating Horror Story Week on The Stir ...

I've always been openminded when it comes to dating, probably to a fault. What I mean is I usually give a guy the benefit of the doubt or assume he's normal/polite/an upstanding person until he proves otherwise. I've lived and dated in a handful of mega-metropolises, from Chicago to Boston to London to NYC, but wow oh wow, of all of them did L.A. do a number on my trusting, Midwestern nice girl approach! Dating in the land of all that's phony is the WORST!

I had more than my share of run-ins with rotten jerks while living in Hollywood, but one situation in particular scarred me for life ...


*Some names have been changed to protect the identities of the main characters in this story.

I met Sam* online, like I did the majority of the guys I went out with while living in the big, huge, often aloof City of Angels (ha!). His was one of the faces that came up in my searches all the time, but I just wasn't feeling like making the first move for some reason. I just wasn't feeling it. (Should have made a note to self: Trust your instincts better next time.) But he must have seen me and messaged a few times. After a few decent conversations in which we realized we had a handful of things in common -- parents in Florida, a love of NYC where he was from, etc. -- he asked me out, and me being Little Ms. Openminded, I thought, "Eh, what do I have to lose?" (Hmm. Let's try ... my sanity?)

Pretty sure he suggested I pick the place, and there was a nice Greek restaurant I had been wanting to try, so we ended up there. Throughout dinner, Sam bragged about being a producer (of what I'm not quite sure) and offered up materialistic blather about fancy cars and summers in the Hamptons. I was trying to give him a fair chance, but at the time, I was a new college grad, working as an intern at the time, making minimum wage, and aiming for financial independence from my parents. I had little to no patience for bratty men in their mid-20s still living off of Mommy and Daddy. In the back of my head, I remember thinking, "What a spoiled prince."

While he talked, I chugged glass after glass of ice water, hoping and praying for the date to get done sooner rather than later. Finaaalllyyy the check came. Yet, he kept talking ... Five minutes later, still talking, check still sitting there. I made a move to get my wallet, but he kept talking -- and not about the bill. 15 minutes later, the plain black leather folder was glaring at both of us. Sam seemed impervious, I was totally confused.

I excused myself to the ladies' room, and thought to myself, It was a first date, right? He had asked me out, right? But he doesn't seem to want to pay (even though he keeps bragging about how rich he is, but whatever). So should I be the one to offer to pay? Ugh. I will if it means I can get out of here faster!

So I get back to the table and he's still pretending like the check isn't sitting there, and I can't take it anymore, so I figure out a way to transition to talking about the check. I say I'll pay. He says, "Okay." But then, the waiter comes by and says he can't accept my debit card. They only took cash, but I didn't have cash. What the hell! So I look at Sam, and he says, "I guess I'll wait while you go get cash." No joke.

As luck would have it, there wasn't an ATM in walking distance (no one walks in L.A. anyway), so I had to drive to one, and come back with cash in hand for the bill. INSANE! (Did someone cast me on Curb Your Enthusiasm without my knowing???)

And if you thought that was the end of the story, oh, hahaha, no, I only wish. After that, the guy still thought I wanted to see him again, and when I tried to be honest and spelled it out for him that no, sorry, I did not, he threw a wild temper tantrum hissy fit. Nasty email and all. Ooof.

And this was the birth of my realization that first dates should almost never be dinner dates. Drinks? Yes. Happy hour? Perfect. But sitting down for a fancy meal with a guy you don't know from Adam ... As it turns out, often more terrifying than you would think. *shudder* 

More Dating Horror Stories:

My Date With the Violent Blue-Eyed Boy

My Valentine's Brunch Date With a Potential 'Serial Killer'

My Date With a Sexual Harasser Who Lived in His Mom's Basement

Has the bill ever become a huge issue on a horrifying date?


Image via Joe Shlabotnik/Flickr

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