The Worst Date of My Life

I’ve been thinking about writing this post for a while. It’s a horrifying story and I’ve been sitting on it for some time. So when fellow blogger IntrigueMe announced her Worst Dating Story Contest, I thought I’d spring into action.

This humdinger of bad dates took place about three years ago. It was one of my first forays into the mad, sad world of online dating, and I had a lot to learn. Of course, I didn’t know this at the time.

My date had looked cute in his pictures, which were all professionally shot. He was 35, CEO of his own company and from Greece. I had become an alcoholic on the Greek island of Ios once after college, so I thought we’d have a lot to talk about.

Oedipus and I exchanged only a couple short e-mails then spoke for about three minutes on the phone to set up the date. At the time, I thought this brief amount of pre-date contact a good idea. I’ve known people who had long, drawn out e-mail and telephone courtships only to meet the guy and discover it was puke at first sight.

Oedipus unilaterally decided we would go see “Live Free or Die Hard,” starring the aging Bruce Willis. Now, the thought of seeing this movie made me want to retch free and vomit hard, but I decided to be a team player and go along with it.

Bad Start

We chose to meet in front of a restaurant in the Westwood Village, home to UCLA and one of the most congested areas in Los Angeles. Finding parking there is about as likely as finding a real pair of boobs in Beverly Hills.

I was driving around in traffic, looking for somewhere to park when he called my cell phone. He said he was parked right outside the restaurant and that I could take his spot. He was familiar with the area and would park somewhere else. Nice, I thought.

He saw me drive by and tried to direct me toward him, telling me to make a U-turn. However, the intersection looked like a free-for-all and a U-turn was illegal. I turned right, intending to flip around somewhere safer, then make a left back onto the street where he was.

“What are you doing?!” he yelled. “I told you to make a U-turn!”

I told him my plan and he said, “Jesus.” I made it back onto the street and searched for his face in front of the restaurant.

“I’m right here! Stop, I’m right in front of you!” he said.


“In the silver Porsche.”

He was sitting in the car? Mmkay. He pulled out of the spot and allowed me to parallel park.

Oedipus sat there in his tricked-out tiny penis car, expecting me to get in. I wasn’t thrilled about climbing into a stranger’s vehicle, but I took a chance and hoped he wasn’t a serial rapist.

I got in and the first thing he said was, “Meh, meh, meh, you drive like my grandma.” Wow. I love it when a guy opens with an insult.

“Nice to meet you, too!” I said.

He looked me up and down and told me I was really sexy. He said I looked even better in person, and then asked me if he looked like his pictures.

I stared at him. He was definitely not as cute sitting there in front of me and appeared considerably heavier.

“Well… More or less,” I lied. Thirty pounds more; much less attractive.

He immediately began to brag about his car, even though I hadn’t asked about it.

“I had this baby custom made — there’s no other Porsche like this. The spoiler is one of a kind,” he boasted. “But I don’t like to drive it. It attracts the wrong type of woman.”

Really? Yet you drove it tonight, didn’t you? In fact, I’m guessing you arrived an hour early to get that choice parking spot during prime time and made sure I saw you sitting in it.

I asked what time the movie started and he said he didn’t know. Idiot.

From Bad to Worse

We drove to the theater and discovered the next showing was at 10:05 p.m. It was only 8 o’clock and I sure as shit wasn’t going to make idle chitchat with this nimrod for two more hours. I told him 10 p.m. was too late since it was a work night. He said fine, we’d go to the Apple store in Santa Monica so he could check out the new iPhone, which was being released the next day.

Santa Monica was about seven miles away and I had a very bad feeling about this. But before I could speak up, he flipped a bitch in the middle of Wilshire Boulevard and peeled out. I looked back longingly in the direction of my car.

I decided to make the most of it and initiate some light conversation by asking what brought him to the U.S.

“The money, baby, the money!” he said. “The money is here, baby!”

“But money isn’t everything, you know,” I said.

“Well… I guess. But it can buy a lot of nice things, baby,” he said. I am fairly sure he thought my name was Baby, because it’s how he addressed me throughout the date.

Oedipus went on to talk about his business dealings and blah de blah. Then he said he didn’t really want the iPhone because he already had the best phone on the market, custom ordered from Sweden. He showed it to me. It looked like a phone.

From Worse to Just Fucking Kill Me, Already

After we parked, we started walking down the 3rd Street Promenade and he tried to grab my hand. I grabbed my purse strap. He made a little sour puss face and I pretended not to notice.

When we got to the Apple store, he grilled the skinny white boy who worked there about why their OS was so shitty. The boy didn’t know how to answer, so Oedipus just walked away, again reaching for my hand. I didn’t extend it, which really pissed him off.

“What is wrong with you? Why do you have to be so cold?” he demanded.

Because you’re a self-important, money-grubbing, obnoxious piece of Eurotrash, asswipe.

“Listen,” I said. “Just because I don’t want to hold your hand doesn’t make me cold. I don’t even know you.”

“Maybe I should just take you back to your car.”

“That sounds like a fantastic idea.”

We began walking back when he said, “I don’t need this crap. I want someone feminine who can let a man be a man, not some psycho.”

I’m the psycho?” I said. “You know what? I’ll just find my own way home.”

“Fine,” he said, and left.

Shit. I was stranded in Santa Monica. Couldn’t I have just kept my friggin’ mouth shut until I got to my car?

I looked at my phone. It displayed one remaining bar. I called my gay bf, praying he would answer. Voice mail.

I called a couple other people and got their voice mails as well. My phone was about to run out of juice and I’d be up shit creek. Fuuuuuuuuck.

I considered a taxi but there were none around. Plus, it would cost me about $30 and I had no cash. I wandered around 3rd Street by my lonesome, trying to figure out what to do while sneering at happy couples passing by.

A few minutes later, the phone rang. It was my gay bf. He told me to stay put and he’d be right down. Saved by my gay!

The worst date of my life had finally ended, lasting all of 50 minutes. On the bright side, I learned a lot from this ghastly rendezvous:

  1. Be wary of professional photos.
  2. Talk to the guy on the phone for a bit before the date to make sure he’s not psychotic.
  3. Don’t get into a stranger’s car, ever.
  4. Charge phone before departing.

And most importantly — always, always have your gay bf on standby to rescue you. He may not be Prince Charming, but he is still 1,000 times more desirable than Prince Shit-for-Brains.


This will be my last post for the year, kids — taking some time off for the holidays. Have a nice Christmas/Kwanzaa/Hanukkah or whatever you celebrate and a naughty new year!

Categories: True Story

Tagged as: , ,

32 replies

  1. I avoid rich guys like the plague– ESPECIALLY if all they do is boast about their living situations and their toys. It just makes me realize that all they’re going to talk about is themselves. The rich ones who are humble about it are great!

    • Agree. And if they talk about it all the time they obviously must think they need that stuff in order to get a girl. What does that say about their personality?

      Yeah, rich guys don’t do it for me simply because they’re rich. They need to be hot, too.


  2. Oh wow… that is a bad date. What a douche! Gotta love the gay buddies who always have your back though! A gay bf is far better than a straight one. 😉

  3. Hi-larious: “Oedipus sat there in his tricked-out tiny penis car”

    And his phone . . . looked like a phone.

    I can’t believe he called you cold.


    This is one shittyass shitty ass date.

  4. I feel your pain…except I talked to the guy for a month on the phone after meeting him out…ummm yeah so he showed up in a car with no air. 100 degrees here..the car’s started on fire…then he proceeded to tell me that he only had one testical…yeah TMI even if I’m a nurse

    • Hahahaha, one ball? How do you even work that into conversation? Geez, dude, leave a little something to the imagination, will ya? I’m reminded of this childhood song:

    • Sorry KAP – I can’t believe my work made me delete my blog. I didn’t know we were still living in communist Russia. Jeez. I’ll be back. I’ll find a stealthy way.

      • @KAP Aw, family stuff is depressing. Care to share a Prozac/Zoloft/Phenobarbital cocktail, my love?

        @VGB What-what-whaaaaat? Your work made you delete your beautiful blog? Do you work for Neo-Nazis, or worse, Texans? We must revolt. Let’s throw flaming shitbags on their front doors. Please keep us posted, we need you!

    • Yeah, he was a loser. But it was my own fault – I shouldn’t have gotten in that car. And then I just couldn’t bear to be with him for even another 10 minutes in the car ride back. Live and learn.

    • Hahaha, I know what “comprehensive” means – l o n g. Yeah, I know. I usually edit posts down a lot more. But on this one I just had to include every pathological detail of this wacko. Thanks for sticking with it, girl.

  5. Wow and I thought my first dates were bad. I once had a girl meet me in a bar and wanted me to bum smokes off other people because she was saving her money to buy beer later.

    Good on you for taking out the eurotrash.

    A very Merry Ho HO HO OHHHHHH to you as well!!

    Santa Bob

    • Well, well, well… at least you had a girl who was smart with her cash. She sounds really classy. Wonder what would happen if we set up your bad date with my bad date. That would be fuuuuuun to watch!

  6. I had almost the same date…. TOO FUNNY…. and he called me bebe about 782 times I do believe!!! OMG… sista!

  7. ALWAYS avoid those that need to show off. Especially that early on in the date.

    He tried to hold your hand? Are you serious? I’d say he was hoping to use you like another sexy accessory. Like his car.

    I’d also say always avoid dudes who want to take you to horrible movies on your first date. Then I remember my ex took me to see “Snakes on a Plane” for our first date. And then didn’t have enough money to buy my ticket. Sure – some signs of what was to come, but we dated for six months and he was, and still is, a good guy.

    Not like this douch canoe. I’m sorry you’ll never get those 50 minutes back.

    • You’re right, the poor movie choice should’ve been a tip off. I’m sure during the action sequences he would’ve said, “My car flies faster than that.” Luckily your guy wasn’t a douche canoe – love that moniker by the way. Will have to work that into a conversation somehow. 😉

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