Worst Date Challenge

Hillary recently said that there is a meme going around about worst dates ever. Long ago, back when I was single and this site was called Martinis For One, I actually wrote about my worst date. And because I'm busy entertaining friends this week, I decided to dust it off and replay it. This post comes with a challenge, however. I ask that readers write about THEIR worst date in return. Are you up for the challenge?

It started off innocently enough--four women, two bottles of wine, and one fine-looking Italian waiter, who kept touching my back as he spoke to our group.

"Can I get you anything else?" he asked with a glean in his eye.

I tried not to read too much into his behavior during dinner. But when I went to pay the bill, Pete the waiter asked for my number. And because of an uncharacteristic, if not slightly insane, impulse, I decided to fork it over. Why not? More often than not, the call never came anyway. But two days later, Pete did call. We agreed to meet for drinks at a swanky little downtown lounge.

Maybe it had been that second bottle of wine at dinner the first time we met, but Pete looked somewhat different on this occasion when he arrived outside of the lounge. Dressed in a baby blue jacket, heavy cologne, and a little too much bling bling bling, he met me at the door.

"Diane," he started in his heavy Italian accent, "I want to thank you for agreeing to meet today."

How sweet! The thoughts of appreciation almost made me forgive him for wearing the baby blue jacket. He opened the door, held the chair, and ordered my drink --a take charge sort of guy. I liked it. We sat in silence until our libations arrived, then Pete began to open up.

"Is the drink to your liking?" he asked. "If not, I will send it back."

"Pete, the drink is fine." I said.

"Are you sure? Would you like something else? A martini, perhaps?" he asked again.

"Everything is fine, really." I then decided to change the conversation in an effort to put my date's mind at ease.

"So, tell me a little bit about yourself. You seem like such a nice man."

Pete winced. I wasn't sure what to make of his body language until he opened his mouth,

"Diane, I'm going to be honest with you because you are a nice girl. I don't want to lie to you," he said.

"I am not a nice man."

"Uh oh." I thought, but said nothing.

"I've lived a very hard life. Both my parents died suddenly in Italy, and at fourteen years old I went to live with my uncle in New York. We didn't get along. By sixteen, I was out on my own."

I felt sorry that Pete had endured such a rough patch. Maybe being out on his own at such a tender age had forced Pete to grow up a little too soon. What was so bad about that? It was obvious this topic bothered Pete, so I attempted to lighten the conversation by asking about his work as a waiter. Again, Pete winced.

"Honestly, Diane, I am not a waiter. My friend, Johnny, owns the restaurant and he thinks there is a problem with the some staff. I did a job for Johnny one time in Miami. So he called me in to find out what's what. "

"So, you're an undercover waiter?" I probed.

"Well, yeah. I go in when I feel like it--a few hours here and there. It's just until we take care of the situation," he replied.

All the time he talked, I noticed that Pete kept looking around the restaurant. I tried to follow his glances to see what was taking so much of Pete's attention away from me. He noticed my confusion.

"When you grow up the way I did, you learn to watch your back," he said by way of an explanation.

"Even here in small town USA?" I asked.

"Everywhere and all the time," he said with a steely look that stopped me cold. Then, his tone changed. "Now, we go for dinner."

Dinner?!? Before I could get the words out to end the evening, Pete had whipped out his cell phone to make arrangements.

"Lou, it's Pete. I'm bringing a young lady over for dinner. Have my table waiting for me," he ordered.

There was no disagreeing with Pete; saying no was not an option. Before I knew it I was in Pete's red sports car (that could not have been purchased on a waiter's salary), speeding down the interstate to a neighboring town 20 minutes away. "Great going, Diane," I thought to myself. "Here you are alone with a stranger. No one knows where you are, who you are with, or how to find you."

Again, I tried to lighten the air and pass time by conversing with Pete. When he winced again, I knew this was not going to be a mood-enhancing chat.

"I hope you like this restaurant. Back in the city, I did a job for Lou, the owner. I took care of Lou, Lou takes care of me. Nobody wants to get on Pete's bad side."

Note to self: Don't get on Pete's bad side. It also hadn't escaped my notice that we were now referring to Pete in the third person. Pete was referring to Pete in the third person. I was referring to Pete in the third person.

"So," I said, "Pete has lived in Miami and New York." Which was his favorite place?"

"New York (wince)," he answered. "But I can never go back there." I opened an establishment (wince) at one time. And well, you know, with surprise visits and all, it was shut down. No...I can't go back (wince)."

By this time, we arrived at a posh, but dark, cramped restaurant that reminded me of something out of The Godfather. As soon as Pete walked through the door, the owner, Lou, made a bee line for him. Our table was ready, garnished with a $100 bottle of champagne. Fortunately for us both, I was ready for a drink.

"Do you like this champagne? If not I'll send it back? Would you like a martini instead?" Pete offered.

"Oh, oh, oh" I thought. "I could really use a shot of tequila right now."

With every question I posed and every honest answer Pete offered, his winces became more pronounced. From the vantage points of casual observers at adjacent tables I am sure it looked as if Pete was in some serious pain or suffering from Turret's Syndrome. He didn't want to reveal himself to me, but felt compelled to tell me the truth of his life because I was "a nice girl."

I learned through the course of our night that my fine, Italian, undercover waiter with all of his bling bling bling and baby blue jacket, had serious gambling problems, which had caused the end of relationships and financial woes. But despite all the setbacks his addictions had caused, Pete liked living the hard, fast life and taking risks. And although he really wanted to meet a nice girl and settle down, Pete also knew, quite well, that nice girls wouldn't be attracted to his lifestyle.

Through out our entire conversation, I smiled and made pleasantries. But at the end of the evening when Pete asked for a second date, I got the chance to share a truth of my own.

"Pete, I appreciate your candor this evening, and I want to be honest in return. I lead a very simple, uncomplicated life. I am afraid your lifestyle would be too stressful for me."

"Pete understands," he said with a smile. "and will pick you up for a movie tomorrow at 7pm."

And all I could do was wince.


Andrea said...

Ok, I'd be running as well, if it was possible. So did you have to change your name??

Good post :) And I like the look, minimal is good.

Andrea said...

Ok, I posted a worst date night memory, hope you like :)

Princess Extraordinaire said...

Oh you poor thing - Pete is...ummm...eccentric???I will post a worst date nightmare next post as I just posted something else this very minute...

headbang8 said...

Can't participate, Diane. We gay men don't date.

Gay men say hello with their genitals, as the saying goes. (The saying usually goes a bit cruder than that, actually.)

Oh, I cringe when I read about dates of any kind, even "good" ones.

Love, HB8

running42k said...

Great story. How did you ever break up with Peter?

Diane Mandy said...

andrea - yey! I knew I could count on you.

princess - Thanks! I'll look forward to it!

headbang - Gay men don't date...really? I must admit I am disappointed. I would have loved to read your worst date story.

running 42k - Pete never knew where I lived and I had an unlisted number. So, I did the scummy thing and never showed up for date #2. Is that terrible? DO you think less of me?

Chica said...

Pete is disconcerting, good call on the second date ditch! x

patches said...

Self-preservation should not be confused with standing up a guy on the second date.

Cheryl said...

OH man, the third-person referencing is like the icing on a very bad cake. Like a cow patty.

kenju said...

Well, obviously he was a refugee from the Mafia (or wanted you to think he was). I wonder what happened after that? LOL

AmyD said...

Um...does Diane know that Diane was probably on a date with a hitman?!?! ;o) How did you get past this one? Hopefully it wasn't too hard to shake him off?

WOW. Thanks for sharing! I have no bad date stories to share that could even TOUCH this one. All I've got is the guy who was really short (and had a Napoleon complex) and practically had to be hoisted into his big-boy truck. *wince*

LZ Blogger said...

Diane ~ I hate to even admit this one (and you’ll never see this on my blog) but my worst date never actually happened… WHAT? How can that be? Well it goes like this…
I had a date for my girlfriend for her Senior Prom on a Saturday night. A buddy of mine convinced me that I needed to drive with him down from our homes in Orange County, California to TJ (Tijuana Baja CA., Mexico) so we could party on Friday night down there. The night before the Prom. Well I thought; “That sounds like fun!” I was only 18 at the time and when you went down to Mexico they didn’t really care how old you were to drink, let alone how much you drank, or even how long you drank. The fact that you were able to pay for it was all that mattered. You may have figured out where this story is going. Yes! We drank all night long into the next day. We passed out in his car at about 9:00 A.M. on Saturday morning (while still) in Mexico. By the time I woke up, I had less than an hour to get 100 miles to not only get home, but to also get dressed in my tux and to be at her house to pick her up. My buddy was still too drunk to drive (or even stay awake), so I made him get in the back seat of his car as I drove us (way too fast) trying to get us back to Orange County. Well… somewhere between National City and San Diego (around Chula Vista I think), I was arrested by the C.H.P. for reckless driving, excessive speed, following too close, defective foot brakes and a couple of other things that I can’t even remember now, but fortunately I was NOT cited for DUI because by then, I had sobered up enough to pass the simple “white-line walking” sobriety test. But I did have to spend the night in jail, which did not bid well with my girl. But my buddy did wake up and bailed me out on Sunday morning. My girl did however show up at my door the next day (Sunday evening) and told me “it was OK” but that I had to make it up to her (and her parents) by taking her out to for a formal dinner with photos of the event to satisfy her parents. When I agreed and showed up at her house to pick her up, everything seemed fine, but when I brought her home, her dad (who was an over-the-road trucker) came out on the front porch and began hitting and kicking the crap out of me. I never lifted a hand toward him (except to protect my face). I actually even understood his anger and just let him keep throwing blows to my face and body. His daughter was yelling at her dad to quit beating me and was even trying to stop him. He finally stopped punching me and then he told me to leave his house and to NEVER come back there again. He also said if I ever came back to get his daughter, he would meet me at the door with a shot gun. She however came over the next day to my house and apologized for her dad’s actions. Partially because of what her dad had done to me, as soon as she turned 18, she moved out and got her own place. Several weeks later the judge beat me up too. But that’s another “Worst Date”, that I’d rather not go into! She and I did date for a while after all of this had passed, but then I moved on because I could not see how this would EVER be right with her family again. And frankly, I though he might show up on my porch with his shotgun some night. I don’t know if she ever reconciled with her dad. The last thing I heard, she had moved to Texas and got married to a guy she met there a couple of years later.
~ jb///

Me said...

That's HILARIOUS...that ending..oh my. How did you get out of the movie??? LOL

Diane Mandy said...

LZ- Your story definitely beats mine by a mile! But it sounds like you made the right choice to to end up with her and her family! That father sounds scary!

Ron said...

OMG, Diane...that was HYSTERICAL!!!

The way you wrote this...I felt like I was actually on the date with you guys, sitting in the table across from you, listening and peeking.

You really paint a wonderful picture with your words!!

Oh...and hey, your blog changes look absolutely FABULOUS!!! This is the first time I've seen it!!
I LOVE the header. The whole template looks WOW!

Good going, Diane!

I'll have to think about this and maybe do a post on my blog about my worst date. I really don't date much, so I'll have to put on my thinking cap!

But this definitely would make a GREAT post!

Thanks for sharing this!

That was great!

evercurious said...

I love this post! Sorry you had to endure it though. I might add one to my blog about my worst date.

karey m. said...

oh, i loved this! too funny. had to kirtsy!


and your new look? i love love love it. so clean! xoxo.

A Touch of Dutch said...

Diane, I don't know if I can top yours! And you share it so well! I've had some real dandies myself.. But I wonder how I can combine it into my blog & make it fit with the whole theme I have there.. To make a long story short, my worst ones are those who always 'insist' they are gentlemen. Actions always speak louder than words! Also I've learned the worst places to go on a 1st date is where there are little-to-no other people or no taxis available to quickly hail & jump into if the situation goes awry. On dates, my mom taught me to always bring my own emergency money in my purse and especially change for the payphone. Back in those days before cell phones became so common..

Sarah said...

You're kidding!

...Right? :P

Jul said...

Too funny! And LZ, that's a great story.