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.