What’s the Worst Date You’ve Ever Been On?
Happy Valentines Day!
Let’s do something different. Today, we’re going to have a little fun. We’ve earned it, right? On this special occasion, we’re going to try and recall the absolute worst dates of our lives.
I considered asking my faithful readers to post stories about their best dates. It is Valentines Day, after all. Thing is, the very best dates either lead to weddings, or if they’re truly amazing — maybe really wild and happened at the end of the night which might best remain unspoken.
So instead, let’s find some common ground and focus on the worst dates we’ve ever had. Everyone’s been on a bad date, so we should all be able to play along.
I got married at age 29. That means I spent about ten years playing the dating game. Like most everyone, I went out on some good dates and some bad dates. Most of them, I don’t remember much.
But I sure remember a Saturday night that happened sometime in 1987.
My worst date happened when I was around 25. I met a girl somewhere, I forgot where exactly. Attracted to the girl, I gave her my phone number and asked to call if she wanted to go out sometime. To my surprise, she called just a few days later. We talked for a few minutes and agreed that I’d pick her up Saturday night and take her out to dinner. We may even have discussed going to a movie, as well. I think Platoon had just been released.
Saturday comes around and I’m supposed to pick her up promptly at 6. I get into my car and the piece of shit won’t start. The bastard battery was dead. Frantic, I tried getting a jump start but didn’t have any jumper cables. Utterly desperate for transport and the clock ticking fast to 6, I called up my friend, Iranian Mike, a gambling buddy of mine who lived about a mile away. I begged him to borrow his car for the night. He said okay. Iranian Mike even agreed to drive his car over and let me have it so I wouldn’t be late for my date. Man, what a pal. I think he might have owed me some money, so this made us even.
When Iranian Mike pulled into my apartment complex, I couldn’t believe my eyes. He drove a dark blue Oldsmobile. A Cutlass. It was filthy. There was dog hair all over the seats. He had a small Shitzhu and the dog rode in the car all the time. It was summer in Texas, so the dog shedded like crazy. Worse, Iranian Mike’s car had a flat tire a few days earlier and was riding on one of those small donut-shaped emergency tires that was only intended as a temporary replacement to make it to a service station. Iranian Mike tossed me the keys and told me to bring it back in one piece.
I can’t even fathom what must have gone through the girl’s head when I pulled in to pick her up, driving that dark blue Oldsmobile Cutlass of a shitbox with dog hair all over the seats and a tiny tire that made the car pull off to one side.
Hey, the night was still young. Then, things went downhill from there.
I feel bad not remembering the girl’s name, right now. So, I have to call her “the girl.” If you’re reading — sorry girl. She listened to my sob story about the car not starting and having to borrow a friend’s car at the last second. I think she kinda’ appreciated the effort. She even believed me for a second.
We pulled into one of the best Italian restaurants in North Dallas, Lombardi’s on Lower Greenville. This was my go-to place. Great food. Live jazz on weekends. I’d even made a dinner reservation in advance. What a gentleman. A player.
The next 90 minutes were excruciating. Ever been in a confined space, trapped in a sit-down situation, and within 5 minutes you know it’s already a disaster? How about this: Ever been crucified? That was this date.
We had absolutely nothing in common. I mean, nothing. Everything she liked and enjoyed, I detested. Every topic I brought up, she took no interest in. But, she had a great ass. Man, I couldn’t get the check fast enough.
We both went through the motions. We gave it the old college try. I remember as we were looking across at each other one of those cozy two-top tables meant for couples truly in love, recalling that many odd relationships start off sailing on rough seas before calmer waters. Indeed, many love affairs do begin when the two people can’t stand each other. But this wasn’t that. She didn’t dislike me. And I didn’t dislike her. The date pretty much just ended up like walking up to a stranger on a bus and saying, “hey, let’s hang out together for a couple of hours.” What would one expect? Rolling the dice like that, what are the odds it’s going to work out and you’re going to keep hitting your point? Dating is/was just a numbers game. Keep tossing and eventually, you hit the 7. But along the way, there’s a few boxcars and snake-eyes. This date wasn’t like crapping out. It was like misfiring with two dice bounding off the table. A miscue. A bad roll.
The waiter brought over the check and by this time there was no chance in hell we were going to that movie. Even if I really wanted to see Platoon. All I wanted to do was pack her into the passenger seat with all the grey dog hair and wheel her back to her street, prop open the side door, and slow down enough to let her get a running start when the stilettos hit the asphalt.
But first I had to pay the bill.
Dallas — we have a problem. When I reached for the check that’s when I suddenly realized this night was about to become so far beyond a humiliation that I think I just lost it right then and there and began to burst out laughing.
A few hours earlier while trying to find a jump start for the car, I’d switched jackets. That meant I’d left my billfold in the other coat pocket. The billfold had all my money and credit cards. So, I was sitting at a dinner table on a Saturday night penniless. Flat fucking broke.
I think I was laughing by this time. Crying, maybe. I don’t remember. The girl must have thought I was insane. If there was a bridge nearby, I probably would have jumped off it.
“Umm, you’re not going to believe this, but umm…..”
Whatever syllables followed next from my trembling salty lips aren’t important, nor are they remembered exactly word for word, some three decades later. However, I do remember this. My date actually gasped for air. Then, she just stared. Sort of like a death stare. Then, she calmly reached into her purse, tossed some money on the tabletop, and confessed she needed to go to the ladies room immediately. Yeah, I totally got that. I could surely understand. I’m stoked with empathy. The girl needed to catch her breath. Take a little break. I’m sure our date had been quite overwhelming.
Well, I sat there by myself with my hands over my face in silence for the next ten minutes. The agony seemed a lot longer than that. It sure seemed like a long time for her to be using the restroom. So, I left her money on the table and approached to the hostess stand. I was still clueless.
“Hey, did you see a brunette lady in a polka-dot dress up here? She’s my date. I can’t find her.”
“Yeah, she jumped in a taxi and left five minutes ago.”
Can you believe that? I didn’t even get a kiss.
Well, at least I got a free dinner out of the worst date of my life.
Note: ‘Tis the season of love. Now it’s your turn. Please join our fun at Facebook where readers can post their WORST DATE EVER stories in the “comments” section. My last poll question got about 230 replies. This one should be a blast. CLICK THE LINK BELOW: