The single worst date of my life, aka: First, last date; otherwise known as Never reserve a ‘Table for Two’ at Red Lobster

Have you ever been on a really bad date? I have. A few actually. One such example involved a date a neighbor set me up on once with a girl (I’d never met) who was about a foot and a half shorter than me.

Aside from that disaster, there’s one date, in particular, that stands head and shoulders above the rest, and it took place roughly seventeen years ago. For reasons I am about to explain, why this constituted being the worst date of my life was simple: I totally bombed.

If I had to use a Chuck Norris GIF as an example of how bad it was, this is what I felt like during the date as well as after the date:

I’m not a big fan of using the word fart, but the worst date of my life would have been better had I sat across from my date at dinner and farted everytime she spoke. For the record, I didn’t fart even once. But if I had, it would have likely been a better date.

In the history of mankind, I estimate a total of four people know this date ever even happened. After this post goes live, thousands will. Why I’m going public now, all these years later, is beyond me — other than the fact that a little self-deprecation is good for us all, present company included.

What makes a good date?

Before I relay the story of my worst date ever, let’s pause for a moment and consider what often makes a good date.

According to world-renowned dating expert, Dionne Smith, who studied at the University of Sydney and received one upvote on Quora for her response, what makes a good date includes, and I summarize while excluding one of her bullet points (want to jump her bones):

  • Instant attraction
  • Good conversation
  • Shared interests
  • Eye contact

Pretty simple stuff, and the quintessential guide for great advice on the Internet known as Yahoo! Answers is in agreement. King Boo goes even further, offering specific first date tips. Writes King Boo:

Go to, like, a haunted house, then save your girlfriend-to-be from a ghost. Tell your friend to dress up as a ghost or monster or something. Then your girlfriend will think you’re a hero.

It’s like Shaggy and Scooby Doo meets eharmony. I couldn’t have said it better myself.

Now, let’s go into more depth as to what makes for a bad date. Exhibit A:

The worst date of my life

There was this girl I once had a thing for. She had shoulder length brown hair and a deeply southern accent. And according to the grapevine, she had a thing for me, too, and had for some time. One day, after months of being a total chicken shit, I finally got up the nerve to ask her out.

There was a history between us, so she was by no means a total stranger. We had been friends for a few years and all the corresponding boxes, as noted by world-renowned dating expert Dionne Smith from the University of Sydney, had already been checked within that history: attraction, good conversation, shared interests, even eye contact — I knew what color eyes she had and she often remarked how pretty my blue eyes were to her.

Only neither of us had moved past the friendly flirting stage to cement something more. Now, was that time.

In my bid to impress her, I decided to take her out to a nice restaurant. Back where I’m from, restaurants don’t really exist, so my idea of a nice restaurant was always Red Lobster, home of the Cheddar Bay Biscuit. Red Lobster was a bit of a haul from where I lived in Phenix, sixty miles away to be exact, nestled on the corner of Candler’s Mountain Road near River Ridge Mall in Lynchburg, Virginia.

On the drive up, we talked about our mutual love of Red Lobster. I openly pondered whether I would get the Admiral’s Feast. She spoke of the Wood-Grilled Shrimp. An intimate bond began to form as a Prince CD I put together through sheer perseverance of endless hours spent on Napster using dial-up Internet played in the background: “Little Red Corvette,” “Raspberry Beret,” all the hits, and then some.

Because I wanted the night to be perfect, I made reservations the night before.

“Yes, I’d like to make reservations,” I said to the man on the other line at Red Lobster.

“How many in the party?”

“Two,” I replied. “Table for two. Jeff Pillow. That’s P-I-L-L-O-W, like you lay your head on. Spelled the same way.”

“Alright, Mr. Pillow. We have you down for a table for two tomorrow night. We’ll see you then.”

“Thank you,” I said, and then hung up.

When my date and I arrived at Red Lobster the following night there was a long line leading out of the restaurant and numerous others seated in the waiting area with little black buzzers in their hands. Stir crazy children climbed over benches and into their parents’ laps, then to the floor, and back onto the bench. Other rugrats looked at their feet with their pointer fingers up their nostrils searching for a pre-meal appetizer.

“Forty five minute wait,” I heard one woman say to her husband and two children. The husband had this look on his face that said, I’m not sure we can hold them, his eyes gesturing at his kids.

“Alright, we can wait. It may not be that bad. When they say forty five minutes, it’s usually half that,” the husband said.

“Good thing I made reservations,” I told my date.

As I mosied past the lobsters in the tank awaiting their fate of agonizing death from being boiled alive, I approached the host.

“Table for two,” I said. “I made reservations. Jeff Pillow.”

“How many in your party,” the host asked.

“Two,” I said confidently of my preemptive planning.

“I’m sorry sir, but we don’t take reservations for parties of that size.”

Thinking there must be a mistake, I made the host aware of the phone call I had placed the night before.

“I made the reservations last night. I spoke with a man on the phone who marked me down.”

“I’m sorry to tell you, sir, but whoever you spoke with was pulling your leg. We don’t allow reservations for parties that small. I can put you down now that you’re here though.”

Sly son of a bitch, I thought of the miscreant from the night before who had set me up for foolishness on the other end of the phone. Sly son of a bitch.

I looked at my date. My date looked back. She had this look on her face that said, I love Red Lobster and can wait. I had a strong feeling she was still craving the Wood-Grilled Shrimp we had made good conversation of on the ride up and I didn’t want to disappoint her. I wanted the night to be perfect. Even with one strike on me (failed reservations), I still had a couple more swings at the bat.

“I guess so. Two. Jeff Pillow.”

“Two it is, Mr. Pillow,” the host replied, handing me a black buzzer. “Your buzzer will buzz when your table is ready.”

My date and I walked back to the waiting area and sat across from the same young family we had passed just moments before. The son was picking at a hard black spot on the carpet, presumably someone’s tossed chewing gum from years prior.

Small talk ensued between my date and I. She asked me if I had heard the new No Doubt song. I said, “No,” and then segued into a brief history of No Doubt, asking if she knew they originally started as a ska-punk band in the mid 80’s in Orange County, California.

“You should check out Dance Hall Crashers,” I said. “You may like them.”

It was starting to get hot while we waited and I was feeling a bit faint. Part of the reason it was starting to get hot was because I made a decision to wear a sweater on my date — even though it was summer. Due to my punk rock lifestyle, I didn’t have many nice clothes back then. A faded Operation Ivy t-shirt held together with safety pins just wasn’t going to cut it — not on this night.

And so, the weekend prior to my date, I made the trip sixty miles to Lynchburg in search of a bargain at Rugged Wearhouse, and a hell of a bargain I found: sweaters for half off in summer. Jackpot! I wanted the night to be perfect, so I had to look nice. That sweater was mine.

For those of you not aware, Rugged Wearhouse was once a clothing store where you could find brand name clothes at bargain prices. The only issue was that there was something slightly wrong with the garment, perhaps a small hole, bad stitching, and in rare cases, a sleeve that was just a hair longer than the other.

My sweater only had a small hole under the left armpit — totally unnoticeable since I was also wearing a black Dead Kennedys t-shirt. The hole, however, was not small enough to provide what I needed at the time: air conditioning.

I was feeling clammy by this point and my stomach started gurgling — part hunger, part nerves.

Is it hot in here?” I asked my date while doing an impersonation of Nelly, whose hit single had just been released months prior.

“No,” she said.

“I’ll be back in a minute. I’m going to run to the restroom.”

Once in the bathroom I took off my sweater, splashed cold water on my face, dried it off with a brown paper towel, put my sweater back on, and blew my nose. I looked like shit.

“You look like shit,” I said to myself in the mirror.

A very large man walked in and proceeded to blow up the bathroom while I stood in front of the mirror.

I left the bathroom and returned to sit beside my date in the waiting area. The young family was being escorted into the dining area. Their forty five minute wait amounted to all of twenty minutes. The husband had been on the money in predicting half the anticipated wait.

“Somebody had the Lobster Fest,” I said to my unamused date of my bathroom experience. “So, uh, any minute now,” I continued. “Shouldn’t be long.”

Twenty five minutes later, which equated to all of the forty five minutes the host had projected, my buzzer buzzed. By this point, my stomach was gurgling audibly.

“I’m hungry,” I said to my date. Only my hunger pangs didn’t entirely feel like hunger pangs. More like gut spasms.

The host escorted us to a lovely window seat with a scenic view overlooking the historic River Ridge Mall in the near distance, its classic architecture and light khaki exterior the perfect backdrop to the evening.

“Your waiter will be with you shortly.”

Our menus now before us, I flipped to the page with the Admiral’s Feast, which listed off the contents of the classic fish fry platter:

  • Walt’s Favorite Shrimp
  • Bay scallops
  • Clam strips
  • Wild-caught flounder

All fried until perfectly crisp and golden. My gall bladder and young arteries swooned in anticipation of the incoming grease.

“I know what I’ll be having,” I said to my date as she thumbed over to the Wood-Grilled Shrimp.

Shortly after our waitress took our orders, I found myself unable to think of anything to say.

This is a re-enactment of how I looked at the moment.


Except I was wearing a sweater.

There was a painful silence in the air despite me having been friends for years with this beautiful girl who I had shared many good conversations with who all of a sudden was my date.

At one point I actually mentioned the weather in jest, which fell flat on its face.

“Weather sure is nice,” I said. “Kinda hot though.”

“You are wearing a sweater,” she replied.

More time passed in mostly awkward silence. Our food arrives. My date starts chowing down. I feel like I’m going to vomit.

Tiny beads of sweat visibly form on my forehead. My date looks at me with her fork in hand stabbed through her Wood-Grilled Shrimp. Then the tiny beads unleash as if a pipe had burst in my scalp.

“I have to go to the bathroom again,” I said. “Too much unsweetened tea.”

Once in the bathroom, I take off my sweater again, shovel cold water onto my face with my hands, and stare at the mirror.

What the f—k are you doing, I say silently to the colorless face staring back at me. Why did you wear a sweater, you moron?

My stomach is in spasms. I question whether I picked up a stomach bug or whether this perilous activity is a result of nerves and heightened expectation plummeting to its demise. I’ve got this weird cold sweat going on. My eyes are sunken in. I look like death.

In walks a man wearing a short sleeve polo.

Why didn’t you buy a polo at Rugged Wearhouse, I think to myself. It’s summer. They had deals on polos, too. They have deals on everything. And, you bought a f—king sweater in the summer. And not just any old sweater. This thing has weight.

Which was true — this sweater did have weight, and not just the three gallons of sweat it had soaked up over the past hour. It was a corded sweater.

While the man in the polo whistles and I stare at death personified in the mirror, I consider jumping him, slamming his head into the urinal, knocking him unconscious, and swapping out my sweater for his polo. I determine this is a bad idea as he may regain consciousness while I am still seated with my date overlooking the romantic River Ridge Mall lit up in the distance by parking lot lights. Also, my date will wonder where my sweater went and why I am now wearing a polo that’s two sizes too small.

I leave the bathroom and return to my table. My date has all but wiped out her Wood-Grilled Shrimp. My plate is full, my food cold. I start fiddling with Walt’s Favorite Shrimp, not all that hungry.

“I’m not all that hungry,” I said. “I think I’m going to get a to-go box. I wonder if they’ll give me any extra Cheddar Bay biscuits,” I laugh. Swing and a miss.

The remainder of the evening was relatively uneventful. I went to the bathroom and stared into the mirror at least three more times. Then made the executive decision to cut the date short (no putt-putt tonight) because of how I was feeling. Save for a brief conversation about the guitar virtuosity of Prince, you could hear a pin drop on the ride home. Sweater off, cold sweat over, I drive home in my black Dead Kennedys t-shirt.

In route to my date’s house, I pondered whether a good night’s kiss was appropriate considering what had transpired the past four hours. Somehow this thought was still in the back of my mind.

My pondering was in vain. My date made the decision for me. As the car came to a halt in her driveway, the engine of my Toyota Camry LE still idling, she made a break for it and I can almost swear she said MEEEP, MEEEP in progress. This is what she looked like:


“I had a good time,” she said with the speed of her voice as fast as John Moschitta, Jr. of Micro Machines fame as she stood on the front steps leading into her home. “I hope you feel better.”

The next day one of my friends stops by my house and was like, “So, how was it?”

“So, uh, funny not so funny story,” I begin.

I was so humiliated after the fact I didn’t talk to the girl for a solid six months, this despite having been friends with her for years, nor did we ever broach the subject of this horrendous date even once in the aftermath.

I know what you may be thinking, and from your vantage point, you may be correct. There was nothing catastrophic that took place. Your reservations fell through. There was some awkward silence. You spent seventy-five percent of your date in the bathroom staring in the mirror. You contemplated (but didn’t act on) bashing a stranger’s head into the urinal and stealing his short sleeve polo.

No big deal.

At least you didn’t shit your pants or get arrested. True.

From my vantage point, however, it felt far different. The reason why is simple: I had created this perfect dream scenario in my head of how the date was supposed to go. I knew the girl. She knew me. The stars had finally aligned. I’d gone on many dates before (and have since. Granted, I’m married now and have young kids. What’s a date again?), but never had I ever bombed like that. Never had the aligned stars screamed in agony as they rained down catastrophe onto planet Earth.

Which is why it has taken me roughly seventeen years to climb out from the crater in the aftermath and share my story of the worst date ever with the world. Hello, to my readers in Tunisia and Germany et al.

So, in conclusion, world-renowned dating expert, Dionne Smith, who studied at the University of Sydney, is right. What makes a good date is simple: instant attraction, good conversation, shared interests, and eye contact.

Don’t make it more complicated than it has to be. Don’t imagine a dream scenario. Don’t set yourself up for failure. And, I’d add one more: be yourself. That’s why your date was likely attracted to you in the first place.

And, if all else fails, consider King Boo’s advice from the reputable Yahoo! Answers archive of wisdom. Have a friend dress up as a ghost or a monster or something, and take your date to a haunted house, then save her.

Just don’t wear a sweater if it’s eighty five degrees out.

9 replies on “The single worst date of my life, aka: First, last date; otherwise known as Never reserve a ‘Table for Two’ at Red Lobster”

I read this out loud to my husband and daughter. We thoroughly enjoyed it! We laughed so hard, I had tears streaming down my face! Thanks for sharing! I always enjoy all your blog:)

I laughed so much while reading this, I had tears in my eyes! Thanks for sharing your stories, I thoroughly enjoy them.

I also remember a date you were on and your your very 1st car with a stick shift died right there in the parking lot of a Restaurant on Wards Road; I’m thinking it was Olive Garden. Your dad and I had to come to Lynchburg to pick you and your date up!

Oh, yeah. I forgot about that one. Her name was Brandi. Another fine dining experience at a chain restaurant. I’m sure we had the unlimited breadsticks while we waited.

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