True Story: Worst First Date Ever!

I am sure someone has a worse story – but I think mine would make the top ten list, if there is such a list. I was single and in my late 20s, that age where people were wondering about me – if I would ever marry, did I want to marry, what was wrong with me? – little things like that. 🧐 I did hope to marry and thought I had found the guy. He was just unaware of it.

William (not his real name) was the lead singer/guitarist of a local Christian band. We became friends. Kinda’. Not close friends but we had things in common. He played in a band; I played in a band. He was a guitar player; I was a guitar player. He wrote songs; I wrote songs; He was athletic; I was athletic. He had blue eyes; I had blue eyes. He loved Jesus; I loved Jesus. He was knock out handsome; I was . . . well . . . I was a little cute. 🙂 I liked him immediately. But everyone liked William because he was so likeable! For the three years we lived in the same building, I watched him date a few different girls but no one steady. I dated a few guys but no one steady. I was such a good friend to him that for those three years, I took William out to eat on his birthday – just the two of us. We were friends. And I was secretly in love with him. I believed one day he would look at me and say, “Deb, I just now realized that you are the woman of my dreams. Let’s get married.” And I would say, “What took you so long?” And it would be the story we would tell our children. 🤗

Then one day, his good friend Barbie (not her real name) asked me if I would like to join Ken (her boyfriend, not his real name) and Dick (not his real name) and his girlfriend Jane (not her real name) and William and go to a jazz concert together.

I was thrilled! I was obviously to be William’s date and I thought to myself “This is it!” I really did . . . I really did think it would be the beginning of a beautiful relationship. 🙁

The night of the concert I took longer than usual picking out my clothes. I needed to be hip and cool and yet casual and classy. After three outfits, I wound up with a blue shirt, blue pin-striped jeans and two skinny belts, one red and one white, to jazz it up. It was the 80s and the style was to wear multiple, colorful skinny belts. I had tried a third blue one but at the last moment decided it was too much. At 7:00, Barbie knocked on my door. She took one look at me, noticed my belts and said, “You couldn’t decide which one to wear?” And she laughed. And I laughed. But inside my gut seized up. Barbie, Miss Perfect, just told me I looked ridiculous. At least that’s what I heard her say.

We walked to the car where Dick sat behind the wheel and Jane was seated next to him. Ken was in the back with William. Barbie sat next to Ken, which meant I would be up front next to Jane. Oh well, I thought. William and I would surely be seated together at the arena. The conversations took off and I soon forgot my awkwardness earlier. Afterall, I was with friends. I had known Dick and Jane and Barbie and Ken for years, although I had never really been anywhere with any of them.

It wasn’t long before we were headed into a neighborhood, and I heard William give Dick directions to someone’s house. As we pulled into a driveway, William got out and said, “I’ll meet you guys there.” And then he turned around and mouthed, “Hopefully.”  And we pulled away and they all laughed.

“What are we doing here?” I asked.

“Oh,” Ken said. “William is going to be riding with Mary (not her real name) and we will meet them there.”

“Who’s Mary?” I asked.

“William’s date,” Barbie said. “At least he thinks it’s a date. This is the first time he has asked her out and he wasn’t quite sure she said yes.”

“How can he not know?” Dick said and they all laughed again.

But I didn’t laugh. I couldn’t breathe. William was bringing Mary. So I was nobody’s date. What was I doing there? I have never felt so stupid.

Until Barbie asked me, “Do you have any of Winston Marsalis’ records?”

“Who?” I said.

“Winston Marsalis. The guy we are going to see tonight,” she said with her eyes bulging.

“Oh,” I managed to whisper. “No.”

“I thought you said you liked jazz,” Barbie said. And then she turned to Ken, and they started laughing, and since then I have never felt more stupid. 😢 Not ever. Since that moment. What was I doing there? How would I survive the night?

We drove to Chrysler Hall and found our seats. Dick sat next to Jane who sat next to Barbie who sat next to Ken who sat next to William who sat next to Mary who sat next to me. The concert lasted ten hours. No, not really. 😏 It just felt like it lasted ten hours. I barely heard the music. I was fighting too hard not to let tears fall down my face, my heart absolutely crushed. 😞

That was the night I gave up William. He would never be my boyfriend. I had never been so wrong about a guy.

Until a few years later when I saw a handsome, dark-haired young man named Mark sitting at a nearby table.  He glanced my way and smiled. Hmm. I thought. Then he stood up—all six foot five inches of him unfolded out of his chair. And I shook my head and said, “No. He’s too tall.”

I was wrong about that guy, too. 😉

7 Comments on “True Story: Worst First Date Ever!”

  1. I had never heard this story before. This was great. Thanks for sharing. And, no, I’m not going to share any of mine. 😊

  2. I. Love. This. Not the agony of the “date” but your wonderful account of the whole thing. And I love you and Mark. Glad you were wrong about him. Y’all are a great team.

  3. This story is new to me. Aren’t we glad we survived all of those early dating years!!
    You’re braver than I am……not sharing.

  4. Your courageous introspection made me experience a revival of repressed memories of the many horror stories others could tell of my first visits with them. I thank God for the joy given me by my wife of fifty-five years who somehow either forgot–or forgives–my earliest blunders at expressing my love for her. Keep on telling your story as it helps others to revisit their own.

  5. Thanks for your vulnerability in sharing what was a painful story. I have a few painful ones I could share but won’t divulge the extent of my stupidity and some of them were far worse than yours😂. I am glad you ended up with Mark. He was a much better find than William❤️

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