My Worst Date
My Worst Date

The Worst (Best) Date I Never Went On

by Dez Riley 2 years ago in humor

How Being Tricked Into a Double Date with My Ex Led Me to the Love of My Life

The Worst (Best) Date I Never Went On

It was the summer after high school, where this story takes place. A small town just outside a city that was topping the charts for heroin abuse. I was 18-years-old and freshly out of the worst relationship of my life. After months of gas-lighting, emotional manipulation, suicide threats, all wrapped up in a bag of cheating, I was free. My mental health was soaring in comparison to how it'd been, and so when my friend's (Jana and Jacob) asked me if I wanted to go out to eat with them and catch a movie, I happily agreed. It wasn't until I was already in the car with them that they casually mentioned my ex was coming along.

In their own defense, I must add that they had no idea how bad our relationship had been. I told them we were on okay terms to avoid gossip, and they'd been friends with him for a while. I, in no way, blame them for the following disaster to come.

They picked him up as well, and the ride there was filled with puppy dog eyes and depressing comments about how he'd been. It was an exhaustingly common thing for him to do, and I had a bad feeling things were only going to get worse.

They did. He'd picked the place we would eat; his work. AKA the place where everyone already knew me and knew whatever he'd told them about the situation. The hostess was eerily smiley when we stepped inside, pushing us to the beginning of the queue and seating us almost immediately. The waitress happily asked if this was a double date, and her face was littered in confusion when I said no with a pointed look at him.

After the food arrived, they even dropped off a free dessert, claiming it was paid for by another table "for the loving couples." I didn't miss the way my ex gave me another puppy dog look at the words. I told her once again, we weren't a couple. My ex was quick to add, '"well, maybe someday" in a tone I wasn't thrilled about.

I excused myself to the bathroom. I'd debated slipping out the front door. I'd literally have rather walked the three miles home than dealt with this any longer, but who was at the door? His best friend of three years, claiming he was just outside for a smoke. The only problem? He didn't smoke. It hit me all at once—

I'd been set up.

Trudging back to my table in defeat, I looked at John with the most "help me" face I could pull. I was hoping that he'd noticed the awkwardness of this situation and give me a way out. He seemed to understand, and happily suggested inviting his friend Seth to the movie.

I'd met Seth once before, while my ex and I were still together but in the crumbling stages of the relationship. He'd been funny, charismatic, and had an itch for adventure that had been torn out of me by my ex. I was quite sure he'd find this situation entirely awkward, but I was desperate. I agreed, and Jana seemed happy to as well. My ex's face was filled with disappointment, but knowing he was outnumbered he reluctantly agreed.

Through retellings of this story, I later found out John gave absolutely no indications to Seth as to the shit-storm he was walking into. He claims it was because he didn't realize, but I entirely believe it was because Seth would have said no if he'd known. Not that I blame him.

We decided to pick Seth up instead of driving multiple cars, so away we went. He gave me a friendly smile when he opened the car door, and I thought I saw a hint of annoyance when he saw my ex. "You and me both," I thought.

I remember talking to him for the majority of the car ride. Jana and John were lost in conversation the way lovers get, and Seth was just as charismatic as I remembered—and twice as cute. Although in reality, I'd probably have talked to a hamster rather than my ex for another minute. My ex was happy to put in his opinions on the conversation, alternating between trying to befriend our new guest and trying to hold my hand or give me that ridiculous look.

On our walk inside the theater, I lagged behind. My ex did too, so I sped up. He did too, attempting to keep pace with me no matter what. John called for him, and thankfully he stepped forward to talk to him. Seth stayed behind with me.

"I thought you two broke up." He said inquisitively.

"We did." I replied in a dull tone.

He nodded, and I'd like to think of that moment as the moment he realized he was in over his head. Through buying the tickets (my ex tried to pay for mine, which he'd never offered while we were dating, and I sure wouldn't accept after) and taking our seats, my ex would not stop chattering to Seth. He took the open seat beside me, forcing Seth to sit next to him instead of the people he actually knew. In amusement I realized it seemed like he was trying to keep us from talking by chatting his ear off. Unfortunately, this lasted throughout the movie too. Every scene, there was a comment. It got to the point where I was hoping someone would complain so he'd get booted out. I don't even remember what movie it was because I couldn't remember anything about it because he was talking so damn much!

When we dropped Seth off, I got the feeling he'd probably hate me for that one. What a mess I'd put him through, right? He was probably laying in bed wondering what the fuck just happened. When I got dropped off, my ex tried to give me a kiss and was oddly surprised when I gave him a rude look and walked inside instead. I don't know HOW exactly he was surprised, given that I went out of my way at every given moment to express my lack of interest in another "second" chance. But I guess that's just the way some people are.

As for Seth, after a series of events, we're now living together, moving to another state within a few weeks, and are happily in love. So I guess I should be grateful for this absolute train wreck of a date.

(The names in this story have been changed to protect the privacy of the people involved.)

Dez Riley
Dez Riley
Read next: 'Chocolate Kisses'
Dez Riley

Follow me through these stories of life, humor, and lessons I've learned along the way. Along with some other stories of my life that I want noted.

See all posts by Dez Riley