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  • Writer's pictureMatthew Scipioni

Parental Supervision: My Awkward First Date with a Chaperone

By Matthew Scipioni

Dear Matt,

With Valentine's Day coming up I was wondering if you could tell the story of your first date?




Dear Anonymous,

Well, it wasn't glamorous or spectacular, but if you want to know, you want to know. So here it goes. Picture me: 16 or 17 years old, still in high school with a girlfriend. Don't ask me how it happened because, honestly, I still don't really know. I've never really been good at the "dating" thing, but I wanted to spend time with this girl outside of school. I guess I thought that she was cool or whatever. Let's move on. I'm like, okay, nice. I'll give her a call (yes, people called each other back then) and set it up. We agreed that we would see a movie at night one weekend.

I didn't have my license then, so I had to figure out a way to get to her house. She didn't drive yet either, so I guess she asked her parents to drive, and I was like, "yeah, okay, sounds good." So naturally, the car ride to the movie theater was super awkward. It was her parents in the front and me and her in the back. Her parents asked me who I was and asked questions about myself. Great. So we get there, and her parents are also getting tickets! I was like, "oh, okay, sure?" not knowing that that was a little weird.

I'm ignorant. What can I say? After getting some snacks and drinks, we went to the theater and watched the movie. We didn't do anything, don't be weird. After the movie, we had planned on getting dinner, and again her parents joined us. That was also more than awkward, just the four of us sitting in a Five Guys Burgers and Fries. Let's see… after that, we made our way back to my house. I said goodnight to everyone and went inside. As I said, not anything crazy. In hindsight, I understand that her parents might have come to make sure she was safe and I wasn't crazy or anything, which I get. But also, in hindsight, it was kinda weird that they were there, like how in the world was that a normal thing to happen?

So there you have it, my first date. It was definitely an interesting first-date experience but not one that I would like to repeat. No disrespect to my girlfriend at the time; she's still cool. Moving on...what personal story of mine do you want to hear about next?




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