My Worst Date
My Worst Date

My Worst Date

by Ruthie Hanson 2 years ago in dating

And My First Valentine's Day

My Worst Date
High school, 2007.

Let me start with a little context. I was queen of the nerds throughout my four years of public charter high school. Which meant that, while I enjoyed the relationships I did have, most of my dates weren't exactly chiseled out of marble, and when you're a pubescent teenager coming to terms with sexuality, there are the occasional fantasies of "the hot boy/girlfriend."

And then I met Frankie. I won't be changing his name because I doubt he even remembers who I am, and "Frankie" is such a fitting name for the story at hand. Let's start at the beginning.

I have no idea how I met Frankie. Like an amorphous ooze, he just sort of slipped into the cracks of my life. One day I didn't know him, the next day I did. And he was very, very pretty.

Allow me to frame my memory of him through my sixteen-year-old eyes: Tall, sculpted muscles, rich brown skin, sakura branch tattoos, and long, luscious, beautiful black hair. He was the hottest thing I could touch within a ten mile radius, and he was into me. We went on our first date and walked around the mall (I think we held hands? Maybe?). From this first date, there were two things I discerned about Frankie:

1) He always tasted like watermelon gum (hence the image), and 2) He was exceptionally stupid.

That last one hit home about halfway through our first date when we sat on the bench. He'd been rambling on about some conspiracy theory (he was into those) and I was only half listening. Then, all of the sudden, he looked up in the sky, and with wide, unironic eyes, he stated, "You know? The world... it's just so big."

I immediately knew I would not be procreating with this individual.

Anyway, we keep in touch for a few weeks. In my mind, I delegated Frankie to "hot arm candy" and nothing more, which was for the best in all respects—I neglected to mention earlier that he was 20 and I was 16. I promise, nothing illegal went down. So we text and chat, and one day, I realize that the upcoming Saturday is Valentine's Day.

Here's another bit of context for you: even though I went through high school boys like tissue paper, I was always alone on Valentine's day. I pretended it was no big deal, but I'm a sap, and the idea of having a special someone to give you candy made me all gooey inside. So, I bring it up one day, and he asks me what I want to do. I suggest something easy and cheap, like ice cream. He agrees.

The night before arrives. We have our usual phone call and he tells me that he has shaved off his glorious black hair, and gives me no reason as to why. I am just sitting there, a little stunned, not sure of what to say. Of course, I am very disappointed that that sweet, black licorice was gone from this world, so without thinking I say, "So wear a hat?" The conversation doesn't last long after that.

Valentine's Day is here. Now I'm fairly lazy when it comes to makeup, but back in high school, I gave precisely zero fucks—jeans and t-shirts forever. Today, I make an effort. I wear a nice top to show off my early-developed cleavage, I put on a powdered face, let down my hair, and actually wear heels. I am waiting about a half hour before his car rolls up to my front door and honks for me to come outside.

And thus the nightmare begins.

First red flag: The minute I get into the car, I don't hear a word of compliment. Hetero gentlemen, allow me to give you advice—when your lady has done herself up for a date, even if it's something small, tell her how nice she looks. Otherwise, it feels like we're ignored. But this was a minor warning sign, so I didn't pay attention to it.

Second red flag: Having never had a proper Valentine's Day before, I didn't know if I should get him anything, since the girls usually get chocolates and stuff. So I went to a bookstore and bought a book on conspiracy theories with my babysitting money. I hand it to him, he says thank you, and follows with, "Yours is on the dashboard." Sitting in the sun, melting in its wrapper, is a 97¢ Dove chocolate bar. A little blindsided, I pick it up and look at it.

"Is this it?" I ask.

He turns to me, point blank, and asks, "What, did you want more?"

It is at this point I start making up excuses in my head. Oh, he's probably surprising me with a nice lunch. He's probably saving money to treat me later. Don't be greedy, it's still a nice gesture.

Third red flag: He starts driving in the opposite direction of the ice cream place we previously agreed upon. He doesn't tell me where we're going.

Yup, he's definitely going to surprise me with something nice.

Fourth red flag: In a bizarre move, he points to what I believe is a stop sign or bus stop sign and says, "Hahaha, look at that guy. He's naked."

Or he's on drugs.

Fifth and BIGGEST red flag: He has now taken me across town into an area I do not recognize in the slightest. I'm starting to wonder if my decapitated head is going to end up on the evening news. And then, this TWENTY YEAR OLD MAN drives me INTO THE PARKING LOT OF AN ELEMENTARY SCHOOL and, as he parks, he says, and I'm quoting here, "THIS IS MY FAVORITE PLACE TO BE."


So here we are—a legal minor with a legal adult, alone in a car in the parking lot of an elementary school which the legal adult seems to visit on the reg.

I am definitely about to die.

"Oh! I forgot, I have something for you!" He reaches back behind his seat, and immediately my bullshit excuses start flooding in.

Oh, this must be his old school that he has great memories from! He's going to give me flowers and tell me some sweet story about how he had some of his best memories here and he wanted to share them with me! Right?


Frankie, after reaching behind him, pulls out what I could only describe at the time as a bag of black. Just black.

"Here you go." He hands me this ziplock baggie and I'm staring at it, trying to figure out what I'm looking at.

"What is this? What am I—oh my god this is your hair."

He gave me a plastic bag of his shaved hair as a Valentine's gift.

Frankie begins to laugh like it is the funniest thing in the world.

Appalled, embarrassed, confused, and a little scared, I finally demand that Frankie take me home. His laughter dies, and he looks incredibly confused, but he thankfully obliges. We drive in total silence, and at a red light, without a shred of self awareness, he turns to me and asks:

"Why are you doing this to me?"

A year later, he called my number to see if my mom could score him weed.


Ruthie Hanson
Ruthie Hanson
Read next: 'Chocolate Kisses'