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Terrible, Horrible, Very Bad Dates

We asked; you answered: readers' worst-date stories.


We asked; you answered: readers' worst-date stories.

My Very First Date

(Note: The name of my date has been changed to protect his identity.)

I was seventeen years old, a senior in high school, and had put it off for way too long.

Stuck somewhere in between Weezer and the Misfits, I was a certifiable loner in high school and my "fuck the world/I'm so weird" state of mind certainly didn't help get me any gentleman callers. I spent much of my senior year browsing thrift stores for Little League shirts and watching reruns of Seinfeld. During school hours, I sequestered myself in the darkroom making art, or rather, developing photos of garbage and construction sites. To maximize my darkroom time, I signed up to be the teaching assistant for the graphics department, which is where I met Justin, a sophomore who decided to take graphics for his art elective and destroy my self esteem.

Stuck somewhere between an Abercrombie & Fitch bag and another Abercrombie & Fitch bag, Justin was on the high school crew team, which struck me as odd since I didn't know the high school had a crew team, and was just enough of a hottie to make me that uniquely adolescent combination of angry and uncomfortable. I was entrusted to help him with his screen-printing and film-developing and time-wasting. All was good and well until one day he asked me out on a date. And, to my surprise, I said yes.  

Since Justin barely had his permit, I picked him up at his house and we went for a walk on the beach. He spoke at length about the enlightening engagements of his bros and insisted I try doing a keg stand at least once in my life. It didn't take long for me to realize I had absolutely nothing in common with this person and began wondering how quickly I could get myself out of this situation. On the way back to his house, he asked if I'd like to talk for a bit longer in the car. I thought to myself, shit this is the part where we are supposed to make out or something. Bracing for what I thought would be the most awkward experience of my life, my first make-out session, I ended up completely unprepared for what actually happened.

He gazed in my general direction but not right at me, and I could tell he was preparing to say or do something that he didn't want to. Like taking me out on a date was some sort of charity work he could put on his college applications. Finally, he asked me the question that has gone on to define my adolescent life.

"Why do you dress so weird?"

This is really happening, I thought to myself. I was speechless. What could I possibly say to this person to express the pure and total shit of the situation?

"You'd be a really pretty girl if you dressed more normal."

Years later, another boy from high school would track me down and call me a "diamond in the rough." So apparently my potential was well-known amongst the popular boys in my school. If only my wardrobe wasn't holding me back.

"I mean, my friends were making fun of me for talking to you at lunch and ...."

The rest of that sentence was drowned out by the screeching of my tires.

I spent the drive back home with rethinking my entire identity. Maybe to get a boyfriend, I thought, one has to ditch the black on black on black and wear gender-appropriate tops. Maybe in order to be attractive to boys, I have to lose the eyeliner and consider blond highlights — seemed to work pretty well for most of the other girls in my Southern California high school. Years of self-doubt and insecurity had culminated into that one question said by that one boy on that one date that I didn't even want to go on to begin with. 

Then I thought, fuck the world, I'm weird, and who the fuck cares.  

EPILOGUE: Those high school traumas sure do find their way in and my ultimate fear of the word "date" comes from this experience. However, this story has a happy ending, and although I haven't been on many proper dates since, I sure have had a lot of great sex. Because in adult world, the whole "fuck the world/I'm weird" thing is currency. And I'm rich, baby.

Jessica Buffy Seipel, Berkeley

Don't Make Eye Contact

1) When I was in high school, I invited this girl I was really into to the first big theater performance I was in. It turns out that while I was onstage performing, she ended up making out with one of my best friends in the audience.

2) There was a random girl on the streets of Berkeley on a Saturday night who made eye contact with me. Me, trying to get over my crippling social anxiety, started a conversation with her. I ended up buying her coffee, and the fact that she was willing to talk to me and seemed evenly remotely interested in what I had to do made me overlook that there was something a little off with her. We end up walking down University, where the conversation shifted to food, where we end up in front of the Trader Joe's and then she proceeds to ask me point blank if I could buy her groceries. I decline, and the walk back to Shattuck turns into if I was ever given a helping hand when I was down. I say no (I lied). I bid her farewell and never see her again.