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.

Paolo Sambrano, Oakland

Revenge Plan Backfires

There’s a little thing that I like to refer to as “The Ten-Year Revenge Plan.” Among me and my friends, it’s basically code for “how I’m going to fuck over my ex so that he’s so psychologically broken and emotionally dead inside that he’ll never be able to date or fuck or even look at anybody ever again for the rest of his life because of me.” It’s also commonly known as “winning,” and it’s a graceful art that we are all very good at.

For me, the ten-year revenge plan involved reappearing in the life of the boy I had dated for three years and hadn’t seen since we broke up fifteen months ago. Until he made that ten-year revenge plan a little bit too easy for me — you know, hitting me up on Facebook and saying things like, “Nothing makes more sense to me than you.” Which was, of course, my cue to commence the ten-year revenge plan.

At this point you might be wandering exactly what he did to warrant the execution of a ten-year revenge plan, but let’s just say that he’s my ex. That is the only thing you have to do to qualify for an attempted slaughter of your emotional stability and long-term happiness. It’s just like hunting: You don’t hunt the animals because you have a personal vendetta against them, you hunt them because they’re animals, and they’re meant to be shot and eaten. Just like exes.

So. I commenced the ten-year revenge plan by casually walking into his work one day, unannounced and unexpected, sashaying around his work, but the level of sexual ooze had been cranked down to “barely imperceptible.” Casual conversation, punctuated by inquisitive eye contact meant to gauge exactly how much “sense” I made to him. I left abruptly after what I would call a successful conversation.

Here, it should be noted, that a ten-year revenge plan takes a massive amount of patience. So, expectedly, it took a couple weeks before he messaged me on Facebook. But, like clockwork, he did, saying quasi-cryptic things that were meant to obscure the fact that I knew that he still wanted to fuck me. Of course, the whole wrench in the situation was the fact that, on Facebook, his relationship status stated that he had a girlfriend. And while it might sound like an oxymoron when I say I like to play fair while engaging in the ten-year revenge plan, I still had to ask right out, “Don’t you have a girlfriend?” to which he oh-so-nobly responded, “yes & no.” Cool. What a gentleman.

On to phase 2. Time to amp it up a notch. I had devised a plan to amicably attend one of the parties he was throwing at his work. The idea was that me and my friends would show up in a whirlwind, drink all the alcohol, make a mess, cause a scene, and in a flash of, “What the fuck just happened?” we would disappear back into the night just as easily as we came. I had anticipated that his current girlfriend would be there, which was all the better, because some casual afternoon Facebook stalking had revealed that his current girlfriend is, um … she’s just straight-up ugly. Especially compared to me, she’s got no ass, no style, no lips, a pinched nose, frizzy hair, and the overall look of boiled potato.

Really, the revelation that my ex was dating someone at least five steps less attractive than me (on a one to ten scale), well, this ten-year revenge plan might get cut down to two years!

All I really had to do was show up. I had scrubbed my stomach down and filled it with gin, gathered a gaggle of equally intoxicated friends, and stormed in. But sometimes the ten-year revenge plan doesn’t go as smoothly as you think it will. I flitted about the party, drinking wine and more wine, trying to set off an aura of casual gutter glamour as I childishly demanded he talk to me for a little bit longer than he had time to. My friends also descended down on the party like vultures to consume all the free wine that they could physically hold. All of us hit on as many people we could possibly squeeze into the proposed thirty minutes we planned on being there before heading back down into deep West Oakland for another ten hours of party-stalking and drug-chasing.

Until …. You know that hideous girlfriend I was talking about earlier? Well, it turns out that she has a drop of maturity in her, and in an “all white flags raised” gesture of camaraderie, she wanted to talk to me. To me! Me, the ex-girlfriend who has been called “evil,” “scary,” and “unapproachable.” (Yes, those are exact quotations, and I must admit I revel in them a bit.) But I was game, fuck it, why not, she’s just some scrawny white girl, and I was wasted enough to be cocky enough to think I could pull it off. It started out as an innocuous conversation about dumb little things. But, sigh, my morbid curiosity got the best of me.

“How long have you guys been together?”

“Three years.”

At which point, holy shit, did you know I can do math? Because I can, and I know that if I dumped this guy fifteen months ago, and they’ve been together three years …. This information was the amyl nitrate of turning sneering sarcasm into a twelve-second high of pure, uncut, unadulterated, unbearable rage. That lying piece of shit.

I guess it’s important to note here that what made me mad wasn’t the fact that he had cheated on me. I knew all along that he had been cheating on me, and, honestly, I wasn’t too piqued about that situation. It’s the lying. It’s the motherfucking lying that really pisses me off at the end of the day. It’s the lying, and the fact that, uuggghhhh, holy shit, if you’re gonna cheat on me, can’t you cheat on me with someone who’s hot?

“Excuse me,” I managed to get out from behind gritted teeth. And in true-to-form passion, I went up to the ex, and I’m sure you can imagine the type of shit storm that ensued. Me, in the middle of this burner-cum-graffiti-artist work party, screaming, drunk and, oh, dear, I’m afraid I did say some terrible things. I had descended into a blind fit of fury, blacking out on boiling blood as he dragged me outside to calm me down, where I promptly burst into tears and I’m pretty sure that my overabounding ego tried to punch him in the face several times.

There are a few snippets of that conversation that rattle woosily around my memory, most notably when I said, “I’ve fucked like a million people since we broke up, I even fucked a bunch of your friends.” A sentence which garnered a rather pleasing tirade of, “Wait, what? Who was it? Tell me!” But my absolute favorite thing that he said was, “You know I don’t love her. Of course I don’t love her.” Hah. Fuck your love.

Continuing, I’m sure, somewhat along those lines until he had to go back to the party he was throwing, at which point I mustered the courage to go back in and continue my high-brow level of balls-to-the-walls fuckery. I marched back in with my tear-strewn face and the only thing to do in that situation was to drink more.

I stumbled out to the back, assessed the present male population, and proudly said rather loudly, “Who wants to fuck me right now?”

I was still blind with alcohol and anger and tears, which worked out fine because it wasn’t really about anything other than dragging this guy up to the office and pounding out a vengeful five-minute fuck. Putting my panties back on as I slightly stumbled down the stairs, sussing out my tangled hair, grabbing a few bottles of wine, grabbing my friends, and let’s do this.

The rest of the night was pretty much a blur, but I’m sure that the two-inch bruise on my ass was from when I fell down a flight of stairs at that party behind Mama Buzz. It was just another night out partying in Oakland, kinda just like every other night out partying in Oakland.

I know I kinda fucked up that ten-year revenge plan, but that was six months ago and I am back on top of it. Maybe it’s going to be a ten-year-and-two-month revenge plan, what with that little setback, but I’m pretty good at this kind of stuff. Trust me, you’ll be seeing his rotten, bloated corpse stumbling around this city, and when you do, you’ll remember this story. I don’t really want to reveal too much, but let’s just say I’m successfully at phase 4, which entails a casual yet intellectually stimulating friendship with the ex.

As for that dude that I fucked in the office, I don’t think he understood that it was just fucking. Sorry, bro, if you thought our first “date” was awesome, but, surprise, I don’t even remember what you look like.

Pilar Reyes, Oakland

First Date #98 

#98 was my final Internet date. 

We chatted by email and over the phone a bit before meeting. I respected his life’s work as a top litigator, representing a cause dear to my heart. But jaded, I didn’t bother to get overly excited until we actually met face-to-face.

On the date I discovered he’s intelligent, interesting, not particularly funny, and not at all my type, but I wanted to give him a chance. Over three hours of dinner conversation, the top two hot topics that kept recurring were his ex-wife and his ex-girlfriend. From what I gathered, there was quite a bit of overlap. Dating tip for the fellas: Don’t lead with your past extramarital affairs. It’s not sexy to us.By the conclusion of dinner I’d learned what his favorite body parts of mine were (and neither of them happen to be my brain).

“I want to date you,” he said, “but I have a feeling you’re a real prude.” Huh! Cue to watch the date go sideways from there.

I was strangely insulted. He continued teasing me about my prudishness, I was kind of done with this date now. So I thanked him for the meal and said, “This prude has to go dance on a pole now.”


“Never you mind.”

“Can I come watch?”

“Only if we take separate cars. You can come, I guess. The club doesn’t open for another hour and a half.”

“We could go get a drink.”

“Fine, but only if we can go to Aunt Charlie’s.”

Aunt Charlie’s is this magnificent hole-in-the-wall, teeny-tiny dive bar catering to the LGBT crowd with drag queen revues on weekends. It’s awesome

I arrive after my date and he’s sitting at the far end of the bar. Between the front door and my date is a group of eight to ten gay men all chatting with each other. I push my way past them and join #98 for a quick one. 

He continues the berating of my character due to the prude flaw. And he pulls at my blouse to show me how I should wear it, if I wasn’t so prudish — and at his tugging the center top falls well below my bra. Finally, I’d had it with this guy. I turn around to my crowd of boys directly behind me (decorative bra showing and all) and announce, “It’s time for a poll! How many of you think I’m a prude?”

Cutie-pie boy #1 says, “Honey! In THOSE boots????? You — are not – a prude!”

The others follow suit. The committee ruled that I was not a prude. And on that high note, I stood up and said, “Thank you, my friends! Now, this prude has to excuse herself. She’s got to go dance on a pole at the Power Exchange.”

So I’m a pole dancer. I’m great at it. I can climb, flip, spin and more. I’m better than most of the “professionals.” 

The Power Exchange is San Francisco’s only sex club. It’s open Thursday through Sunday, 9 p.m.-5 a.m. Ladies (and trannies) get in for free — men pay big bucks. It’s not fair, I know.

The living room area of this club happens to be home to the Bay Area’s very best pole available to the public. It’s on a long, runway stage, is underlit, and has a backstage for practice. It’s two stories tall — it’s phenomenal. The large living room area looks a bit like the Red Devil Lounge. I like to go dance there on the occasional Thursday or Sunday, and I always go right at 9 p.m. when no one’s there.

The Power Exchange has many rooms — which I have not entered. I go there to dance, and I keep my clothes on while I’m dancing — I’m a prude that way. And, as mentioned above, the pole is located in what I would call the living room. Remember keg parties in college? Kids may have been kissing in the living room, but the real action always happened in the back bedrooms (or so we see in John Hughes films).

Well … it’s like that in this club. Center stage is me on a pole, and what else we’ve got going on there is usually some sort of deal-making session or transaction. In other words, the living room is mostly talk, not a lot of action.

As I warm up, I do harder and harder tricks, including some new moves I’ve been working on. Finally, when my body’s at full strength, I head down the runway and out to the center pole. I climb fifteen feet in the air and begin spinning, hanging upside down, having a blast!

About thirty minutes into dancing, I’m up in the air, and I’m inadvertently looking eye level at someone in the second story seating gallery, and I realize he’s caught my eye — so I quickly look away. I actually make it a point not to look at men in the club because I don’t want to accidently start something I have zero intention of finishing with them. It’s just protocol. 

So while I’m dangling fifteen feet in the air — upside down, mind you — I divert my eyes to somewhere safe. Normally, that would be down at the empty stage below me.

This time I choose to look over to my date … naked … completely naked … even his shoes and socks are off … looking up at me … and masturbating. Nice! 

All I can think is, “Dude! It’s the living room! I know it’s allowed and all, but it’s not cool!”Eventually I pop down off the pole, gather my bag off the stage and proceed to leave. 

“Wait!” he calls out, cock in hand.

“Um, no. You should stay. Have a nice time.”

“Wait, you can come over here and talk to me while I finish.”

“Nope, I didn’t sign up for this, I’m out. Have a good night.”

Second date? What do you think?

Wendy Newman, Oakland

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