Your Awful Stories: Three Tales of Assholes

An example of an asshole.

An example of an asshole.

There are myriad ways that men can act like assholes on an internet date. They can call you the wrong name, ditch you for a clearly fake emergency, or just maybe just barf all over the place. Hell, there are myriad ways that I’ve acted like an asshole on an internet date. One time when I was kissing a girl hello, I leaned in with such excessive enthusiasm that we banged cheekbones, and she said, with no small anger in her voice: “God! That really hurt!” OK, maybe that was more “ass” than “asshole,” but it was so profoundly lame that it certainly warrants the four additional letters.

Today I’m gonna do something I haven’t in a while, and that’s feature letters from you readers. I’ve been holding off because I only like to do it when they’re some serious doozies, and this batch certainly qualifies. All of these are messages from women detailing the idiocy, incompetence and general insanity that is the male internet dater. This is not say that all us guys are buffoons, some of us handle things just fine. I imagine. I really wouldn’t know. I’m pretty much 100% buffoon.


First, this month’s bronze medal winner, from Allie K. in Toronto, Ontario…

I’m sending you this ridiculous message from okcupid that this scary, scary individual sent me a couple of weeks ago. Here goes…

“hey whats up? you definitely seem ambitious and willing to take risks and now days its really hard to find that in a woman…well let me tell you about myself…i went to school at university of new mexico, where i graduated with bachelors of science in chemistry and biology…my parents moved down to Canada in february, so when i graduated i went and visited them…over the break my mom fell ill, they found a lump near her breast and thought it was breast cancer, but after the proper tests , they removed the lump and it wasnt anything serious…than a week or two later, we found out that her uterus had fibroids, so we opted for a hysterectomy, and during surgery they a 3lb tumor hidden behind her uterus. talk about a miracle story! ive been going back and forth from the states and canada…still trying to decide what is a better option for me…im not a guy who looks for sympathy, because sympathy is for the weak…i consider myself a beast, and it suits me well…

Rarely seen on a Valentine's Day card...

Rarely seen on a Valentine’s Day card…

Little tip, fellahs. If you’re ever wondering whether it’s appropriate to use the words “fibroid,” “hysterectomy,” or “three-pound tumor hidden behind her uterus” in an OkCupid email, the answer is no. It’s not appropriate. Look, I don’t mean to make fun, obviously the guy has been through a lot, but introductory dating emails are supposed to be fun, witty, and charming. And your mom’s gigantic tumor is none of these things. No one has ever said the sentence, “Hey, let me tell you this hilarious story about the cancer in my mom’s uterus!” OK, go ahead and insist that you’re not looking for sympathy, but 1) I don’t believe you, and 2) why the hell else would you possibly be telling this story?! Trust me dude, go with sympathy! It’s the only thing that makes sense!


The silver medal email from Ann C. in Dallas, Texas.

“Matt” had very cute pictures and was a real southern boy, something I always find endearing. Self described as athletic and toned, after several emails we decided to meet at 9pm drink or two. We meet, and first warning sign: he was not athletic and toned. I don’t mind a few extra pounds, we all have them, but he was about 50-75 pounds more than his photos. Oh well, I thought, maybe he has an awesome personality….

So we grab a table and Matt proceeds to order dinner, and insists I do as well. I explained we made the date at 9, and I had already eaten earlier at work. He asks I at least get an “App,” so he doesn’t have to eat alone. [Editor’s Note: You know what you should do when you’re uncomfortable about eating alone? NOT EAT.] Anyway, I agree, and order a salad despite not being hungry. Matt orders himself two dinners: a large fish dinner and a chicken meal. I now realize why he no longer looks like his pictures. He begins to eat, and I finish about half my salad. He orders 3 more drinks… not for me, for himself.  The waitress comes over, and asks if I would like the salad wrapped up. I say no thanks, but Matt jumps in. “Excuse ME , actually you can wrap that up, I’ll take it home, since I’m PAYing for it.” Who takes home a girl’s half eaten salad?!

thanksgiving_dinner.jpg.scaled500Matt finishes his meal and takes home my half-eaten salad. As the bill comes, he quickly takes it away and I offer to pay. He looks at me as if I am nuts, but I’m thinking “well sir, you’re the one who just made a huge deal about the salad and paying in front of the waitress!” After paying, he walks me to my car and I thank him for the 2 drinks and “App,” and say goodnight. But Matt isn’t finished. “Is that it? I bought you an $80 meal and you’re not going to come home with me?” I guess I looked at him in disgust , and he tried to throw in a ” Just kidding!” My salad was $6 and my two drinks were $8, so no sir, you did not spend $80 bucks on me! I quickly closed the door and drove off.

Two days later, he sends a text message:” Are you ignoring me?” I decided to respond: “Yes.”  I haven’t heard from him since.

The bad ones always follow up, don’t they? Not once have they realized “Well, that was a nightmare. No way in hell she wants to hear from me again!” However, as bad ones go, Matt would’ve had to order 50 entrees to compete with our gold medal winner. 


And finally, the gold medal story of male insanity, from Gail C., writing from an undisclosed location. With good reason.

It all started when I innocently met a guy for coffee on his lunch break. I did not plan on seeing him again, but he continued to text and call and I finally caved in. Several months went by of us hanging out and dating and spending time together. He seemed nice enough and harmless (HA). 

After some time I invited this guy, we’ll call him Steve, to come on a beach trip with my friends, but made it clear that we would have separate bedrooms, and he was only invited to stay two days, as I felt it was too soon to spend an entire week together. We drove there together when the time came and everything was fine for the first day.

The second night he was there, we were all drinking, of course. Steve became incredibly drunk, also of course. I told the others that I wanted some time alone and was walking to the ocean and would be back shortly. That is apparently where I went wrong. I was standing in the edge of the tide alone (approx. midnight), when Steve appeared next to me. He was drunk and angry at me for “running away”. He began bumping into me and standing in front of me. He was stumbling all around, so I took off running into the ocean to get away from him. The farther out I went, the more panicked he became. He was screaming at me to come in before the sharks ate me. I was just laughing and telling him to relax. I swam back to the beach.

"Do you know that I LOVE YOU?"

“Do you know that I LOVE YOU?”

At this point, Steve declares his love for me. “Do you not know that I LOVE YOU?” He then asks me to hold his new iPhone so he can go into the ocean to die, because he wants to die if I do not love him back. I realize this is serious, and head back to the house (running) to get away from him and to be close to my friends. I then go into my room, lock both the inside and the patio doors and text my friends to tell them about this whacko. [Editor’s Note: I’m sure her friends were real pumped to get that text. “Oh, she locked herself in her room, so I guess we get to deal with him all night!”] When Steve gets back, I hear him enter the house sloppy and clumsy. He is stomping and falling. He climbs the three flights of stairs to my room and I hear him tugging on the door knob. When it doesn’t budge, he runs to the patio door and repeatedly tries jerking it open. With no luck, he returns to the inside door. He begins knocking. Louder, louder, louder. My friends come up and tell him to go to bed like everyone else. 

My silence sends him over the edge and he begins banging on my door, and screaming “FUCK YOU!” repeatedly, and throwing things around the house. Not sure what else to do, I just try to sleep. As I am dozing off, I hear him stomping and slamming and him screaming my name “GAIL!” through the house and off the balconies. I finally fall asleep anyway, and am awakened nearly an hour later by loud pounding on my door. I try to ignore it and act as though I am not in there, and then I hear “Gail! Open up! It’s the Sheriff!”.

I climb out of bed, trying to decide whether this is Steve trying to trick me out of my safe place. I fling the door opened, pissed, only to find myself face to face with the Sheriff. Apparently Steve had been running up and down the beach screaming my name, and screaming for help. Another house nearly a mile up the beach had heard his cries for help and called the police, who immediately drove up the beach looking for a person screaming help. They found him on our front steps, and when asked if he needed help he responded “Yes! I can’t find my girlfriend! She was on the beach and now she’s in the ocean!”

The sheriff ordered him to go to bed, took me aside, and advised me to stop seeing him (duh). The next day, at 7 am, I woke up and informed him that he would be taking a taxi to the airport.

You know you’re in the middle of an amazing internet dating experience when you hear the words “Open Up! It’s the Sheriff!” So there you have it, Steve, Matt, and Mister Hysterectomy, showing the diaspora of male internet dating insanity. A little bit of crazy, a little bit of angry, and a whole lot of horribly confused. I will say that it’s not wise to invite a guy on a beach vacation if you’re not particularly interested in him, but it’s hard to blame the ladies on this one. Sometimes us guys, well, we just act like assholes.

Another example of an asshole.

Another example of an asshole.

Think your tales of internet dating disaster are medal worthy? Send me your awful stories here at! 

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12 Responses to Your Awful Stories: Three Tales of Assholes

  1. Brent says:

    Question: is it an “asshole” thing to do, not to pay for a girl’s drinks on the first date? I met up with a girl the other night at an expensive bar and bought her her first and her third drink (she bought her second), and we ended up making out afterwards, so I guess it was worth it, but I’m just a student and I can’t afford to go out and buy all these girl drinks all the time? Is it fair to split the bill on a first date? Also: have you ever heard of or considered that a girl might be working for a bar/restaurant, and getting into online dating just to bring customers to that bar/restaurant? Is that super paranoid? Thanks for any thoughts.

    • B says:

      Not at all, Brent. Read here:

      But, i would say that if you like the girl you should pick up the tab on the first date, because not doing so can be off-putting to a lot of women. If that’s difficult to afford, I’d recommend scouting out a few more reasonably priced spots. Plenty of great places serve $5 drinks, or look for a good happy hour that isn’t too crowded. I think it’s totally FAIR to split a first date, but it might leave your date a bit displeased.

      No, I doubt anyone would bring online dates to their bar just for customers, because if she hates you or you’re creepy, now you know where she works. But in general, it’s kind of a weird thing to do. Hard to feel comfortable when you’re so distinctly on someone else’s turf.

  2. Awkward says:

    Uh. You dated this guy for “several months” and didn’t want to spend a week with him/share a bed with him? Holy red flags, Batman. Next time dump him long before you get to the “vacationing together” stage. Sheesh.

  3. Amused says:

    So, B, here’s my question. Are assholes on dates exclusively male, or can women be assholes on a date too?

    • A says:

      Definitely, just see the gold story. From the way the writer herself depicted it, he might have been trashed, but she was the one being an asshole.

      • Amused says:

        I don’t know…

        B kind of alluded to “asshole” being exclusively male when he said “And finally, the gold medal story of male insanity”.

        Luckily, I’ve only been on one date where I felt the woman acted like an asshole, although it’s pretty tepid by INAM standards.

  4. Sams says:

    Bronze – That guy is just plain awkward. I don’t know if he’s necessarily an asshole.

    Silver – He might have been trying to be funny in an asshole kind of way. If he looked like his pictures, which she was into, it might have actually worked.

    Gold – He’s a sloppy drunk. That’s for sure. It sounds like a bizarre situation all around though. She didn’t want to see him again, but then did, not just once, but for several months. But he still wasn’t allowed to share a room with her? Or be together for a whole week? Bizarre.

  5. meganlyn says:

    That gold story is the epitome of the unreliable narrator. I’ve “caved in” to one additional date (benefit of the doubt and all that) but “several months”? That’s a relationship – maybe casual, sure, but still, there’s some level of familiarity and expectation. She gives lots of info on his weird behavior and glosses over what several months of “hanging out” entails on her end. There’s something hidden in here about boundaries and expectations and I don’t know what, but it sounds more like a guy who was led on (or whose delusional hope was encouraged through “several months” of seeing each other) then an asshole who didn’t know how to interact with a member of the opposite sex.

  6. betsy says:

    I kinda feel for the guy who got the Bronze; sure there’s the impression that he’s trying to get women to feel so sorry for him that they’ll go out with him, but there’s also the outside chance that he’s just a brutal over-sharer.

  7. jtp4250 says:

    The gold story is definitely crazy, but like everyone else, I don’t understand why she hung out with him for months….? It sounds like she was leading him on, or kind of messed in the head herself. Why hang out with someone you don’t like? I had an interesting situation (I’m a guy), it was nothing this crazy, but I think this girl is messed up, really messed up. Me and this girl went out once, a drink, kept in loose touch, then decided to meet up a few months later. Honestly, she was really my “type” per say, physically, but I thought she was cool. We liked a lot of the same stuff, were into sports. The second go around she met up with me with some friends of mine, good friends of mine and their wives (I’m 38). We were out Sunday watching the football games. She ingratiated herself to my friends, which I liked a lot, and was very friendly and talkative to them. They all liked her a lot and asked me what the story was and I was crazy not to pursue. I told them my reservations, that she was, as they all knew, someone what “plainer” than the girls I usually go out with, but agreed she was really cool. I figured what the hey, worst case I get a new cool friend…boy was I wrong.

    Short story, she didn’t want to date, which honestly, I was fine with. Like I said, she was into sports, an aspiring marathoner (I’ve run 5, I am training for my six). I even told her I was cool with this, and even asked her advice for some girls I was dating, I even offered to take her to a party I knew there’d be a lot of single guys, very close to her age (31), that should could meet, quality guys as well, I mean aren’t I the guy friend you want? Apparently, no. I was dumbfounded, but that is not what pissed me off. I should go back, not only did she ingratiate herself with my friends and their wives, she went as far as to start making tentative plans with them for the following weekend, which I thought was cool, I liked it. So, here was her response to my attempt, genuine attempt at forging a friendship, “We have nothing in common to even be friends.” ???? Then why do you text me? Why talk about sports? Why talk about running? Training? And the absolutely worst, why decide to hang out with me, someone you clearly do not like and respect, to meet MY friends, my REAL GOOD friends, and top of that, try to develop relationships with them???

    Is it me, or is this girl f’d up? I kept my cool with this little text exchange, I even said, if you don’t want to be friends, so be it, but after hanging with some people and some beer, one of my buddies texted something from my phone a little immature…it wasn’t terrible, just stupid. Not the way I’d want to go out, but not losing sleep over it. She surprisingly responded to it, I even asked, “why did you even bother? I even told her that honestly, I wasn’t upset, explained briefly the friend, and apologized.” She still kept yapping, all that crap, well, this ensures I made the right decision, which I responded…”ok. understood. no worries.”

  8. jtp4250 says:

    oo, can’t edit…”not my type” that should’ve been

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