Dates Where I Was On My Worst Behavior

As you have probably noticed, I have been on a lot of weird dates. Remember Sparkles? I do. Unfortunately. So in all fairness to the fallen soldiers that have attempted to date me, I figured it would only be fair if I shared some of the stories that the guys are probably sharing about me. Because really, have you been reading along here? I am far from normal myself.

So, since I am a confident and rarely embarrassed version of a single woman, I am not afraid to point out that sometimes I can be a pretty horrible and inexcusably awkward human being myself. Therefore, I bring you:

Tales Of Dating An Insane Woman: Dates Where I Was On My Worst Behavior

I tend to date a lot. Like, a lot, a lot. I usually have at least three or four boys on the “rotation,” giving all of them explicit instructions that I am not looking to settle down and encouraging them to date other people. You should see their faces. “So what are we,” they usually ask. “We are fun. That’s what we are buddy. Fun.” They are usually unamused. Why do they seem so surprised? I told them before our first date that I was not looking for a relationship, that I am, and will continue, to see other people, that I encourage them to do the same, and that I am not sleeping with them or anyone else.

Now seriously, who in their right mind would proceed into that mess? Let me tell you, a lot more than you would think. I have literally had this conversation several times before: “Well I’m busy tonight, but why don’t you take out that other girl that you were talking about and maybe we can meet up tomorrow.” You know what that is? That is ABNORMAL. That’s what that is right there. Abnormality at its finest.

Unfortunately, boys catch feelings a lot faster than I usually expect. Inevitably at some point, they want me to meet their families and label me “the girlfriend,” and then because I am a recovering emotional mess, I break it off completely.

But before that happens, stuff like this happens.

…..Sitting in a tree, K-I-S-S-I-N-G

I once went on a first date to the arboretum, which is essentially a highly overpriced forest preserve with trees that you aren’t allowed to touch. Unless you are me. So this dude convinces me to climb one of the trees with him. Unless it involves the highway or anything to do with my fish phobia, I am not one to back down from a challenge. I agree to climb this big tree, conveniently located right behind a large sign that says “Do Not Climb Trees Under Penalty of Law.” For some reason we have decided that this sign does not apply to us because we are adventurous idiots and with that we climb the tree. Once we are hanging out in the tree he starts to lose his balance a little bit. Now I will admit, I definitely have the better spot in the tree. My branches are like all baskety and nesty, and I’m chillen’ like a pimped out big bird, while he on the other hand, is hanging on to his side like a terrified baby monkey.

Now you wouldn’t be surprised at all to learn what happens next now would you? Of course not, because ITS ME!!! Weird stuff happens to me! So in keeping with my totally “of course that happened” life, the ground crew drives up in their little golf cart and starts trimming the lower branches of the tree. Poor date dude decides now would be the time to say “move over, I’m starting to slip (he didn’t seem overly alarmed),” and of course in my overly compassionate state, I’m all “DON’T MOVE OR WE MIGHT GET ARRESTED IF THEY SEE US.” There is only room for one of us in this nest buddy and I’m claiming it for the one without the manly muscles. Can you guess what happens next?

I kid you not, dude falls out of the tree. Boom. Just falls flat out of the tree. I think he may have even bounced a little bit, I’m not really sure, it all happened so fast. I will however, tell you what happened next. Dude bounced right up to his feet and starts talking to the ground crew. Clearly he is not gravely injured so naturally I seize the opportunity to jump out of the tree… and run away. All the way to my car.

See, I don’t need bail money, I just need to be able to run faster than dude guy. Success. That’s nice girl, what a sweetheart you are. You just abandoned your possibly, but probably not, gravely injured date, to save yourself. At least I was kind enough to text him and make sure that I didn’t need to bail him out. I didn’t and so the next date took place in a much safer location. I’m no longer dating him, but I’m pretty sure I’m known as the girl that abandon her date at the first sign of trouble. Oops.

Hello, I’m your debt. I mean date.

Now I can’t forget about the guy that I went mini golfing with. It was a first date and I didn’t know him all that well. If I had, I wouldn’t have gone. We walk up to the register to get the clubs and what not, and cheap ass just stands there. I tell the cashier that we would like to play one round, she gives us the total, and cheap ass just continues to stand there. Now I have my debit card in my pocket already because I fully intended to pay for myself, but come on cheap ass, are you kidding me? He doesn’t even move. I look at him and I ask “do you want me to get this?” to which he replies “that would be great thanks.” You’re kidding, right? Nope! I pay and decide this date is already over, but hello, I just paid, so hell if I’m leaving.

We get to the first hole and he decides he is going to putt first so he can “show me the correct positioning.” Well let me tell you cheap ass, I will never be showing you what positioning I prefer, because I will never be seeing you again after today. I watch him and then when its my turn I drive the ball right into the water trap. “Oh no baby, I’m not very good yet, would you mind getting that ball out of the slimy water for me?” That scenario was repeated for the first four holes and then I changed tactics and just became a complete bimbo. I’m dancing, cracking horribly corny jokes, and inviting everyone else on the course to play with us. He is keeping score, TAKING NOTES, constantly asking me to watch his swing, and then cheering for himself after every hole. On top of that he is fairly condescending, telling me why I, as a woman, will never be as good as him in life because he has a natural advantage. Thanks to him I have “lil dicky’s it’s a damn good day to be a white dude” song running through my head for the majority of the condescending date. When we FINALLY get to the end he asks me out to lunch. You know what? I could eat.

We get to the restaurant and he runs into a colleague, to whom he invites to sit down, and talks to for the majority of the meal. He never even once acknowledges my presence. No introduction, nothing. So since no one is noticing me, you won’t notice when I order everything on the menu then, right? Nope, doesn’t even notice. Once I’m finished with my childish inner temper tantrum and all of my meals, I leave. He texts me asking when we can get together again. Never. That’s when. The day after never. Maybe the day after your cheap ass finishes paying off the debt that I racked up at the restaurant.

How About We Move This, To The Pantry

Some poor guys don’t even have to do anything wrong to get a glimpse into the insanity that is me. One dude, we had been casually dating for a while, and we were sort of messing around in my kitchen. Now I never sleep with them, but as I’ve said before, I’m cool with messing around. So things are …”going,” and he picks me up and puts me on the kitchen counter. Now at this point, I have been giving him all the right ‘go ahead’ signal’s, highlighted by the fact that my hand is placed firmly on his junk, when he says to me in what he assumes will be a sexy turn on line, “I’m going to ravage you.” That’s it, my brain has now just flipped to past trauma’s. I slide off the counter without even saying a word while my brain is scrambling to process “What the hell were you thinking!? No one knows this guy is here, you are completely alone, AND KNOW ONE KNOWS IT.”

At some point I realize that I am backing away from him. I only realize this when I trip over something and land on my ass in the pantry. I snap out of trauma mode only to realize that the only person more terrified than me, is him. He looks white as a sheet. I feel awful, he feels awful, we continue to date, but I eventually break up with him because it just never feels not awkward anymore. Since he knew nothing about my past I most likely just appeared crazy to him. I’m sure that has made for a couple of great party stories.

Because I’m Just Awkward, That’s Why 

Now I don’t know about you, but me and my girlfriends love to gossip about the awkward moments in the bedroom. However, I have noticed that most of my girlfriends have conveniently been blessed with nothing but grace and poise in the bedroom and their dates seem to carry the burden of every cringe worthy moment. Or so they say…..

Not me. Have you read the description of my blog under the title? “A constant stream of over sharing…”

Yea. Get ready.

A couple of weeks ago I was making out with a guy in my car and he told me my gum didn’t have any flavor anymore. “My gum? How would you even know? Wait, I’m not even chewing gum. Wait, wasn’t I chewing gum? Speaking of…where is my gum? Oh my gosh, my gum is in your mouth!? Wth!” That has to make me officially like the worst kisser ever. Like, ever. I would be so grossed out if I were him.

Another time, in an even later date moment, I rolled over my boyfriend and fell out of the bed. That was hot. I bet that is a story he loves sharing. “Girl and I were getting it on and she just fell right out of the bed!” To be fair, only like %98 of me fell out of the bed. If memory serves me right, one foot was still tangled in the sheets, so I was only like mostly on the floor. I was a tiny bit still hanging from the bed, so only mostly on the floor. Not completely. That must count for something, am I right?

Or there was Black Friday where dude and I were doing a little more than shopping in the front seat of the car and my ass beeped the horn. Yep, that happened. It drew the attention of the entire packed parking lot to our near naked bodies pressed against the window at 2:30 in the morning. Classy. I, thought it was pretty funny. He, on the other hand, was mortified. Like I was laughing, and he was pulling my tree date moment and running for cover. To be accurate though he did push me against the horn. But whatever, I have no problem taking the blame.

Also, just for record, in case you ever need this info, those edible body paints that they sell at adult stores really should be called “shower paints.” I’m pretty sure that particular guy’s bedding set will be forever ruined thanks to the artsy flare that I had one night. Oops. I’d love to hear the explanation he gives to the next person who sees his now tye-dyed bedding.

Also, since I’m handing out info, don’t use whipped cream. Sounds fun, but actually, it really smells. Like its so gross it kills the mood completely. I feel bad that I made that guy run to walgreens at midnight, as I ended up literally gagging at one point. Nothing says “sexy” like a girl dry heaving! Stick with chocolate syrup. Trust me. You’re welcome.

I’m also fairly certain that I’ll never live down being the girl who went down on her boyfriend in his office only to find out later that his boss watched the entire thing on the security camera. Especially when I showed up the next day and his boss high-fived him. So naturally, just to mess with his boss, I showed up the following day as well, waited for his boss to walk by, winked at him, and then shut the office door. That time I covered up the security camera. I wouldn’t want to shatter the boss’s illusion he had of me as I sat in my boyfriend’s office and we did nothing but eat lunch.

Yea, I’ve had my moments… takes talent to be as awkward as me, just sayin’! So, as much as I love to rag on the boys for being weird and strange and awkward, I bring a pretty even game to the table.

So there karma, I am still allowed to make fun of my horrible dates because I am willing to also make fun of myself.

Maybe one day I will share with you the awkward bedroom moments that had nothing to do with me, because now take it from me, THOSE are funny. But in the meantime world, pray for the boys that take me out. They just have no idea what they might be in for.

Photo Credit Steamy Window:
Photo Credit No Sex:
Photo Credit Monkey:
Photo Credit Angel:

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  • Koro
    February 3, 2014 at 7:08 am

    One time when my ex-fiance and I were having sex, he had me on top. Granted I was still slightly inexperienced at this time so I was figuring out the rhythm. Anyway, he thought it would be funny to thrust his hips forward REALLY HARD. Besides nearly breaking me in two he launched me into the damn wall.

    • NotMyShametoBear
      February 3, 2014 at 1:01 pm

      Both parts of that sound incredibly painful lol!! Too funny though, I can’t even imagine haha!! Thanks for sharing!

  • Jon Snow
    February 3, 2014 at 3:18 pm

    This is the first time that clicking on random people links has been worth it , you are a pretty good writer and for what I read here a fun date. Best of luck to you.

    • NotMyShametoBear
      February 3, 2014 at 1:01 pm

      Well that’s a pretty cool compliment, thank you! Glad you stumbled on over here, hope to see you around here again!

  • Jennifer
    February 3, 2014 at 8:23 pm

    I don't like small, dark spaces or just generally confined spaces. I went on a date once to a really neat museum that had a HUGE model of the inside of your heart where you could walk around.Except the walkways were hallways and they were narrow. You absolutely could not get two people side by side in there. I'm pretty average weight-wise and I only had a couple of inches on either side of my arms. I took about four steps into the heart, then wigged out and bolted from the exhibit. I ended up sitting on a bench by the exit while my date waited for me. I didn't even tell him I was leaving. I just told him, “Nope, not doing small spaces” and ran out of the thing. When he came out, he hadn't even realized I wasn't behind him. Oy.Another time a date and I were walking around the park when he grabbed my shoulder and whispered into my ear, “Uh, Jen? Did your underwear just fall off?” I look down and yeah, there's a pair of underwear sticking out of the leg of my pants. They were clean, mind you. I'd pulled the pants out of the dryer and put them on as quickly as I could because I was running late. Guess I just didn't feel that a pair of underwear had made its way into one of the pant legs.Hooray for awkward dates!

    • NotMyShametoBear
      February 4, 2014 at 1:02 pm

      “Did your underwear fall off” Hahahahaha. I laughed so hard! “Yea, I have talent like that. I got my underwear off both legs, while wearing pants, and walking. You should see what I can do in the bedroom.”

  • Jon Snow
    February 4, 2014 at 3:12 am

    Sure thing, I go to CNN to read the trolling that goes with every “news” report, that's where I saw you posting your link. You would make a pretty good troll (is a compliment really).

    • NotMyShametoBear
      February 4, 2014 at 1:01 pm

      Hehe. I legit read the articles, but I figure “Hell, why not attach my blog link.”

      Apparently it works.


      Feel free to share it as well (Couldnt resist)

  • Jennifer
    February 4, 2014 at 4:02 am

    Remember Stupid Guy who thought he could drive from California to Hawaii? Yeah, this was that guy. It was our first date. I should have gotten the clue then.Love your response though. I was too busy being embarrassed to think up something witty at the time though.

    • NotMyShametoBear
      February 4, 2014 at 1:02 pm

      Oh gosh haha! Yea, he did seem like a bright one. Oh my gosh that is so funny!

  • Jon Snow
    February 4, 2014 at 1:20 pm

    I would but then people would be “Wow dude that explains so many things” and I would have to be like “no tard that's not me” either way I bet my reputation would be ruined >.>

    • NotMyShametoBear
      February 5, 2014 at 1:02 pm

      Eh, reputations are for people with self esteem issues. I make my own labels and I just force people to agree with them. 😉

  • Jon Snow
    February 5, 2014 at 5:06 pm

    Jokes aside, we all have self esteem issues to some level. Those labels like the were you claim to be crazy I'm going to have to disagree with you, you are highly intelligent very eloquent and sarcastic that you love to make fun of your dates doesnt make you crazy 😛

    • NotMyShametoBear
      February 6, 2014 at 1:02 pm

      Maybe I’m highly intelligent and bat shit crazy 😉

  • bearcat
    February 10, 2014 at 9:31 pm

    Pretty early in our relationship, I was joking around and told my boyfriend that I had broken every dick I'd ever come in contact with. Because I was being all jokey, he thought it wasn't actually true.Until he started to notice how accident-prone I was…I've fallen out of the bed onto my face. I also accidentally took a water bottle and smashed the end of his penis with it (I didn't see it there, oops!).Now “please don't break my dick” has become a running joke in our relationship. Even to the point where he's accidentally said in front of friends and now they all know that I've broken every dick I've ever touched.

    • NotMyShametoBear
      February 11, 2014 at 1:02 pm

      HAHAHAHAHA (take deep breath….) HAHAHAHA.

      Now I want to know how you broke the other dicks. That’s pretty awesome. Well, not for them, but I am enjoying the story!

      and also, how did you smash his penis with a water bottle! Was it lying on the table?? Hahaha, I am laughing so hard.

  • bearcat
    February 11, 2014 at 7:28 pm

    Water bottle smash was a case of both being naked in the bed facing (we're talking) and I'm getting really passionate about what I'm saying and taking the water bottle in my hand and stomping it on the bed for emphasis. And oops there's your penis, I forgot!I couldn't even begin to explain how I've broken every dick I've ever touched. Personally, I think they are easy to break (they aren't).I break most things. I usually get a new things that I really like and the first thing I think is “how pretty!” and the second thing is “I wonder when/how I'll break this.”I think he didn't think his penis would fall into the category of “thing I break” though…poor guy! He's a really amazing dude.

    • NotMyShametoBear
      February 11, 2014 at 1:03 pm

      That is so funny!! Glad he was understanding 🙂

      …..still laughing….

  • Anonymous
    April 27, 2014 at 8:09 pm

    OK, some of my male experiences for you..At 16, having sex with my first love. Music playing while we're having fun – his brother just walks into the room, without knocking – and who's on top? Me, all exposed…party's over for my said “boyfriend” and I. His brother rushes out of bedroom, my lover runs after his brother (with whatever piece of clothing on him)to tell him everything is alright, but he's gone. We didn't see his brother for days – and could he could never look me in the eye after that. Knock before entering…I go out with a guy, who's buying me drinks, then I see a guy I used to work with, spend the rest of the evening with him, leaving the other guy, and going home with said ex-co-worker…and having one of the best fool arounds ever…:)

  • Angie brenzikofer
    August 1, 2014 at 4:26 am

    I have two stories. First one just let it be a lesson to everyone. We were hanging out on the couch eating jalapeno chips. Then things got frisky. Then things, namely my vagina, started heating up. The oil on his fingers from the chips were setting me on fire. It was horrible lol. Always wash your hands! The second one is that we were out in the county, I was on the hood of his car, he was being very generous and was “eating out” when he stupid to say her could hear a car. I sit straight up and promptly slid right off the car since things were so slippery and wet down there. My ex was rolling on the ground laughing while I'm trying to pull my pants up before the car comes up to us. I was so embarrassed. I sit off that car so fast it was impressive.

    • NotMyShametoBear
      August 1, 2014 at 1:03 pm

      HAHAHAHAHA!!! Aw how funny. Thanks for sharing!

  • Anonymous
    September 16, 2014 at 6:33 pm

    Here here.

  • Nick Morozov
    October 11, 2015 at 6:14 am

    When you went out with the “golf guy”, did you take all that food to go?

    • NotMyShametoBear
      October 11, 2015 at 1:04 pm

      Hell yea lol!


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