Thursday, February 13, 2014

Worst Dates & Size Matters

Day 4 and we're talking about small wieners. Seriously Kathy, you are too much sometimes. I cannot believe you are a mother. I love you for sharing this. 

I was going to discuss my worst experiences. That time I was licked from chin to ear. Literally, like a dog. That time I went on a date and he turned out to be gay. That time I went on a date and it went well until I spilled my Caesar and probably embarrassed him and never heard from him again. The time I made out with my bff's little brother's bff. And never lived it down. That time where I went on a date last weekend and kept telling him "I could be crazy you know". #StrangerDanger and let my friends spy on our date in case he turned out to be a murderer. I'll let you figure out how that one worked out for me. And he was really great too...

Anyway, Kathy's story is just too funny and ridiculous and it needs to be shared. So... I hope you aren't offended too easily (sorry mom). Here we go!


I was reading some funny dating mishap stories on the internet so at my expense, I thought I'd embarrass myself by sharing a story that happened many moons ago.

Back in my heyday, I dated a guy whom we'll call john because that was his real name.  he was nice and treated me well.  there were certain things about him that I shouldn't have overlooked but I was young and didn't acquire my jedi master dating skillz until much later.  I drew some crappy pictures to illustrate the story, but first, some history. 

I've always had dating deal-breakers; you know, those certain things about a person that changes your opinion of them and completely turns you off; basically killing whatever potential said relationship had.  i wasn't Jerry Seinfeld picky but I had my own set of preferences - no bad kissers, no chewbaccas, no shorty mcshorties, no dainty feet that could fit into my shoes, no virgins and no small wieners.  yes, I was that shallow in that I could not pursue a relationship if the guy was wielding a tootsie roll in his pants. don't judge. and because this is a funny story, I'm sure you can surmise where this tale going. 

back to john.  the initial stages of a relationship are always the most exciting and I didn't want to whore out by moving too fast so the clothes stayed on.  there are many ways to assess the situation "Down There" without directly touching anything and I pulled out all the stops to try and figure out what I was dealing with. the most surprising thing?  I felt nothing.  nada. zip. while the warning bells were going off in the back of my mind, I thought that maybe he was nervous so i ignored my bruised ego and chalked it up to initial jitters.


the next date was pretty much the same with confusion building in my mind instead of him building something in his pants.  what the fuck was going on here?  does he have that much self control?  is it me? is it him? what? WHATGODDAMMITWHAT?!?  but like the stupid little girl I was, I ignored it and continued on, giving him just one.more.chance before I ended it. there was no way I was going to sacrifice my self-confidence for someone who felt nothing for me. 


I went on our next date with a heavy heart and the sahari desert in my pants when things started looking up because lo' and behold, something bumped up against my hip - something substantial. I think I mentally high-fived myself; my ego was restored, all was right with the world and I was a sexy beast once again.

but my joy  was short-lived because John was behaving strangely; it was as if he wasn't comfortable with something because he fidgeted and squirmed so much that he stopped all the goodness and stood up.  I'll let the pictures tell the rest of the story.






Honestly, I'll admit it. Size matters to me. It does. There we go I said it. I know a lot of people say it's not the size of the vessel but the motion of the ocean but no. No thank you. I can't. And clearly Kathy agrees. 

Do you think size matters? Any funny/horrible dating stories? I'd love to hear it!


  1. that is great!! OMG dying over here, great story!!! I once went on a date with a stranger I met on AOL messenger (yea im showing my age) I was in my early 20s, we were meeting at a restuarant, this is before cell phones were as big as they are now. I was already at said restuarant and there I see him pull up....ON HIS 10 SPEED BIKE!!! yes a 20 yr old on his bike, helmet and pants stuck in his socks....yea...we didnt make it very far haaaaa

  2. This is awesome Kathy. I had a guy like that once. Needless to say once I saw his "tootsie roll" it was over faster than it began!

  3. Omg, the pictures. This was amazing! Kathy is too awesome.

    Okay, okay, I'll share my story. (Oh and for the record, yes, size matters.) So, I was with the guy once and we were uh, you know, in bed. There we were, about to get it on, when I looked at him and said, "Why aren't you hard yet?" To which he responded, "I am."


  4. HAHA Kathy this is SO hilarious, especially with the pictures!!

  5. oh man the paint shop pics just make it.

  6. This is hilarious.....I need to learn how to draw stick figures to act out my life stories like this ;-)

  7. This is the best dating story I've ever read. So hilarious! And it's true... size does matter! Not even sorry to say that.

  8. I was almost concerned this was NSFW, but it was perfect for work. haha and I agree with Kathy!

  9. BAHAHAHAHAHAHAHAHAHAHAH! I love Kathy so much it's borderline creepy!

  10. HA! can't say thats not a legit concern..

  11. I was seeing a guy that was small... and I think it might even be considered "micropeepee" in medial terms, but umm yeah, he tried so hard to get it in but i just thought... this is really pathetic and my sex drive just went down in 1 second when I found out how much he was struggling.