Ten Inches of Disappointment

Hi again. Yes, I’m still alive. And yes, I know we’re almost entirely done with 2017 and I still have yet to update you on any dates from 2016.  But since I recently completely ended things with the guy I’d been regularly hooking up with for almost two full years, I’m too poor to go out until Christmas money starts coming in (really counting on you, fam), and the red wine I’m drinking is making me feel creative, I figured I’d finally brush the dust off these posts I’ve had drafted forever and send them off into the world.

As I’ve mentioned before, 2016 was a bit of a wild year for me and so only a few will be getting a dedicated blog post. But the ones I do post will be in chronological order… and fortunately, this first one is one of my all-time faves.  Prepare to be indulged.


Let me start by laying out the scene for you because this was not a pre-planned date or meet-up or anything of that sort. It was a Thursday night after work in January 2016, and I was getting ready to leave the bar I’d been drinking at for a fundraiser for the past few hours (funny enough, the fundraiser was hosted by the guy I mentioned I just ended things with, and this happened literally two weeks before we hooked up the first time). I was drunk, but nothing outrageous. My coworker friend left at the same time as me and she hopped in a cab while I continued walking by myself towards the subway which is how I decided I was going to get home. All of this I completely remember. Then…

Part 1: The Shortest Blackout of My Life

I must have blacked out for a total of 2 minutes tops. It could not have been more than that because next thing I know, I’m no more than 30 paces from the exit of the bar, and I’m making out with some random guy. On the sidewalk. No clue who this guy is. Never seen him in my life.


Since there was no one else around, I have to rely on what he said happened as truth. Apparently he saw that I had just left the bar to which he was headed, he asked me a question which is what got us talking… and then we started making out. Honestly, at the time I was so confused but also intrigued that I didn’t dig too much more into it. Plus, we continued making out on the sidewalk so that kind of limited conversation. I KNOW this makes no sense but he was super tall and a decent kisser, so I just went with it. That had literally been the shortest blackout of my life because from this point forward, I remember everything.

Part 2: From the Uber to the Park

I told him I had to get back home, and he said he had to go back as well.  Again, I really wasn’t wearing my Olivia Benson hat because otherwise I would’ve called his bullshit since he had just told me he had been on his way to the bar when we started talking. But I digress. So he ordered an Uber, saying he’d have it drop me off then continue on to his apartment. Since the plan was to go our separate ways, we swapped phone numbers then made out the entire ride to my neighborhood. I had the driver drop me off at the park near my apartment since I didn’t want him to know which building I lived in. Cuz yano, gotta look out for my safety.  Then he hops out of the car as well, and probably because I was super turned on at this point, I didn’t get creeped out at the fact that this guy was essentially following me. Cuz yano, I was clearly looking out for my safety.  We continued to make out on the park bench for a few minutes… then he decided he had something important to tell me.

Him: “I have a huge dick.”




Me: “Oh, uh, ok, did I just hear you correctly?”



Him: “Yes, I have a 10″ cock.”

Naturally, the only response I had to that was, “Ok, let’s see it.” So I took him back to my apartment to avoid the risk of arrest for indecent exposure. Cuz yano, safety.

Part 3: The Fun Begins

Once in my apartment, I took him immediately into my bedroom and closed the door.  He tore my top off, but I stopped him before he could get his hands on any other articles of clothes because there was a purpose he was there: I wanted to see this gigantic penis of his.  I made him remain standing, and my skepticism was building as I was unbuckling his belt because I wasn’t seeing or feeling anything yet. Pants drop. Still nothing. Boxers off… flaccid.


I’m not sure about any of you, but having a limp dick stare at you in the face when you were expecting this 10″ rod is not only disappointing but also super gross. They are not cute. It’s one thing when they’re only at least partially hard, but when the sucker is just dangling there lifelessly, then there is zero chance I will be doing anything with it. You gotta meet me at least part of the way there.

So with his pants and boxers still around his ankles, I stand up in front of him and ask, “Alright, where is it? I only see about two inches here.” His first plan of action was to begin aggressively jerking off tugging at his worm-like penis, but that had no effect at all. Next, he asked me to take my bra off; feeling bad for the guy/still wanting to see this ten-incher, I did just that and we made out against the wall for a bit. No luck. Still soft.

This brought him to his last attempt at trying to get hard: telling me to put my mouth on it.


For the record, I actually really don’t mind giving head to people who I’m hooking up with regularly and trust.  But strangers are a totally different story.  Now add in the fact that this stranger’s p was also soft, and it was enough to completely kill my DTF-status that night. It was time this ended.

I grabbed my shirt, put it back on, and immediately I saw the panic in his eyes that this might not be happening for him. Things turned savage pretty quickly.

Me: “It’s time that you go.”

Him: “No! I just need another minute!”

Me: “At this point, I have no reason to believe you are even close to 10 inches.”

Him: “I make girls cum like crazy, you have no idea.”

Me: *major eye roll at his last comment* “Congratulations but I’m ordering you an Uber.”

Him: “NO! You are so hot! I will die if I leave here tonight without fucking you!”

Me: “Please don’t die, but you are leaving.”

Him: “Let me go down on you, and then I’ll be ready to fuck you.”

Me: “Nahhh I’m all set.” *ordered him an Uber*

Fortunately, the Uber didn’t take too long to get there, and I managed to force this guy out the door. Unfortunately, I had given my number to him earlier in the Uber together. I’ve since deleted the texts, but based on his confident tone, he clearly did not pick up on the fact that he failed pretty miserably that night. After not responding to his persistent texts for about two weeks, I finally replied saying he must have the wrong number.


Despite that one and only reply, I continued to receive occasional messages from him as if I’d never said anything. Aside from one or two texts where he said he was going to be in the neighborhood and was going to stop by (thankfully, he never did), the rest of what he sent me were desperate attempts to get me to meet up with him. I kept my silence, and eventually he stopped trying.

So there you have it. This is what set the tone for my 2016 dating hookup single life.


Random Reflections on 2016

Sorry for all my bait-and-switch posts over the past, like, year. All year I’ve been talking up how amusing some of my encounters have been and how I’d be posting about them, aaaand now we are over halfway through 2017 and still nothing. I promise you the drafts are there and close to being done. But for one final tease – and because I’ve had this basically finished for months (no joke) – here is my annual (see 2014 and 2015) “Random Reflections” post.

Drumroll please…

1) Not having the ability to have feelings towards people leads to way more one night stands than prolonged hookups.

I kinda slept with a ton of people in 2016.  I’m completely fine with that, but considering the volume, I would have expected to have a lot more good sex. Now, in the defense of everyone, sometimes it takes more than just one go at it to have it be more mind-blowing. But, um. Do you know me? Right, I don’t have the willpower to continue anything with people I’m not into. If I’m actually into the person, then I’m way more willing to continue to hop in bed with him even if the first few attempts were less than satisfactory. But again, do you know me? I rarely like people, so this scenario very rarely plays out.

Take the flip side, though: if I’m not into someone but he was attractive enough that I slept with him and he rocked my body that first time, then, well, I won’t put up much of a fight to doing it again. I just will make it very clear it’s nothing more than a hookup because I will refuse to meet him anywhere except an apartment with a bed. If I’m just in it for the sex, then I don’t need to have drinks and try to force conversation with the guy; it’ll only ruin the mood for me. He just needs to tear my clothes off and keep doing his thing and that scenario will have me seeing him for more than a one night stand.

2) If you’re going to have one night stands, then might as well make the story good.

The best way to make a one night stand into a “good” story to tell later is for it to be just completely mind blowing sex. But lol. Rarely does that happen. Therefore, might as well make the story of what happened interesting, right?

I didn’t go into any of my one nighters with the expectation that they would be as, er, storytelling-worthy, but I definitely came out of 2016 with a hearty handful of them. I’ve mentioned a few of these as “posts to come” here, but looking back at my list of the year (yes, I have a list, whatever), there were quite a few interesting/unexplainable/bizarre/hot hookups that sadly may never make it to this blog for the sake of time and explicit content. Eh, there were also some that were just bad/mediocre and nothing else interesting about them, but I’d assume that’s to be expected.

3) Apparently I’m not picky about probably the only things I really should be picky about.

I just talked about how I had a lot of one nighters. Well, throughout pretty much the entire year, there was also one consistent guy. No, it wasn’t No Strings Attached guy – I actually only got with him one time in 2016; it was someone I haven’t made any mention of yet. I’m not going to get into the specifics of who it was for several reasons (who knows, maybe someday I’ll spill more beans about it), but my feelings were involved very early on.

Yep. And in the years since my last relationship (holy shit, it’s already been 6 full years?!), I can definitely say this is the most I’ve liked a guy since then.

Granted, the only two other guys who have pulled real feelings from me have been a guy who ditched me for someone else after just two months (update: they are getting married #goodluckchuck) and the guy from right after college who reappeared for a hot second two years later. So like, not much to compare this guy to. But there were real feelings involved, butterflies, insane attraction, you name it.

Now you’re probably asking yourself, “If Picky hooked up with him all year, then everything must have been practically perfect.” Yeah, you’d think so, right?! As far as looks go, he definitely meets my picky criteria. Personality-wise, I’m really close with him, he’s absolutely awesome, and I never get sick of hanging out with him. And the sex: obviously that’s been good, otherwise this over a year and a half long hooking up thing probably wouldn’t continue to be going on nearly as long.

So… what else should I have been picky about? I mean, over the last 6 years, those have really been the only areas on which I’ve gotten far enough along to lay any judgement. Ha. Well. Apparently I let the most important things go by the wayside, such as how he treats me and whether or not he wants the same things with me as I want with him. You know, like the most basic pieces of a relationship.

The thing is, he doesn’t treat me badly at all; he just doesn’t treat me with any romantic affection, especially with others around. And that’s because he doesn’t want a relationship with me (or anyone, he claims).

I know, I know. You don’t need to tell me. Why in the world have I been sticking around with someone for so long who doesn’t match up with those most critical things?! I’d say I don’t know, but I do. For one, I’ve never been friends with someone before getting hookups or feelings involved. It definitely throws a wrench into the machine. I don’t want to remove him from my life altogether because of the friends aspect, he meets all other seemingly impossible (albeit shallow) criteria, and we both are attracted to each other and enjoy hooking up with one another. This recipe has never been presented to me before ever. I’m not going to get into it too much right now (sorry), but it’s resulted in a repeating cycle of pure happiness, frustration, heartbreak, and excitement.

You’re hot. I’m hot. This whole thing is hot. Let’s keep this goooooing!

Consistent sex? LOVE IT.

Uh… that was annoying. But whatever. It’s cool.

It’s just like. Idk.

Oh boy. I’m starting to not like this.

Noooo I hate feelings….

I’m like. Sad.

Poor poor me.

Boyyyy what you doing ain’t cool.

But like meh. I’m a cool girl. I’m past it.

Is that a gun in your pocket or you just happy to see me?

Uh huh. That’s right. You want me.

Cuz I like totally want you too so let’s keep this goooooing.

And around and around we go. Sounds super fun, huh? Blah. Well, we are still hooking up (just a few months shy of two years) so perhaps you’ll hear more about it as time goes on. It is 110% certain that a committed relationship won’t be happening, but as long as the happiness outweighs the negative feelings then I suppose I’ll keep staying the course.

Aaaaand that’s a wrap.  Hope you all missed me. Cuz I’m back.

Most Memorable Dates of 2016

I’m starting to think that neglecting this blog is garnering the same type of bad karma as ghosting someone, so apologies to ya’ll who still come back here only to have the same disappointment I have as when I lob a clever AF message to a guy on Bumble who never actually responds. So I’m back! And with plenty to share…

lets do this

As I mentioned in my last Dating Chronicles post, I had my first real no strings attached hookup buddy towards the end of 2015. Seeing as that was practically another lifetime ago, I’ll update you now and tell ya that we hooked up once more in 2016, but he did not make this list since that’s just old news now.

The fun news is that there were a handful of dates and a ton of hookups that occurred in 2016 so those who made the list should truly be… proud?  The not-so-fun news is that since there is no chance I’ll have the time to share all of the stories that exist, this is all you are going to get for Picky’s whirlwind of 2016.  But I’m hoping what I do share will at least be amusing enough to kind of make up for lost time.

Soooo… not all of these have actually been written yet – but I promise there have been drafts created for months!  So in the meantime, I’m going to give you a preview of each, and you will have to stay tuned for the full version.

So here we go!

Fifth Place: My Personal Trainer

Looking back, I should’ve known he was into me by how much he enjoyed stretching me.  Sure enough, the second he quit the gym was the second he asked me out.


Fourth Place: My Uber Driver (read: A Whole New Meaning for Ride Sharing)

Turns out leaving a comment for your Uber driver is a great way to get asked out on a date.


Third Place: The Dirty-Talking French Lover

He was really into how much I reciprocated the dirty talk.  Until I said no.

that means no

Second Place: My Hawaiian Conquest in the Irish Castle

We started hooking up under the stars and ended in a 600-year-old castle in Ireland.


First Place: The Guy Who Just Couldn’t Deliver (read: Ten Inches of Disappointment)

Honestly, if you are going to talk the talk, then you better be able to walk the walk.

walk the talk

I’m going to try to get these published before the next millennium, but in the meantime I’ll also be publishing another annual Reflections post.  Stay tuned.