This Year’s Version of the Attractive Pompous Douchebag

Remember 2014’s infamous Pompous Douchebag? Remember how much he sucked, but yet, because I wanted to make out with him, he managed to get me to go on a second date? Well, this guy (who was my third happn date in March) is almost entirely the same tale… except no second date was necessary because I got what I wanted on the first round.

Let’s start from the beginning: a few days after the office stint with happn #2, I met up with this guy. I was really excited because his pictures depicted a man one year older than me who perfectly fit the mold of my ideal look. However, I was a little thrown off by the fact that he mentioned that his birthday was on the day of our date. Not a few days before or after his birthday… his actual birthday. I know I’m awesome, but I thought it was a little strange that he wanted to spend his birthday with a total stranger from the internet. Whatever, I used it as an excuse to pick up two cupcakes from this bakery I’d been wanting to stop into (don’t be fooled – the cupcakes were more for me than for him).

Right out of the gates, it was clear that his pictures were misleading. He was short. Like no more than half-an-inch-taller-than-me short. He was also very little in terms of his build, and I later came to learn it is because he never works out. Ever. Oh and get this: he lives LESS THAN ONE MILE from work… and he takes an Uber to work every single day. Not only is that lazy but, um, can you say surge prices up the wazoo at that hour?! Ridiculous. But to take a step back, as far as his looks go, I can’t really slap the “Kinda Catfish” dating problem stamp on him because his scruffy face looked like his pictures (which I was very pleased about) and happn doesn’t make you list your height or any other details like that. So all in all, I was disappointed BUT not completely uninterested.

allow it

I’m going to go through this date in two parts.  So let’s begin with the problems…

Problem #1: Juan Pablo Syndrome

Unlike last year’s Pompous Douchebag who was too cool to give me ANY details about himself, this guy took the completely opposite route. He had one of the worst cases of the Juan Pablo Syndrome ever. I kid you not, I learned everything about his childhood, how he dropped out of high school, all of his attempted entrepreneurial ventures, exactly everything he has done and is doing for work, how everything in his life is the best ever, and everything in between. I literally even knew the life story of both of his sisters, including what they were like growing up, what schools they went to, where they live, what they do, and even a decently detailed summary of their husbands’ lives. While the details have been discarded from my memory by now, I kid you not: I was able to reiterate in great detail the stories of his and his siblings’ lives to my friends the next day.

What did he learn about me from questions he asked (as opposed to me just telling him)? I can list it off for you: the name of the company I worked at, the fact that I have two siblings, and where I graduated college. That’s it. And that’s exactly what he knew; it’s not like he asked what I do at work, whether my siblings were brothers or sisters, or what I studied in college.

so much you dont know

Now, when someone has this dating problem, I typically just take note of it and wait until this blog to address it. But this guy was so terribly exactly like JP that I decided to call him out on it.

*He finally ran out of things to talk about and now there was an awkward silence.*

Him: So….

Me: So…. (letting the silence build to see if he would come up with a question)

Him: What do you have to say? (ahem, anyone else notice how similar this is to the Sex at Dawn convo with Pompous Douchebag?!)

Me: Well, do you have any questions for me? I feel like I know your entire life story but yet you know nothing about me.

Him: (very defensive) What is that supposed to mean? It’s not like this is an interview!

Me: I know. But I’m curious what questions you might have for me. You haven’t shown much interest in learning more about me or my life.

Him: (still very defensive-sounding) Ok, then tell me about yourself.

tell me about yourself

I thought that was an ironic question to ask since it’s such an interview-y question. Not to mention, it’s a total cop out. Whatever, I don’t remember exactly what I told him but I talked long enough to make it less awkward than it was when I called him out.

Problem #2: Pompous

If this guy and the original Pompous Douchebag were to go head-to-head to determine who was the most pompous, the original would probably win… but it would be close. Throughout his entire schpeel about his life, this guy somehow managed to make it sound as though everything he did in life was right while everything else is wrong.

im right youre wrong

Example 1: He dropped out of high school because he knew he a lot of the curriculum was unnecessary and that he could teach himself what was necessary better than the teachers could teach him. And people who follow the system are followers with no opinions or ideas of their own.

Hahaha, I specifically remember him saying that last line because I laughed out loud. Ok, so I will say that I admire the fact that he has come to have a successful position at a growing company all due to his own motivation and without a high school degree. That said, he could have told me this in a biiiiiiit more of a humble way.

Example 2: He worked at the best company ever. No, this was not the opinion of a very happy employee. This was an indisputable fact.

And he so generously offered to try to get me a job there because, you know, I’d obviously love it way more than my current job.

cool sarcastic thank you

Problem #3: Judge Judy

This kind of goes hand-in-hand with the pompous problem, but he judged the shit out of so many things that weren’t in line with his life. And the funny thing is that he had no basis for half of the things he judged.

For instance, he grew up in our current city, while I told him that I grew up in another U.S. city. He wasted no time to tell me that this city is so much better than my hometown and how he was so happy that’s not where he grew up. I was a bit shocked to hear this because it was so rude people tend to actually really like my hometown city, and so I asked if he had ever been there before. NOPE.

keep that mouth shut

Stay tuned for the second part of the date with tequila and sexy time…


The Movie-Referencing, Touchy-Feely Subway Kissing Stalker

Sorry for taking forever to update you all on my dating binge.  There are still plenty more posts to come after this, so I hope to not keep you waiting too long between each one.  In case I do, though, you can stay somewhat up-to-date with me by following me on Twitter (@ThePickyDater).  But without further ado, here is the breakdown of one of the first guys.

Unfortunately for this husky guy, he was walking into a losing battle because I wasn’t crazy attracted to him from the get-go. That’s probably a confusing statement because, well, I’m the Picky Dater and so whyyyy would I even consider going out with someone who was already doomed to fail? Ummm I just didn’t actually know who he was when I agreed to a date. Basically what happened was my horoscope at the beginning of the month (October) said that now is the time to get my sexy on so obvi I translated that to mean “aimlessly respond to any guy that messages me on OKCupid.” Pretty soon I was messaging back and forth with way too many guys, and that eventually led to us exchanging numbers and texting. The thing about going offline to texting is that suddenly all they are is a number to me. I don’t save guys’ numbers in my phone until at least the second date, mainly because it would be pointless to do so before I’m horrible at names and “Joe Schmo the Guy I’ve Never Met” has no place taking up memory on my phone. So I had at least 7 random phone numbers that were texting me and I wasn’t sure who each person was.

who are you

The only way I was sure was if I matched the name they gave me in their first text with the names of the people I’d given my number to on OKC – and that was clearly just way too much work. In the end, what got this guy the date was how straightforward he was about asking me out, followed by the exact time and location for our date. I totally loved that this guy took charge like that, so I agreed. Once I realized which guy it was, I was a little bummed but I was willing to give him a shot.

Problem #1: Pompous
When I say he was pompous, I mean it in a very different way than I did about the infamous Pompous Douchebag. And “pompous” might not even be the best word to describe him, but whatever, that’s what I’m going with. Anyways, the conversation we were having was okay, but it didn’t take long for me to realize that he was a HUGE fan of referencing movies, memes, you name it. It does take a certain level of wittiness to pull this off, and so I will tip my hat to him for this, um, “skill.” But the frequency at which he would reference movies was getting increasingly more annoying, especially when he started to quiz me on what movie it was that he just referenced. Then what really irritated me was what he did when I wouldn’t know what movie the line was from: he would call the bartender over and ask him to identify the origin of his reference – and go figure, the bartender almost always got it correct. It literally started to become a game to him, and soon my date and the bartender were bonding like the total hipsters they were over how they have seen way too many movies and how they couldn’t believe I didn’t know some of the movie references. This is no joke; the bartender actually ended up stationing himself right in front of us throughout most of the night in order to participate in this horrible game show of a date.

dont try making fun of me

Problem #2: First Date Check
Put simply, boys, it is in your best interest (if you like the girl, that is) to pay on the first date. That said, I have gotten a lot more understanding and forgiving about this problem when my date goes out of his way to meet up somewhere close to me. If you are taking extra time and/or money to make the date more convenient for me, then congratulations, I won’t judge you as much if you let me split the check with you. But in cases like this when my date chose the location which was conveniently down the block from him but a $22 one-way Uber ride for me, then I am going to be less than thrilled when you immediately accept my fake offer to pay or split the bill.

never seeing you again

Problem #3: Bad Kisser
I’m categorizing this under “Bad Kisser” not because he had no skills – actually, he was a pretty decent kisser – but it was the way that he went about the kisses (yes, plural) that has earned him a spot with the doctors. Ok, so during the date, he was super touchy. Had I been into him, that would’ve been a-okay with me…but I wasn’t, so I was a bit squirmish. When we left the bar, he said he would walk me to the subway (I figured I’d save a few dolla dolla bills after my pricey Uber ride over). Along the way, he had his arm completely around me, and since I didn’t want to have any sort of limbs wrapped around him, I instead ended up fussing with my purse throughout the entire walk.

dont put your arm around me

We were across the street from the subway station.  I could see it.  I was so close to getting out of this awkward situation.  But then… the Walk sign turned off, traffic started moving again, and I was stuck in his embrace at the crosswalk.  Next thing I know, his arm isn’t around me anymore and now he’s standing right in front of me.  I knew what was coming, and so I tried to look very busy searching the depths of my purse for my train pass.  Obviously this didn’t stop him.  He moved closer to me and planted a kiss right on me.

dementors kiss

Fortunately the forced kiss didn’t last THAT long because I was making sure to pay close attention to the street signs and traffic which allowed me to bolt once it was okay to cross the street.  Although his kiss was unwanted, I figured it would at least count towards any “thank you and goodbye” rituals that could potentially take place before parting ways.  Well, it turns out this was only the beginning.  This guy – who, as a reminder, lived walking distance from where we were – decided to join me underground and take the subway as well. He followed me through the entrance, led me onto the escalator (yes, he had his arm around me again and basically physically forced me to take the escalator instead of the stairs), and held me in place and was super touchy-feely the whole way down (yes, he was so smothering that I couldn’t walk down the moving stairs to speed up this escape process).  The time it took to go from the entrance to the actual gates where you pay was probably no more than a minute, but it felt like way longer.  All I wanted was to get rid of this guy.

shining you cant get rid of me

We buzzed our passes, he walked through, and for the first time ever I was pumped that my pre-paid card had run out of money. Mwahahaha we were now not only separated by a very reliable barrier, but in that same moment I realized that he was taking an outbound train and I was taking an inbound train.  YES.  I hollered to him to just go ahead and leave towards his side of the tracks, but he said he would wait.  UGH.  Ideally I would have taken my sweet ass time, maybe gotten my PIN code incorrect a few times just to prolong the precious moments I had away from him… but my train was literally about to pull into the station, so I had to move fast if I wanted to avoid a potentially longer wait with him in the event that I missed this train.  So I refilled my pass, went through the gates as my train was rolling in, and because I was practically running at this point, I did this sort of side-shuffle & goodbye-wave thing as I galloped away from him.  NOPE.  None of this stopped him from running up to me, grabbing my arm, and planting a kiss on me.  (Note: if I were into him, I could’ve equated that to a romantic scene when the guy chases after the girl on the train for one last kiss… but since I wasn’t into him, I’m letting the double standard exist.)

I turn again to rush towards my train because at this point I could actually see it slowing down for people to board.  But he’s still there behind me, also rushing towards the train.

Him: “WAIT!”
Me: “For what??”
*He grabs my arm again*
Me (as I continue to speed walk even faster towards the train, despite the fact that he is trying to slow me down): “Don’t you have to take the outbound train?!”
Him: “I want another kiss.”

I wish I was kidding.  He was seriously so aggressive.  I kissed him, shook him free, and was now about to break into a run because the train was at a complete stop at this point.  But he persisted.

dont go

Him: “Hold on!”
Me (now clearly expressing the annoyance in my voice): “MY TRAIN IS HERE.”
Him: “I know, it’s right there.”
Me (confused/wtf are you getting at): “EXACTLY.”
Him: “So you are fine.  One more kiss.”
Me: “No I need to get on this train.”
*He runs up to me and kisses me again.*

I didn’t even look back or acknowledge him after that last kiss.  I sprinted away and managed to make it on the train before the doors shut.  After all that, I had expected to hear from him again, but I never did – and I was not going to complain!  However, on my train ride home, the guy I had gone on a first date with that previous Thursday (the Adrien Grenier look-alike that I referenced in my last post) had texted me and asked me out on a second date.  I’ll be honest, I left date #1 feeling very mehhh but because he didn’t really exhibit any major dating problems, I figured I might go out with him again if he asked and if I had nothing better to do.  BUT by the time I received his text on this particular Monday evening, I was finding myself actually excited to accept his proposal for drinks near me because I at least knew that it would be 110% more enjoyable to spend time with him again than another guy like the subway stalker. So there’s my silver lining, I guess.

#Thursdate with Boston Girl & Boston Hater

Today’s #Thursdate is from one of my readers in Boston… and it’s pretty impressive. The date lasted only one drink, and this guy managed to pack in more problems than most guys display over the course of multiple dates.


The two connected through Coffee Meets Bagel. Although he seemed a bit pretentious based on some of his profile responses and his pictures were a bit blurry, they still scheduled a date to meet after work at a bar. And to properly set the scene, it was a decently nice bar in the Financial District where apparently pretty much everyone shows up in suits or at least some form of business casual clothing.

Problem #1: WTF Are You Wearing

Boston girl arrived at the bar, which was full of professionally dressed men and women.  A few minutes after she got situated, Boston Hater came waltzing in wearing baggy mesh shorts, a t-shirt, knee-high socks, basketball shoes, and disheveled hair.  It looked like he had just come from the gym or a re-creation of Aaron Carter’s “That’s How I Beat Shaq” video…but he hadn’t.  So either this guy is the perfect example of why Queer Eye for the Straight Guy needs to be back on the air, or he was planning to go workout right after the date = he has no patience or respect for his date.  All in all, things were headed downhill before they even greeted each other.

bball outfit

Problem #2: Kinda Catfish

Considering this guy’s profile pictures were blurry, I can only imagine how unenthused Boston Girl was to get a close-up of him after having the misfortune of seeing his outfit.  The good news is that he wasn’t horrible looking and that the fuzzy images he provided weren’t entirely different from how he looked in person.  Buuuut like most guys online, he lied on his height.  Boston Girl was in heels and based on the height he provided, that shouldn’t have been a problem.  So when they were finally face-to-face, he lost some major points for being barely eye-to-eye with her.

youre tall

Problem #3: Judge Judy

The two started talking the usual small talk, which of course includes “where are you from/where did you grow up?”  Boston Hater was from Philadelphia (now living in Boston), and Boston Girl was from Boston (born and raised).  This smooth talker really nailed it with the things he said next:

  • “Boston girls are the worst.  They think they are so hot.”
  • “Boston girls all think they are such hot shit.”
  • “If I’m at a bar, I am always trying to be a gentleman, but then I will see a Boston girl across the bar thinking she is all that.  So I just go up to girls like that and say, ‘you’re not as hot as you think you are’ and walk away.”

Really strange way to direct the conversation seeing as our gal literally just told him that she was, in fact, a Boston girl (not to mention, who the hell randomly goes up to girls and says something like that?!).  It was so bizarre that she interjected shortly after he started his rant and talked about how her family still lives in Boston, how she is still great friends with the girls she grew up with in Boston, how she went to school in Boston.  Basically, she wanted to make sure that he she made it clear that the defendant was in the shower she was from Boston and the group of people he was shitting on included the girl sitting next to him at the bar.  His response?  “Oh, well you’re not one of them.”  Ha, great recovery, dickhead.

shut up

Problem #4: Pompous

Unlike the depiction of his height in photos, the pretentiousness that shined through on his profile was actually a great indicator for what he was like in person.  After he rambled on and on about how he was better than every female in Massachusetts, the conversation shifted to online dating.  Boston Hater admitted that this was his first online date…but the only reason for that was because the Coffee Meets Bagel app was broken.  Wait, huh?  Yep, he explained how Boston Girl was the only match he had gotten so far, which obviously meant that the app wasn’t functioning correctly.  Earth to Matilda: it’s not the app.

nobody likes you

At that point, she had had enough of this delusional guy and said she had to go once she finished her first drink.  She told him “Good luck in Boston!” and expected (and hoped) to never hear from him again.  Funny thing is that he actually thought the date went well and he reached out for a second date.  NOPE.

Good news, though: Boston Girl did eventually find love through Coffee Meets Bagel!  She told me how she and her now-boyfriend were matched through the app and have been together for about a year 🙂  Cheers to love on the East Coast!