Serial Dating in Cuffing Season

It might just be coincidence, but I’m beginning to notice a pattern where my interest level in dating seems to change with the seasons.  Just around the time when the weather was becoming somewhat tolerable, I stopped dating.   Now that the weather is getting shitty out, I’m not only dating again…but I’m dating a lot.  Apparently this is “cuffing season” and apparently I am giving into it. Within the last two weeks, I’ve been on six dates:

  1. 10/16 – Date with the Hinge guy who looks like Adrian Grenier
  2. 10/20 – Date with the touchy guy who chased me into the subway for a kiss
  3. 10/21 (5:30pm) – Date with the moccasin-wearing admirer of sidewalks
  4. 10/21 (6:45pm) – Date with the pickiest eater alive
  5. 10/22 – Second date with the Hinge guy
  6. TONIGHT – Third date (!!!!) with the Adrian Grenier doppelgänger

Expect some upcoming posts about each of these guys… with the exception of the one I’m still dating because obvi he hasn’t had too many dating issues since I’m still agreeing to go out with him (and because it would kind of suck if I started to actually really like him and then he found a judgmental post I’d written about him for all of the internet world to see).  But hey, tonight could end up being a total disaster, in which case, there will absolutely be a post up about him in the near future!  Oh this dating thing sure can be fun…. evil laugh


Forgettable Dates with Unforgettable Problems

The month of September brought three new guys and three new dates.  Like California Rolls and unseasoned grilled chicken, none of them were bad, but none of them were especially good.  They were just very…. mehhh.  Since no one exhibited enough problems to deserve their own post, I thought they should at least receive honorable mentions here.

Date #1: The IT Guy
Dating Problems: Dull and Work Obsessed

Funny enough, I had been talking to this guy way earlier in the year.  We had even gotten to the point where we took it offline from OKCupid and were texting.  Then one day, I woke up and decided, “I think I’ll go to law school today I seriously don’t want to go on any dates anymore.” So I stopped talking to him. Legit just straight up ignored the poor guy. Fast forward about half a year and I’m all of the sudden messaging him again to hang out. For some reason he was completely okay with the fact that I was “really bad at texting” – ha, yes, that was my excuse to him – and we decided to meet up. I can’t really say many bad things about the guy because he was very genuine, he picked me up and drove me home, took me to an AWESOME restaurant, and had scruff. However, he was in IT. Now, let’s be clear: that in of itself isn’t a bad thing. It’s actually pretty awesome. But let’s also be clear: I don’t consider data centers, SOA, firewalls, or JavaScript to be interesting conversation topics. In fact, none of these topics are even in the realm of being considered conversational to me since I have absolutely nothing to contribute except for the fact that I’ve heard of these terms at one point or another in my job. Soooo that’s exactly what happened: I didn’t contribute anything to the conversation. Look, it’s great that he knows so much about his field, but I’m already not a fan of talking about work outside of work…and I’m especially not too keen about listening to the technical aspects of things that make zero sense to me.

boring me to death

Thankfully, he did eventually ask me about myself as well (thus, preventing me from diagnosing him with the Juan Pablo Syndrome).  Unfortunately, he later began talking about World of Warcraft which pretty much solidified my lack of interest in him.  Game over.

Date #2: The Mover
Dating Problem: WTF Are You Wearing

I’d like to give myself a pat on the back because it turns out I haven’t completely lost all ability to pick up a guy in person. The only thing that really confuses me with this particular situation is that I barely spoke to this guy and, in my mind, I was super awkward in practically every interaction I had with him. Whatever, to provide some context: at the beginning of September my roommates and I were moving closer to the center of the city and obvi had to hire movers for the heavy lifting. One of my coworkers had recently moved to the same neighborhood and recommended the moving company that she used (and also just so happened to mention that the crew they sent was full of good looking people), so I quickly gave them a call and snatched up one of the earlier timeslots for moving that day. I have to say, even if they were completely unfortunate looking, I would absolutely recommend them to anyone because they were amazing. Buuuuut it also just so happened that most of them WERE good looking. In particular, there was one very tall gentleman that looked fantastically masculine as he lifted heavy things and put them back down.

huge biceps kiss me

Like I said, though, I was being pretty awky, and I swear to you that I could count on one hand the number of times I spoke directly to him. Nevertheless, I was fully prepared to give him my number before he left because a) he was hot and b) I needed practice making moves on guys in person since my game has seriously struggled since online dating has become my primary means of meeting new people. Unfortunately, in true awkward turtle form, I failed to give him my number, and soon each of the strong men were out the door. HOWEVER, later that day about two hours after the movers had left, I got a phone call from an unknown number. I rarely answer for unknown numbers, but for some reason I felt like it was going to be him. Not kidding at all, I had some strange woman’s intuition moment where I had this intensely strong sense that the call I was receiving was from him. And sure enough, my intuition did not fail me; it was the mover, and before I knew it, he had asked to take me out for dinner later that week.

awkward surprise

Fast forward a few days and we were set to meet up a few minutes from my new place. He kept pushing back the time when we were supposed to meet up, which was extremely annoying because we were supposed to be getting dinner and waiting until 7…and then 8…and then 9 to eat a real meal was beginning to bring out the hangry version of myself. Typically I would just ask to reschedule but by this point I was three large glasses of wine deep with my roommates and the restaurant was down the block from me, so when he was finally ready to meet up, I buzzed out the door to meet up with my tall mover.

thank you alcohol

I figured it wouldn’t be hard to spot him since he was SO tall, and sure enough he stood out like a sore thumb.  But it wasn’t just his height that made him stand out: he was wearing one of those collared soccer jerseys with massive lettering and obnoxious patterns all over it.  Something almost identical to this:

croatia polo jersey

psycho shower screaming

Now that my eyes were blinded by the sight of this horrendous shirt that should never be worn at any time except during the World Cup, I just wanted to feast my eyes on food and some more alcohol.  Thank goodness the food was good and that I already had a pretty good base level of drunkenness from the vino because my interest level in him continued to go downhill.  It turns out he was two years younger than me, had dropped out of high school, aaaand… well that was enough for me to rule him out entirely.  We finished up at the restaurant, he walked me home, planted a goodbye kiss on me (good kisser, I’ll give him that), and then the next time he texted me was on a Friday at 1am.

Date #3: The Hot Army Guy
Dating Problem: He Didn’t Like Me

Ok, so I don’t actually consider this to be HIS problem. The truth is, this guy from Hinge didn’t really have any dating problems. He was interesting, funny, and resembled Channing Tatum after I was a few beers deep.  Throughout the date (and even now in hindsight), I really did think it went well… with the exception that my hair got a biiiiit on the frizzy side on my walk to meet him.

crazy hair

Despite the hair, I thought it was a shoe-in for a second date.  I mean, we had good conversation and he was in no rush to leave the bar – he was actually the one who wanted to keep getting more drinks (and he was paying for everything).  As I play it back, I’m thinking it may have been a good idea to not accept that last drink.  Why?  Well, I was exhausted since it was getting late + I already felt pretty buzzed before that final beer = a recipe for drunken exhaustion in its greatest form.

screaming fall asleep

I’m imagining it had to have been something dramatic like that.  Because let’s be real.  There’s no other explanation for why he wouldn’t want to go on a second date with me.  EVERYBODY likes me.

everybody like mes

Ok, no, I’m only kind of kidding and just trying to make myself feel better by using too many GIFs while simultaneously refusing to bruise my ego and accept that I may have been the problematic dater this time around.  Or, hey, it could have simply been that he just didn’t feel any sparks, which I can’t blame him since I feel that same lack of emotion for just about every guy I go out on a date with.  So yeah, let’s go with that: he just wasn’t that into me. (On that note, he even said something straight out of He’s Just Not That Into You when we said goodbye: “I’m going to be out of town for the next week, and it will probably be difficult to get in touch with me.”) Needtheless to say, he never reached out to me.  I eventually made two attempts, both of which were answered with silence.  So I gave up on that, and even though it was a bummer, it’s nothing that I got hung up on.  If anything, it gave me hope that I am still capable of being attracted to my potential suitors and that I’m not asexual.  Let’s just put a positive spin on it and call this a WIN.


Doctors & Kissing (A Public Service Announcement)

Get excited…because I am back in the online dating game!  After taking a break from dating in general, recycling someone who turned out to be the exact same as he was two years ago, and finally getting closure from my last relationship, the Picky Dater is once again meeting up with complete randos with a myriad of imperfections.

First up: the 30-year-old doctor. We started talking via OKCupid and he got major points for claiming to speak French fluently, for being well traveled, and for being tall. The whole doctor thing was cool too, but I’ll be honest, I keep finding more and more that I’m probably not the most compatible with the MDs. His scruff based on his photos was questionable, but I was willing to give him the benefit of the doubt because he was Canadian.

Our first date was at a creperie. He clearly didn’t do enough research on the place because it was supposed to close literally ten minutes after we got there. BUT Mr. Quebec saved the day, spoke French to the owner, and they kept the kitchen open for us. Our second date was at a swanky speakeasy-type bar, but we met first near his apartment. I was a little turned off by the fact that he had me come up to his place before we walked to the bar, but his profile said he had a dog so I was willing to be momentarily ignorant to the fact that he could easily be Buffalo Bill’s copycat (and no, I’m obviously not referring to the football team). Both dates were decent. The crepes were delicious, the bar served some really interesting concoctions, and he was overall a good and interesting guy. However, the sparks just were never there for me. Not sure if the following problems played a factor in that, but I’ll let you make that judgement.

Problem #1: Kinda Catfish

First off, let me just say that I was lured under false pretenses into the apartment of a guy whose profession is cutting open the bodies of human beings. HE DIDN’T HAVE A DOG. I asked him why he listed that in his profile and even mentioned it on our first date, and he responded, “I do have a dog; she lives with my parents in Quebec.” Ok, maybe I’ll just add to my profile that I have a boat…but it’s owned by my second cousin’s ex boyfriend.

Also, it wasn’t just the dog. While his photos were not a completely inaccurate depiction of what he looked like, they were definitely taken a few years ago because he looked a lot younger in those photos. I’m not saying that this guy looked like a grandpa, but he looked a LOT more aged than any other 30-year-old I know, so it would have been nice to have had my expectations set correctly before meeting him. But whatever, I honestly had a bigger problem with the lie about the dog.

you liar

Problem #2: Speak Up!

It was really difficult to hear this guy.  I come from an Italian family where everyone is screaming, so this has never been something I’ve been good at dealing with.  While I’m willing to take some responsibility for this because I know my hearing isn’t perfect, I still cannot find a justification for why I had such a problem hearing him in the creperie where zero music was playing. Also, he did this thing that at first reminded me of the pompous douchebag: almost every time that I spoke, he would zero in on me, lean in, and squint his eyes at me as if deep in thought.  I originally would have listed that look as its own type of problem, but then I was told that sometimes people squint their eyes when THEY can’t hear someone very well.  If you ask any of my friends, I’m sure they would agree that it probably wasn’t so much a problem with my volume as it was his ability to hear.  Don’t worry, I cut this guy some slack and this wasn’t really a huge deal for me… but being picky, obviously I took note of it.

staring squinting

Problem #3: Bad Kisser

After our second date ended, he kissed me.  And it was bad.  It was like kissing a snake: his lips were pursed really tight but then he suddenly surprised me by quickly trying to slip some tongue in there…but then it was back in his sealed shut mouth before I could properly figure out how to adapt to this odd style of a prolonged goodbye kiss.

snake tongue

It was worse than when the anesthesiologist kissed me.  Which brings me to this: why is it that the doctors I keep kissing just don’t know how to kiss?  I know this brings me to a grand total of only two doctors that I’ve kissed, but since they were both bad and I also have a friend who shared the same displeasure of locking lips with a kissing-challenged doctor, I’m considering this a trend that needs some serious attention.  It’s genuinely concerning to me that these types of people spend hundreds of thousands of dollars on school and countless hours in residency only to suddenly be three decades into your life without the knowledge of how to give a gal a proper kiss.  I do have to commend both doctors for even going in for the kiss, since I’m sure that’s half the battle.  So let’s raise awareness for this cause and help prevent these bright men from losing out on a next kiss, a next date, getting laid, or whatever it may be that they were hoping to get after what should be a magical moment.

prayer circle


All in all, though, it wasn’t the kiss that killed it.  There just wasn’t any any chemistry there – both before and after he snake-attacked me.  He asked me out again, but I had to be honest and told him something was missing.