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.


#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!

The Attractive Pompous Douchebag

This next guy is pretty amusing.  I started talking to him through OKCupid at the beginning of March.  We originally made plans to meet up on a Wednesday at 8:30 at a local dive bar that I had never heard of before.  However, Wednesday morning I asked him if he would be okay with rescheduling for a day when he could meet up earlier because it was a long week and 8:30 would be cutting it with my bedtime (and I apologized for being such a grandma).  He said it was no problem, so we planned for the following Wednesday.

The following Wednesday rolls around, and he texts me: “How about 8:30 tonight at the same bar we planned for last week?”  Ummm… did you not get the memo about why we rescheduled for a week later?  Whatever, I wasn’t as tired that day, so I agreed to the plan.

Problem #1: Inconvenience

So first of all, there was no convenient means of getting to this bar via public transportation, and the routes that were available would have taken roughly an hour for me to get to this little dive bar.  So I called an Uber, and the total round trip ended up being about $30.  That price is not too horrible, but considering how much money I dropped that night (I’ll get to that), it was a bit much for a first date (but in his defense, I could have requested that we meet somewhere else…and I probably don’t get sympathy points from any guys since they usually end up footing the entire bill on EVERY first date).  Anyways, he had texted me shortly after 8:00 saying he was going to be a little late, and so I didn’t feel too bad arriving a few minutes late as well.  I walk in, and this bar is TINY.  There was also a live band, and so it was VERY loud.  Although I wasn’t entirely sure what he looked like (see Problem #2), I knew he had not entered the bar yet.  How did I know for sure?  Well, because every single solitary human being in this bar was over the age of 40.  I thought I was being punk’d.  I sat down at the bar and ordered a beer on my tab.  5 minutes later, 10 minutes later, 15 minutes later, and still no sign of him and still no text.  After waiting 20 minutes and almost finishing my beer, I was ready to just leave…but then he showed up.  No apology for being late; he just said he had to take the trash out (even though he has 4 other roommates who could have done it instead).  Cool, I’m glad to know that I fall below trash on your list of priorities.

pointless waiting for you

Problem #2: Kinda Catfish

Like I mentioned, I wasn’t entirely sure what he looked like because some pictures showed him with light buzzed hair and others showed him with a bit longer brown hair.  Going into the night, I was fine with either option (turns out he was the light buzzed hair version of himself).  But once he Facebook friended me the next day, I realized that his brown haired photos dated all the way back to 2006.  I get it if you use a photo from 1, 2, or even 3 years ago, but nobody should be portraying themselves to be the person they were 8 years ago.  It’s just deceiving and annoying.

how old were you

Problem #3: Pompous

Even before meeting, I had a feeling that this guy was super pompous just from a number of things he said in his profile.  Turns out it was a great reflection of what he is like in person.  Never have I ever met someone (I’m talking anyone – not just people I’ve met on dates) who thinks they are so far above everyone else.  I’ll just list out a few specific things that made me want to punch him in the face:

1) He refused to tell me his name.
Yep. Going into the date, I did not know his name because he refused to tell me.  When he continued to refuse to tell me at the bar, I called him out for being super sketchy.  He responded by saying that trivial questions like that would provide no important information to help me better understand who he is as a person.

2) He is just way too good for anything mainstream.
Why were we at a tiny bar full of 40-year-olds?  Because he is above going to the popular bars.  Why does he have a dumb phone?  Because the iPhone is unnecessary and he is oh so resourceful without needing the pointless extra technology.

3) He questioned basically every single thing I would say.
Basically any time I would say something, he would squint his eyes, zero in on me, and rub his chin with his thumb and index finger as if deep in thought.  Then he would say, “I wonder why you would say that.”  Honestly, I can’t remember specifically what things I would say that warranted that response, but I do know that he did this at least half a dozen times throughout the date.

chin thinking

Problem #4: First Date Check

After we finished our third beers, I decided it was time to go.  So I ordered an Uber and told my date that I was going to close out my tab.  He didn’t offer to cover it for me, but at that point I was so bothered by him that I didn’t even care.  We hugged goodbye, and I hopped in the Uber.  A few minutes later, he texted me asking if I paid for his drinks.  No wonder the check was $50!  I guess the bartender must have just put his drinks on my tab.  Easy mistake, and I suppose I can’t blame that on my date.  What pissed me off though was the fact that he never once said thank you.  Not over text.  Not in person.  Never.


Hahaha sooooo… you would think that I would never want to see this guy again, right?  Well, I definitely wanted to punch him in the face, but I also wanted to make out with him.  WTF?!  Yeah, it makes absolutely no sense.  But being picky, it’s pretty rare when I meet someone who I am actually very attracted to.  Sucked that his personality was so incompatible with mine, buuuuuut I was open to a second meet up just for the purpose of making out with him (but not more than that…he wasn’t THAT attractive).

that makes no sense

So stay tuned.  It only gets better from here.