#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!


One Drink Wonder

Somehow, most dates I go on end up being at least two hours where I have at least three drinks. This next date – also from Coffee Meets Bagel – lasted less than an hour, and we only had one drink (thankfully). Here are the major reasons why:

Problem #1: Chronic Swearer
I will be the first to admit that I swear; most people do. But when you have the mouth of a sailor in public with a total stranger that you should be trying to impress, it is not attractive. This guy was dropping F-bombs left and right. He also was not a quiet guy, so I wasn’t even the only person who had to endure the string of curse words that he was just rolling off.

chronic swearer

Problem #2: Juan Pablo Syndrome
No explanation necessary. Classic case of the guy who loves to hear himself talk about how awesome he thinks he is.

helga dos equis

Problem #3: Judge Judy
It sounds hypocritical for me to say I don’t like guys who judge people when I have a blog dedicated to doing just that. But I’m not on a date with you right now. While we were having our one drink, this guy made a comment about how he thought our bartender was overweight (she wasn’t), how the woman on TV’s boobs were showing too much (he was kind of right…but stop looking at her boobs), and he even had the nerve to criticize what I was drinking. He wasn’t poking fun at it; he was straight up judging Regina George-style. Whatever, I just didn’t let him buy me another drink. I said I had to catch the T and peaced out.

judge judy

To date, this is the only date I went on and didn’t even attempt to offer to pay.

Anesthesiologist: Round Two

After a somewhat successful first date with the anesthesiologist, I agreed to go out with him again about a week later.  Of course, he obviously was not too bad because you will not see me being okay with meeting up with someone that I am not at least intrigued by.  However, this time around, I began to notice a few more areas where he was less than perfect.

Problem #3: Dull
Being an anesthesiologist, the conversation about his career was interesting on the first date.  It became much less interesting on the second date.  I quickly learned that with the exception of his job, he really did not have much going on.  Aside from the times that his Total Bro-ness was obnoxiously over the top, I was pretty bored and unamused.

dull and bored

Problem #4: Bad Kisser
The first goodbye kiss is always awkward to some degree.  It is even more awkward when only one person actually wants to kiss the other.  This is the situation I found myself in at the end of this second date.  It’s not like I had a miserable time (any date with food involved is always at least a little enjoyable), but I was just not feeling the vibe.  I wasn’t into it, and I had zero desire to kiss him.  But he wanted to kiss me, and I knew it.  I awkwardly tried to avoid it by sidestepping into a hug, but he got his hands on my hips and went for it.  What made it so bad?  Well, start by putting your lips on the back of your hand.  Now without taking your lips off of your hand, say the word “HOW” three times very fast.  That was how he kissed.

bad kisser

And with that, I finished my final date with the anesthesiologist.