My Worst Dates Ever Series, Part 1: The Crazy Pill-Popping Laugher

I’ll cut to the chase here: we’ve all had bad dates, but mine are sometimes outrageously insane. I still don’t know if it’s that I attract absolute psychopaths or if I am the psychopath; it’s up for debate. 

Do I feel bad writing about these guys? Yes, because some of them can’t help that they are extremely weird. In the interest of protecting the innocent (no one did anything truly horrible, unless you consider talking about dressing up at anime conventions “truly horrible”) I won’t use anyone’s name or list identifying details. Duh. First rule of karma.

First up: the pill-popper with the crazy laugh. You’ll understand why I call him that as the story continues; right now, all that is important is knowing he tricked me into thinking he was normal by looking REALLY good in his Vineyard Vines button down, boat shoes, and an awesome-fitting pair of beat-up jeans. I imagined, when I spotted him at the bar, that the jeans got worn-in while this guy was pulling his lobster traps up…see below and tell me that if you were a 22-year-old girl living in Boston, you wouldn’t be attracted to someone in this outfit?! My thinking was so warped! 


In retrospect, I should have known this guy was a weirdo. He had NO friends around him…was just chilling by himself on a Friday night, downing Bud Light after Bud Light ALONE! But I was so blinded by his preppy threads I could not see that “no friends” was probably a gigantic RED FLAG! 


We started talking, and he contributed to my personal food pyramid by buying me three or four vodka sodas. At this time in my life, vodka sodas took the place of the “grain” category (vodka is a grain, after all) on the bottom, and the rest of the pyramid consisted primarily of frozen yogurt, coffee, cupcakes, and Domino’s pizza. 

We chatted for hours–he was from a beautiful part of southern Massachusetts and seemed to have a close relationship with his family, which is always nice to hear. He talked about going home to be there for his sister’s prom, for God’s sake! How cute was this guy?! 

Next came the requisite “What do you?” part of the conversation. He was in some boring finance job, but what else is new? The only options for guys in Boston are finance, medicine, or Dunkin Donuts franchise owner. Sadly, I have not met the latter. THAT would be my dream man. 

Pleased I had met a seemingly decent guy, I gave him my phone number. He called me the next day (yes, CALLED…) which I took as a sign of unparalleled maturity. In this age of texting, getting an actual phone call made me feel like this: 


He told me he would pick me up for dinner the next night. I was excited–woohoo, a dinner date!! AND I was getting picked up…in a car! Considering most people around my age don’t own cars in the city, knowing I would get to ride to a restaurant in a car made me feel like this: 


So far, so good! 

Appointed pick-up time was 8 pm, so naturally I was ready by 7:30, but planned on pretending to be ready by 8:07. Unfortunately, Crazy thwarted this plan by NOT showing up at 8 pm. Anyone who has had this happen to them understands the feelings involved: you start out sitting there watching a rerun of Friends, and before long your sweaty hands have pushed an entire bag of Tostitos into your mouth out of panic. 

Finally, at 8:14 pm, he called to tell me was outside. He apologized for being late; apparently, he’d had some work meeting in Cambridge. Mmmhmmm…WHATEVER! 

I went downstairs where my chariot awaited. Apparently, his “chariot” was his mom’s navy blue Volvo station wagon. No, literally…it was his mom’s. This 25-year-old man had borrowed his mother’s car for a date. Her reusable shopping bags were still in the back, along with directions to her gynecologist’s office, which were on the front seat. I had to move them to sit down. 

Okay, whatever…that’s fine…everyone has their “thing.” Maybe this is just another example of being “close to his family”????  

We began driving. And driving. And driving. Finally, I decided to ask where we were going. 

“Oh, well, I just moved here! You tell me!” 

Wait. WHAT??? 

So, this guy had just been circling Boston aimlessly for ten minutes, waiting for me to direct him to someplace that sold food. I’m not sure how long we would’ve been driving if I hadn’t spoken up. 

This is where things got tricky. As any girl knows, having a guy ask you “where you want to go” on a date, especially a first date, is risky territory. You don’t want to suggest someplace too expensive, because then you’ll look like a high-maintenance, gold-digging snob. Then again, if you pick someplace like McDonald’s, the guy might think you don’t know anything and consider you unsophisticated. What to do, what to do! I blurted out the only middle-of-the-road place I could think of, Parish Cafe. It’s actually one of my favorite restaurants in Boston and has an AWESOME selection of sandwiches and beer. 

Off we went. As soon as we sat down, I regretted the choice. This place has MASSIVE sandwiches. As in, you’re going to get kinda messy. And the last thing you want to do on a FIRST DATE is stuff your face with a sandwich that has a height of your entire face. I decided to order a salad. UGH. What a waste! 

Jealously I watched as Crazy ordered one of the most delicious things on the menu, the Zuni Roll. Here is the description from the restaurant. Try not to get drool on your keyboard! 

“Smoked turkey breast, crisp bacon, chopped scallions, dill Havarti cheese and cranberry-chipotle sauce wrapped in a flour tortilla and served warm. Sided with choice of homemade potato salad or coleslaw and a cranberry-chipotle sour cream sauce with scallions.”

Yeah, sooo…you can see why I was jealous!!! 

Anyway, the conversation started up normally. Where did you go to school? What did you major in? Blah, blah, blah. All I could think of was how much I wanted his delicious sandwich, until he said something about the town he was from. 

“Oh, I know someone from there!! Do you know _____?” (Name omitted because I dated him too. Hehehehe.)

“Yeah…umm…well, we were in the same grade, but then I left to go to boarding school.” 

“Oh!” I said cheerfully. “Which one?” Lots of my friends went to boarding schools and I love the name game. (PS, are you vomming yet over all this boarding school, East Coast preppy talk?! It’s sooo obnoxious, I know!) 

“Um, you probably don’t know it.”

“Oh, come on, tell me!!” I really wanted to know. Sometimes I need to learn when to shut my mouth, because this is when the floodgates opened. 

“Well, it was ______ School, because I had a serious drug problem in high school, and then I needed rehab, so I went there, and then I ended up stealing a bunch of stuff from kids at the boarding school, so I got kicked out and had to go to another boarding school.” He said this all as if I should not be shocked. Luckily, I’m a good actress. 

“Oh, wow, okay. Well, did you like your new school?” (My questions…hahahahaha…)

“Yeah, but that’s around the time I got diagnosed with several mental diseases. So now I’m on ______, ______, ______, and _______ to control my visions, psychosis and rage!” He let out a great big scary laugh. Like the Joker. I should mention he was about three beers in at this point. I was about halfway done with my first. 

At this point, I was terrified. Rage problems?! Psychosis?! Alcoholism?! Why was he drinking!? And wait…he DROVE me there! OMG!!!! How was I going to get home?! 

Despite this, I was sort of fascinated. I wanted to know more. I’m a sick, sick person. 

“So like, how did they diagnose you with all that stuff? Did you have to spend time in the hospital?”

“Oh yeah, it was crazy!!!” He started laughing uncontrollably. WTF was with this guy? He went on to tell me in great detail that because of his crimes and mental problems, he no longer has any friends from childhood or high school, but that’s okay, because, he said with another gigantic, crazed laugh and smile, “I make friends so easily! Like in boarding school, when I stole all that stuff from other kids, like money and stuff, I was friends with those guys! I was like, ‘Guys, it’s a joke, it’s not a big deal, come on guys!’ I’m sure one of these days they’ll come around!” 


I actually kept talking to him. I did not end the date. Again, I said, I am a sick human being. I was interested in how a person becomes like this. I wanted to know more. 

“Yeah, so like, what kind of sexual stuff are you into? In therapy, sometimes I talk about this with my therapist, and he says I should be really open and not be ashamed of like, my arrests, and other personal things. It’s just part of the healing process!!!!!!!” Crazy smile. Gigantic laugh. AGAIN!!! 

Thankfully he had stopped drinking, but he was on a roll in the talking department. I explained as we left the restaurant that I could just take a cab home, it wasn’t a big deal (translation: I am not getting in your car you drunk weirdo!) at which point he produced, I am not kidding, a breathalyzer. In his glove compartment. He blew under the legal limit. I let him drive me home. Tsk. Tsk. He may not have been drunk, but a breathalyzer cannot detect crazy!

I don’t remember much about the ride home except for the part where we stopped at a stoplight. It was red for a long, long time, and he was convinced, he told me, that aliens were controlling the stop lights and wouldn’t change it to green until they “felt like it.” 

You can’t make this stuff up. 

As I got out of the car at my apartment, he leaned in for the kill. And literally, it was basically a kill. I did NOT want to kiss this guy, but he had other plans. In the process of trying to make out with me, he broke my necklace! 

I ran out of the car. I never heard from him again. And I have NO idea what happened to this guy. 

Probably a good thing…





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