The Top 5 Worst Dates I’ve Ever Been On

Before I moved to Switzerland, before I found romance abroad, I was in New York City and dating was impossible.

I tend to attract very strange people, my dating life being no exception. If you know me at all, you know that I have been on some really horrific dates in my short, 23 years of life. I’ve decided to list the top 5 worst of the worst, the creme de la creme of bad dates. 

If you’re going to get anything out of this list, though, just remember -you have to sit awkwardly across a table from a lot of frogs before you can finally find your prince (or princess):

The FBI Interrogator  

It’s funny that I am now dating a native German speaker, because after this date I vowed to never date anyone German ever again.

I met up with this guy at a very cute bar on the Upper East Side on a Friday night and at first, things were going well. He was attractive, well dressed, and had an accent. However, as we sat down and got our drinks, things started going down hill real quick. Even though he was from Germany, his English was impeccable and he liked to make sure everyone in the entire bar knew just how impeccable. I can deal with a little bravado on a first date, but this was overkill. Before the bartender even brought me my first beer, this dude was rattling off questions in my direction.

“Where do you live?”

“How often do you come here?”

“What did you study?”

And so on and so on. He barely even let me ask him a question in return. I felt like I was getting investigated for murder.

After getting through asking me the trivial questions that I’m sure are mandatory for cops to ask when in an interrogation, he asked me what authors I like. In my head I was like “Finally, a question that feels personal!”

 I listed a few of my favorite authors but then fell silent and he looked at me and said “Keep going.” Was I being tested? Would I be graded on this later? What the hell was going on?

I tried stopping to ask him what kind of things he liked to read but he just said “No, I’d rather you keep listing.”

I was so uncomfortable. I didn’t know what to do with my hands. I was sweating. A nice evening had turned into a question of my intelligence, my existence. This man was like a walking Buzzfeed quiz generator. I expected him to have me list my favorite condiments in alphabetical order next.

After I finished my first beer, he ordered another round without even asking me and then he said he had to go to the bathroom. I didn’t want the other beer but this man had driven me to drink and I was sort of relieved that he was going somewhere else so I could catch my breath.

He got up, went to the bathroom, and I kid you not, never returned.

He just vanished into thin air and left me with a $50 tab because he had apparently had a few drinks before I arrived. Thankfully, the bartender had heard the entire encounter and offered to pick up his side of the tab, while throwing in a few shots and a whiskey ginger the size of my face for good measure. A bad night turned into a solidly drunken one but I flinched every time someone asked me a question for a few days afterwards.

The Snob

I met this guy at a party and thought he was pretty cute, so when he asked me out for drinks the next night I was absolutely down. I wish we had spoken more at the party, because then this date could have been avoided entirely. We met up in Williamsburg at a bar known for their craft cocktails. I should have known what kind of person this guy would be after he pointed to the chandelier in the bar and told me the history of it, but it was an interesting anecdote so I gave him a pass. We got two overpriced cocktails and sat across from each other, awkwardly shifting from side to side as we embarked on what would soon be an excruciating first date. We talked a little about the party, who we knew there, and things were flowing alright for a few moments. Then, I asked him where he went to school.

His answer made my eyes roll so far back into my head that they took a vacation.

“I went to this little school in Rhode Island. I don’t know if you’ve heard of it, maybe you have. Brown? University?”

I tried really hard not to let my jaw drop to the floor. Who did he think I was that I would be the kind of person who had never heard of an Ivy League school like Brown? Did he think that this morning, I had crawled from out under my rock in a backwoods swamp, stole some clothes from Forever 21, and came on this date? Of course I had heard of Brown f*cking University.

I tried to be polite because my cocktail wasn’t even halfway finished so I just nodded my head and sarcastically replied, “Yeah, I think I’ve heard of it.”

I kept noticing that every time he spoke his voice suddenly changed into this nasally, haughty tone and he would roll his eyes and touch his hair when he spoke. It was like he was trying to emote sophistication but instead came across like a complete and total douchebag. It reminded me of this old Family Guy episode, where they visit an Ivy League college and everyone speaks in ridiculously haughty voices while laughing like geese. That’s how he laughed.

Before the date ended (I kept hinting how tired I was so we wouldn’t get a second round), we moved on to talking about television. I love TV, so I hoped maybe this subject would redeem the date a little. Nope. It made it worse. The following were actual words that came out of his mouth. I can’t make this up people:

“I only listen to Kanye West and watch Mad Men. Everything else is for unintelligent people.”

I blinked at him, trying very hard not to start an all out debate with this mansplaining, ironic floral shirt wearing asshole, but instead I finished my drink and got out of there faster than you can say “Have you heard of it?”

The Drunk

Listen, I like going out as much as the next person, but when I go on a first date, I expect my date so be at least sober for the beginning of it. I met this guy, let’s call him Brian, on the Subway and we’d been texting on and off for ages. We both led very hectic lives so we never could find a time to schedule in a date. One Saturday, I was gearing up for a crazy night in with Netflix and Chinese takeout when Brian texted me and asked me what I was doing later. I lied and told him I wasn’t sure yet so he said, “Finally! Come have drinks with me!” I hadn’t been on a date in a while because I was just getting out of tumultuous “not relationship” with this Russian guy who had spent 6 months putting my heart through a meat grinder over and over. I closed my Seamless delivery window and decided to get all dolled up and give this guy a chance. After all, he seemed witty and smart and fun. What did I have to lose?

Brian picked one of my favorite bars in Bushwick so I had high hopes. I showed up, the bar was crowded, and he kissed me on the hand and told me I looked beautiful. He looked handsome and was taller than I remembered. I thought “This could be fun.”

However, as we found a seat in the corner so we could hear each other over the music, I noticed that Brian’s eyes kept closing a little and that his words were slurring. He hadn’t even taken a sip of his drink yet. We were talking and I slowly started to notice that this dude was completely smashed. It wasn’t even 6 pm yet. It was a Thursday. Didn’t this guy have a job?

He wasn’t a bad drunk but the fact that he was wasted at 6 pm was such a turn off. To make things worse, he kept trying to kiss my neck and his breath reeked of booze. I don’t care about kissing on the first date but this was literally only like…fifteen minutes in.

He kept trying to grab my hand, could not remember anything we spoke about just five seconds before, and one time he literally fell asleep for a few seconds. I woke him up and he kept apologizing, saying he isn’t usually like this, that he’s wanted to go on a date with me for a long time, blah, blah, blah. I was so turned off by this point there really was no redemption.

I thought of the Chinese food I had left behind and became severely annoyed. The bar was so crowded and I was trying to map my escape but thankfully, I didn’t have to find one. Apparently, he had forgotten that he was supposed to go to a party so our date was just a stop along the way on the path towards his blackout. He asked me if I wanted to come with him. I said no. He left shortly afterwards and I went to find my favorite taco truck.

I learned that night that Tacos are forever and drunk boys in bars are not.

The Tree Stump

Have you ever been on a date with the human form of a brick wall? Well, I have. I met this guy on Tinder or OKCupid or some sort of online dating site and he was hilarious. Every message he sent was filled with wit and bad puns and he literally had me laughing out loud the majority of the time. He seemed right up my alley and when it was finally time to meet up with him, I was ready for a night filled with stomach-holding, eyes-tearing laughter. What actually happened was….the complete opposite. I was supposed to meet up with my best friend Abby that night and the guy said he would love to tag along.

I had been talking about how funny he was so Abby was almost just as excited as I was to meet this guy. Abby and I waited in the bar when we see this very skinny, ghostly figure walking up to us. In his Tinder pictures, the guy actually looked like a living, breathing human being. What we got in person, however, was the undead version.

 The guy hugged Abby and I and then all three of us just stood there, blinking into our beers. Abby and I talked and the guy just stood there in silence. I started sweating a little. Where were the laughs? Was he just nervous? Maybe he had had an off day? We tried to initiate conversation with him and he obliged but everything he said was as exciting as receiving your electricity bill in the mail.

To make things worse, he kept playing some game on his phone in the middle of conversation. Abby, being Abby, was so bored and decided to suddenly have plans with her boyfriend. She left me alone with the most boring man alive (I still hate her for it).

I  did not want to spend one more moment alone with him because even though he spoke more when it was just him and I, there was not a funny bone in his body. I was so confused. Where was the stunning wit? The side splitting jokes? Where the hell was the guy I spoke to for hours the week before? I was frantic, trying to figure out a plan.

My friend Jessie (who is also a travel blogger) was texting me that she was at Barcade and to come with the ghost man.

“If I can’t get him to talk, no one will. Come!”

I decided to give this guy one last chance at redemption. Plus, maybe a change of scenery was exactly what we needed. After all, he liked arcade games, I liked drinking, what could possibly go wrong?

We got to Barcade and I was so happy to be around people who actually spoke in full sentences. Jessie and all of her friends made it their mission to get this guy to talk. Even Jessie’s Airbnb guest, a nice guy from Germany, was putting in his best efforts. Despite it all, the guy was just as boring as ever. His answers were like watching paint dry. I was at a loss.

Jessie and I started to talk about hair products, and the German Airbnb guest jokingly turned to the guy and said, “How about we have some shots while they talk about their girl stuff?” The guy literally said nothing. He just stared. Was he dead? Were we having a ghost encounter in the middle of Brooklyn?

The German guy was so confused by him and turned to me and whispered, “What are you doing with this…with this…Tree stump.” I laughed harder at that than I did anything Tree Stump had said all night.

The date finally came to an end and the guy became known as “Tree Stump” among my friends. When I got home that night, to make my confusion even more palpable, he texted me and said: Thanks for tonight! I had more fun than I’ve had in ages. Let’s do it again soon!!!

What? How did he have fun? When did he have fun? Did I turn my back and miss it? Was it when I went to the bathroom when he had this sudden burst of fun?

It was then that the living tree stump stumped me. Honestly, I’m still confused.

The Alien Enthusiast

When I was a bright eyed 18 year old who had just moved to New York City, I worked as a barista at Starbucks. Anyone who remembers me during those days can vouch that I was a very flirty barista. I would often put my number on attractive guys’ cups.

  In the beginning, there was a regular who came in often when I first started working there, and he was very cute. We had a minor flirtation but nothing more than that. One of my coworkers, Alberto, decided that he was going to play matchmaker. The daily conversation usually went something like this:

“Yo, Tess, I am going to give that guy your number.”

“No, you’re not.”

“I’m going to do it.”

“Don’t. Oh my god, please don’t.”

“I’m doing it.”

One day after work, I got a text from an unknown number saying that Alberto had given him my number. I could have killed him. The regular asked me if I wanted to go to dinner that night, and because I was hungry, I reluctantly said yes.

We went to a cute little mediterranean restaurant on St. Marks. The first red flag was when the guy ordered for me. Because I was 18 and not as outspoken as I am today, I let him. Thankfully, he ordered something I liked but I was still annoyed. Dinner went alright, he said a few things that were a bit odd but nothing that caused any bells to go off. So, when he asked me if I wanted to go get bubble tea afterwards, I said why not. This is when stuff got weird.

As we sat down with our bubble tea, the first thing he said was, “You know who you remind me of? My ex girlfriend that I hated but so much better.” Um, okay. Thank you? How is someone supposed to respond to that?

He had told me at dinner that he had quit his job and over bubble tea he decided to tell me why.

He moved closer to me, and closer, and closer until his mouth was right up to my ear. He took a huge breath. He smelled like hummus.

“I quit my job because I think I’ve found proof of alien life.”

He pulled away from me then, waiting to see my reaction, and my first thought was to laugh. However, his face was stone serious, his blue eyes stern and staring into my soul. I stopped laughing then.

He then told me that he had found these congealed stones in his backyard in Long Island and became convinced that they were alien eggs. Easter has just happened so my only thought was that they were, well, easter eggs. But I kept my mouth shut. He was so passionate about these aliens that it started getting a little scary. He kept talking about how the alien lord was going to come down on us and cause the apocalypse. (Maybe he was predicting a Donald Trump Presidency?)

I mean, I get it. I love X-Files and the truth is probably out there but I don’t think aliens are really the best topic to bring up on a first date. I texted Abby with an S.O.S and she called me pretending to be my mom. I got out of there as fast as I could.

The next morning, I woke up to 50 text messages from the guy with links to alien conspiracy sites. This was before you could block a number directly on iPhones so I had to go to AT&T and block his number. The worst part, though, is that he knew where I worked so he would come into the store while I was behind the register, sit at the table facing me, and would just stare at me without ordering anything. He did this everyday for two weeks until he finally creeped my manager out.

He went down as the weirdest person I’ve ever been on a date with. Ever.

Alberto still owes me a drink.