The Worst Date of My Life
Would testify under oath to everything below, it is not satire but my lord is it comedy!
It’s 6:45 pm on a wintry Sunday evening, the weather outside isn’t frightful but by no means is it delightful.
While checking my outfit, a notification from my phone shined bright from the bed. It is a text from the young woman that is supposed to meet me in less an hour. Anxiously thinking she is cancelling (I wish she had), she inquired about my arrival status to the venue. I informed her that I was about to call my Uber.
She asked if I can add her as a stop to pick her up in my Uber so she does not need to call one herself. Not the first time she asked me to call her an Uber as she did this on our first date too except she asked me to call her one for just herself that time.
Checking the surcharges and it being in the opposite direction of where we are going so the price more than doubled from $9 to $25 to add her as a stop. But, in my mind chivalry is not dead and our first date went so well I thought maybe this one is worth it. Maybe she is one of the three great women in my life like they say in A Bronx Tale? So fuck it, I agree and added her as a stop with no qualms.
Now, I am someone who does use the devil’s lettuce recreationally but, I avoid using this before dates. Upon my arrival at her apartment complex you could smell the bong rip before she even leaned in for a hug as she got into the Uber.
After holding my breath for the Uber ride where I listened to this person talk in what was a stoned, slow motion Long Island accent, we arrive at the venue in downtown Boston. She asked me to get us drinks before we go to the back room for our seats to which I obliged.
To paint a picture, this comedy show is at most twenty people in the back room of a dive bar. With that visual just imagine during the first two acts (who only have about 10 minutes each), someone constantly pulling you in to talk during their performance. That was my date. The only reason this paused was by the third performer getting on stage she had asked me to buy her another drink.
As much as I did not want to miss this upcoming set, I needed to breathe for a minute. As soon as I stepped out of the room the hot flashes from being perturbed subsided.
Slowly, I sipped my new beer and carried her vodka soda back in only to be told how funny of a comic I just missed in the last few minutes. He finished his set and the next two comics go on with some jokes that were albeit, out-there but by no means off limits for jokes at a comedy show - mind you a 20 person bar room comedy show.
Her face was filled with disgust at these two white, Jewish comics who joked about the border and other topics she thought were “off limits” for them. I brushed off her comments and tried to enjoy the rest of the show despite getting commentary on almost every joke in the last two sets.
The show ends and as planned I entertained the idea of us going to grab a bite and maybe one or two drinks at a nearby restaurant - a 5 minute walk. After showing her the maps she balked at the idea of walking proclaiming “that’s too far I hate the cold, call us an Uber to Publico”. It was roughly a 15-20 minute drive from where we were in downtown Boston.
The steam had not yet begun piping out of my ears mostly cause she is rather attractive and I’ll admit it became purely lust not love at this point. BUT, I should have followed my instincts and called it a night upon the unwillingness to walk 5 minutes.
Our next Uber ride was almost more painful than the first. For starters - she kept touching my legs/my face and maybe it’s my “touch of the tisms” or just things I would not do to someone else on a SECOND DATE in an Uber but it annoyed the ever living shit out of me. Like snuggle in an Uber maybe, but if the roles were reversed & I did what she was doing I’d probably be considered a fucking creep.
After informing her of my Zodiac sign there was what felt like an eternal interrogation into “how can you be a Scorpio you don’t give those vibes at all?”. After shrugging my shoulders about five times more than I wanted to we arrived to an empty restaurant (thank Baby Jesus because no one is ready for what’s about to ensue).
Upon the host seating us at a booth she asked me if we can sit on the same side. I don’t know why I tossed my spine out the window of the Uber and agreed to that because it was simply the worst. She began after our first round of drinks saying “those short, white, Jewish comics should not have made jokes about the border and other non white races - it’s just not their place”.
This is where I officially lost my patience because to me, a comedy show is where any joke is fine by me & the audience will tell you whether or not it was funny. Also, once she brought their race/religion into she became worse than their jokes in my opinion. So I decided it was time to gaslight. And by gaslight, I may as well have tossed a Molotov cocktail in her face.
Me: “Yeah I hate when Middle Eastern, Latino and other nonwhite races use the N-word.”
She is Persian so I knew this comment would strike a nerve (not my long-term ex…just have ended up going on dates with a few Middle Eastern women following that relationship ending).
Her response “Middle-Eastern people simply do not do that”. (Never seen someone so confident in being wrong)
Me: “Oh yeah, well once I was leaving a bar and this guy kept saying it at me over and over because he thought he could be a tough guy and kept saying ‘my nigga’ to end every sentence so I challenged his privilege and said ‘you have about as much a right to say that as I would to say shit about Gaza right now”.
She was aghast, disgusted, and by this point about 3 drinks deep and minimal food; considering her petite frame she definitely was buzzed if not drunk. She erupted in tears and began yelling at me saying “how could you say that!? You are worse than him and I have family over there”.
Clearly not understanding my point of trying to tell this person he just should not try to call me “nigga” just cause he and I are both brown as that word is not for his people just as I do not have a right to talk about Gaza. It did not matter as she fully erupted over and over yelling and causing a scene in the restaurant.
Wanting to just go home I said “how about I get the check, we cut ties and call this a night because clearly there is no more future here” to which she agreed. I asked if she wanted the leftovers to which she said “no you can have them”.
I went to the bathroom and came back out to both her and the food gone. I stepped outside and began to light a Ben Affleck meme level cigarette for the walk home. As I raise the lighter my internal monologue took over exclaiming “what a shitty night with an even shittier person”.
As my head turns I see her dart from behind this post to get into a Lyft, but before she gets off the sidewalk she takes the leftovers and places them on the ground. I waved goodbye to which she did not even acknowledge my existence. I picked the food up off the ground in its box and placed it in a nearby trash can to not litter. Continuing a lonesome walk with headphones in a I sent an apologetic text for the way that story riled her up. She responded by calling me a dog and to eat scraps off the ground. She unsent a rather scathing message but alas you’ll find the damage below the rest of this story.
Getting further annoyed at how she is blowing up my phone I walk into a bar to have a cool down beer to get my mind off it. Once I leave I check my phone to find a multitude of messages on my phone. I arrive home and tell my roommate the story and low and behold one of her messages is asking if I still wanted to “hang out” which in the dating world usually means hook up. I was shocked and decided to just play along. Honestly fuck it, you’ve gotten the gist of this long ass, terrible date here are the screenshots of the rest of it below.





