8 Crazy Things I Did In New York That Beat Any Sex And The City Episode (And Are Probably Illegal)

Got my first tattoo on a second date, followed by a surprise “striptease” at the tattoo parlor.

Getting a tattoo on any date seems like a bizarre idea – but it’s not what you think. At the time, I had been in the early stages of dating a few different men and the man I was planning to bring along with me to get the tattoo started becoming a tad jealous and controlling. So, I had replaced him with another option from my roster that night – let’s call him Chad. Chad was a cute 6’3 software engineer from Texas who also doubled as a comedian in his spare time. We were at a jazz club sipping on cocktails when I mentioned the idea – I already had a tattoo in mind (and no, the themes of said tattoo did not involve any of the guys I was seeing). We started looking up tattoo places nearby (which were actually in abundance given we were in the West Village) and left the jazz club shortly after finding one that had a high rating, giving us some semblance of security that this brave decision wouldn’t be one of total regret.

Because the decision was so spontaneous and on a date night, needless to say I was not dressed appropriately to get a tattoo. I was wearing a lace pink dress that fit me snugly and covered my upper back where I wanted the tattoo, and the tattoo parlor we went to conveniently didn’t have anything substantial to cover me with. The tattoo artist said he would leave the room while I got undressed, and Chad promised not to “peek” as I took off my dress and wrapped it around me to cover my lower back (Chad later confessed to me he did indeed peek, which I think explains why he was all over me afterward). Just as I took off my dress, the tattoo artist yelled from the back, “By the way, there’s a mirror right to the side of you!” suddenly alerting me to the fact that my date could see all if he wanted to.

The tattoo artist, who was actually low-key hilarious, joked to Chad, “I’ve gotten farther with her than you have!” as he began adjusting my body accordingly on the chair to get me tattoo-ready. Let’s just say Chad was not a fan of this joke. As I laid almost face-down in my bra with my dress wrapped protectively around my backside, Chad videotaped me getting my first tattoo. I made sure not to make a sound or wince even though it felt like my upper back was getting drilled into by a machete. The tattoo artist – and my date – were both deeply impressed by my seeming tolerance for pain, especially as a beginner. As he got a front row view to the tattoo needles penetrating my skin, Chad remarked, “Katerina, I am squirming here just watching you! How are you not in pain?” I told him I was not going to let a little pain mess up the artwork. That day, I learned that men love danger because Chad couldn’t keep his hands off me the rest of that whole night. I also learned that tattoo artists have a distinctive sense of humor. When Chad and I went back to that parlor weeks later to get the tattoo touched up, the artist greeted me and quietly whispered to me as if we were part of the same conspiracy network, “Is that the same guy you came with before?” Always good to check, tattoo artist. We thank you for your thoughtfulness, talent, and service.

Danced on top of the original Coyote Ugly bar in a Little Red Riding Hood costume and six-inch heels with my girlfriends.

It was Halloween and I was out having dinner with a group of girlfriends. We were all in sexy little costumes and dangerously high heels, exploring as much of Manhattan as we could in one night, as one possibly can in stilettos. We decided we would visit the original bar in the East Village where the movie Coyote Ugly was filmed, although our plans didn’t extend much farther than that. The rest of the night was a bit of a blur, but after a few drinks, we decided we were going to dance on top of the bar, which is a perfectly rational decision to make after some tequila if you ask me. One of the burly men in the audience pulled me up to the bar and in my newfound gifted athleticism, I also began using the nearby horizontal pole above me to swing myself around on top of the bar multiple times in what my girlfriends later informed me were “epic moves.” (One thing I have to mention for you to understand this story, reader: I have better coordination when drunk than sober – I often joke that alcohol brings me back to my natural state, which is probably why I miraculously never once fell or tripped during this entire dangerous gymnastics routine even in heels.) Me and my girlfriends gave everyone in the crowd quite the Halloween show, but that wasn’t the only part of the night that bears mentioning. I had also drunkenly texted one of the guys I was dating at the time, the CEO of a SEO branding and marketing company who was all too happy to forego his boring plans with friends to join me that night. He arrived at the club just in time to see me spinning in heels on top of the bar and witnessed me being gently hoisted off the bar by the help of another muscular man in the crowd when I was done. Talk about a good night.

Got asked to have a ménage à trois by a hot Australian waiter.

New York has some of the best restaurants, and me and my girlfriends love fine dining. On one particular night, we went to a well-known Australian restaurant in Manhattan where we were served by a very hot and tall Australian waiter who kept staring at me flirtatiously and winking all night. He made sure to pay special attention to me as he took my order, deepening his voice seductively whenever he spoke only to keep smiling at me when he was serving other customers. My friends commented, “He can’t stop staring at you, Katerina!” and kept nudging me to leave my number on the receipt. I told them I wouldn’t do so unless one of them also left their number too – that way, we could play it off as a joke if he really decided to take any action. Of course, the waiter had no idea which number was mine since the receipt contained both numbers, so I guess he decided to take advantage of the opportunity (and is quite possibly a womanizer). At around 2 am, both me and one of my friends received a text while we were both in our respective beds: “I am off now! Ménage à trois?” Did either of us take him up on it? I guess you’ll never know.

Got kissed “swoon” style in midtown Manhattan.

I had just had one of the best dates of my life in a beautiful rooftop restaurant which doubled as a kind of “adult playground” complete with carousel, dazzling lights, thirty different bars, and a view of the Empire State Building right outside our table. My date insisted on walking me the twenty blocks to my apartment afterward, and on our way, he stopped me during one of our laughing sessions to kiss me passionately in the style of the infamous “V-J Day” photograph, not too far from the original location of the photo. This was definitely a whirlwind romance moment straight out of a fairytale, if not reminiscent of Carrie and Mr. Big (without all the pesky emotional unavailability).

Got frisky in the back of a Tesla.

On a different date with a different man, I got to experience my first ever Tesla. My date picked me up in it and we drove through most of New York. After a romantic dinner date, we inevitably had a steamy “makeout session” (that’s what we’ll call it for legal purposes) in the back of the car after parking it in a more secluded location near a bridge and underneath the stars. Luxury romance never looked so good. The Tesla was bright red, efficient, and beautiful, and I sincerely hope none of those built-in Tesla cameras ever keep records of that particular rendezvous.

Did a photo shoot in Times Square and got called princess by The Naked Cowboy.

I was doing a photo shoot in Times Square and it was actually themed after Sex and the City. I wore a frilly pink skirt, tiara headband, and gold sequin corset, posed like Carrie Bradshaw in front of yellow cabs (including the infamous opening credit scene where she looks down at her feet after getting hit by a puddle), and had a ridiculously wonderful time as strangers passed by cheering me on (including a shady guy who requested my photos from one of the photographers, a request the photographer wisely did not acquiesce to). But what really took the cake was when the Naked Cowboy in Times Square spotted me, kept staring in admiration, and called out affectionately, “Hello princess!” I felt truly blessed and anointed. I will tell my future kids that was the day of my baptism.

Danced on stage in a crowd of hundreds of people in a nightclub.

This story is quite similar to the Little Red Riding Hood story just on a far larger scale, so I’ll keep it short. No, I was not hired to dance. Yes, I was mildly inebriated, my friends did it too – and, yes the crowd loved it. Yes, I am a Sagittarius. There’s nothing quite like being on stage in front of hundreds of people dancing to your favorite music, and the crowd actually enjoying it and complimenting you afterward. (Note that presumably straight women have also told me I am a great dancer, so I know I have not just been hyped up unfairly my whole life by men who are interested in me. I have skills!)

Queried the owner of a midtown strip club with my girlfriends – and went to a male strip club.

These are two separate stories under the same theme. If you’re wondering why I have so many stories about strip clubs, you should probably stop asking questions (I also had an epic break-up in a strip club once, but that’s for an entirely different article). Me and my girlfriends were somewhat tipsy, wandering around Manhattan when we spotted a strip club, as one does in New York. We approached the “bouncer” guarding the door (is there such a thing as a strip club doorman?) and jokingly asked him what it would take to have a job there (emphasis on joke, as me and my girlfriends are all already gainfully employed in other careers, thank you very much). He did not hesitate and told us, “You would need to blow bubbles.” Confused, we asked what he meant. He clarified, “My name is Bubbles.” The quickness with which we all sped away from that particular establishment should be studied in a lab. On another fated night with a group of (different) girlfriends, we all dressed in black and headed to the only male strip club in Manhattan to watch half-naked, muscular men gyrating on stage, dressed as firemen, cops, and doctors a la Magic Mike. Unlike female strippers, however, these male strippers were far more aggressive about their hustle and kept approaching us to give us lap dances, which we did not want. One of my girlfriends joked, “It’s just not the same. He just gave that other girl a lap dance! I need more commitment.”

Dated five men at once.

I dated all the hot and slightly emotionally unavailable men in Manhattan so you don’t have to! But there was one specific time period in my life that I was dating more men than usual all at once. There’s a lot more to this particular tale and it was the beginning of my dating awakening. I invite you to read the in-depth tale here and what I learned about modern romance.