Don’t Date the Guy in Your Building
Caveat #1: I do not encourage any of his behavior or mine.
Caveat #2: These are not my green flags or hallmarks of my future husband.
Caveat #3: I have just wanted to write about this story and my feelings for awhile.
When I first saw him, it happened in slow motion
I just moved into my Upper East Side apartment that summer. 3 bedroom, 2 bathroom and mine was the corner bedroom with sunshine pouring in from the east and south sides of Manhattan.
Finished my Sunday long run across the Queensboro Bridge to Long Island City and back, I was walking up my block with my iPod still blaring in my ears.
I saw a black SUV pull up to the entrance and the back door swung open. A tall guy wearing long pants in this NYC heat and a casual t-shirt stepped out.
The second thing I noticed was that in his right hand he held a thick paperback book and wired earphones. My eyes stayed on what he was holding as I felt him look back at me when he got fully out of the car. This entire moment of noticing him felt like it happened in slow motion.
On an underlying level, I feel sexy after runs but on that particular blazing afternoon in the hot sun, I felt shy. I was sweaty, hair pulled back, no makeup, face red, acne scars visible, and haven’t fully caught my breath yet.
Now by mathematical fact, he should have got to the building entrance before I did— having gotten out of a car that was parked right in front of our carousel door and his stride being longer than mine. But I knew he purposely slowed down because even though I was paces behind, I somehow got to the spinning doors before him.
I pushed the door and the whoosh of our air conditioned lobby relieved me.
I walked down our long hallway to the elevator bank, half hoping he’d stop at the front desk to pick up packages or something so that we didn’t have to stand next each other.
I felt nervous.
We were the only two residents waiting and got into the same elevator. I pressed 8, he leaned over and pressed 22.
I lowered the music on my iPod and stood close to the floor buttons just looking at them. I could feel him in the back of the elevator as we climbed the floors— 2, 3, 4, and he said, “wouldn’t it be really messed up if there was an opposite club?”
I felt my eyes light up that he spoke to me but I didn’t turn back right away because I was trying to process what he said. In a millisecond, I remembered what I was wearing. A black shirt that had the phrase in massive lettering “anti-racism running club” on the back.
I smiled and turned around. He gave me a smile, holding eye contact well and the corners of his mouth pulled back.
That's when I first really looked at him and thought okay he’s good looking and he looks kind.
“Yeah,” I laughed and mentioned I had just moved in.
Elevator doors opened to my floor and I said bye and stepped out when I heard, “I’m hosting a bunch of us on the rooftop this summer. Want to give me your number so I can invite you?”
Still holding his book, he shoved his earphones in his denim pocket and used his other hand to force the elevator doors to stay open. He handed me his phone and as I typed in my name and number, I heard the heavy metal doors rumble, yearning to shut, and continue its ride up the building. He stubbornly held one side open, looking down as I typed. I liked this so I didn’t rush with my typing either.
“Here,” I said feeling a little off-guard, remembering I was sweaty and no makeup.
“I’ll text you right now,” he said with his kind smile.
Before he could see me blush, I turned around and started to walk towards my apartment feeling thankful and happy that I had already made 1 friend in the building within my first week of moving in. I could feel my cheekbones sky high with me smiling.
Wednesday nights with my finance guy
As promised, he texted.
But only to make plans and never any real conversation was held in our blue and white bubbles which is what I like. We were also neighbors so on principle if we wanted to talk about our day, it just made sense to hang out irl.
I smoothly entered a rhythm with this guy.
We’d hangout on most Wednesday nights. I worked in tech and finished at about 6, sometimes 9 if I hosted an event.
He worked in finance and finished at 9, often later.
I’d already be home when he would text after he got home and would invite me over. Some nights I went in my same work dress to avoid trying too hard and other nights, I’d change into something more light for the NYC summers, even though we were barely ever outdoors without AC.
On the first night when he invited me, I came up to his apartment and knocked on his door. I could feel slight jitters and took breaths to calm myself.
He opened the door still in his work clothes but shirt loosened. Behind him, a few of his friends were standing with drinks and passionately discussing something, laughing together and debating at the same time. For 10pm, there was a lot of energy in the place.
He introduced us– me as his neighbor and them as his friends from work. They all worked at the same firm and shared relief about finally finishing the work day, though I’d watch them often check and send emails throughout the night.
“Can I get you a drink?”
“Sure,” I replied.
I’m a lightweight, like a 2 wine glass max kind of girl though I never shared that with him.
His apartment was well sized, a 1 bedroom with tall ceilings. He also offered me food he bulk cooked earlier that week. He had a wide bookshelf - major green flag - with all your typical personal development books, Harry Potter series, and other fantasy novels. Board games, card games, and on his coffee table, an astrology book that he said a barista from Europe sent him.
Like all finance bros apartments, he had the type of standing desk setup that looks like a spaceship command center with multiple monitors and his black backpack plopped next to it.
I accompanied him in the kitchen and watched him make me a martini. His white shirt sleeves were pushed up to show his forearms the way most women love to see it on a man. He confessed how he was influenced by Blake Lively's “A Simple Favor” movie when it comes to martinis as he pulled out a glass from his freezer, whisked citrus peels, and poured me a generous amount of alcohol. I cheersed with his friends and painfully sipped.
Not long after making our first drinks, he asked me if I wanted another. I said no. Obviously there was no way I’d even finish this one and leave here OK.
They finished their drinks, he took my half glass from my hands, and called us an Uber Black to Bemelman’s which I thought was funny considering we lived less than 10 blocks away.
We all went to put our shoes back on and when he sensed some of us flustered and rushing he goes– “don’t rush, the car will wait” and I loved that. I feel like in NYC there’s always this sense of hurry but not with him.
We waltzed through the lobby and all four of us packed into the back of the SUV. He asked for the aux and blasted Harry Styles. Interesting choice, I remember thinking. He reached over me, hit the button to open the tinted car window all the way down, and unapologetically leaned on me to lean out of the car for a moment.
I could feel myself swoon for a guy who knew how to be alive.
We pulled up to The Carlyle, the song not even having finished because it was like a 2 min drive. The doorman welcomed all of us. I could see him linger in eye contact like he was trying to see if the doorman recognized him but he gave no such signal, just a general warm welcome. We shuffled into the bar, jazz music playing, standing room only, velvet carpet, beautiful art, and immaculate vibes. I haven’t been here in years.
He led me by the small of my back and guided me to a spot where we could stand comfortably and then disappeared as I stood there with his friends who were trying to understand what exactly I did for work as a Head of Community at a pre-revenue tech startup in Soho. Meanwhile, he himself never once asked about my work. Really, never asked.
He came back with 2 espresso martinis and handed me one then signaled to his friends that their drinks were at the bar.
As I stood there for a brief moment while they swapped places, I returned a stare I felt from across the room.
Two guys holding drinks and one of them looking directly at me.
Flattered, I could feel myself smirk. He followed my eyes to them and back to me, “do you want to talk to them?”
I didn’t say anything but pretty sure my face said something.
He smiled and went over to them and then they all walked back over to me, where I was rejoined by his friends who picked up their drinks. The group of me in my one piece and them in their finance attire was expanding.
For what it’s worth, I didn’t want to talk to the two guys. I just didn’t want him to think he had all my attention. I needed him to earn it.
But then he actually brought them over. Great. Up close, they were boring vibes. Our group conversations sort of split because you need to lean in to hear anything with the piano and the saxophone and the laughter and flirting and business talk all happening in uptown Manhattan’s elegant living room. The guys tried to talk to me about what they did for work, the zeitgeist in real estate equity law I couldn’t care less so at a certain point, I just stopped replying and smiled, “I’m so sorry I can’t really hear you.”
I diverted my attention back to him, which he welcomed, and said, “now pick someone for me to go talk to.”
A game, I thought, I’m good at these.
“Her,” I said looking at a gorgeous tall woman in a high neck sleek evening dress standing at the bar. She was holding the back of the bar chair that her friends were sitting in, looking radiant and very present in conversation. She was a bit older and looked very unbothered when he went up to her.
I didn’t want to stare or make it any type of obvious that I was the one who instigated this so I kept my body language and direction toward our little group.
After some solid minutes, he came back, “I told her that I was only talking to her because you dared me to but I really want to talk to you and how I think you’re beautiful.” Out of flattery, I looked away from him blatantly smiling. “She thinks you’re beautiful, too.”
We all chatted some more and I sipped the strongest espresso martini I’ve ever had.
“We should eat,” he said to everyone as he whipped out his phone and called another Uber Black. I hadn’t eaten dinner yet and it sounded like none of them had either. He closed us out at the bar and we hopped back into a car headed downtown.
I think were in the Lower East now. We all got out, his friends heading straight into the restaurant. I stepped out of the car, smoothed out my dress, and tried to look up to see the name on the storefront but it was so dark.
He was in front of me as I walked into the restaurant and then, he reached his hand back, and I slipped mine into his— smiling, a little flustered about it, and honestly kind of proud. There’s something so hot about a guy who reaches his hand back, wanting you to take it.
A combination of him being slightly in front and leading. His tall build. His confident posture. The ease in which he moves through this city.
Every time he did this, I would forget whatever restaurant or bar or club we were going into because it felt like all that existed was us, just me holding his hand.
Back to the night— so we enter the restaurant and he leads me to the back to a side room where there’s 1 long table against the wall. We all scoot in like bar style almost omakase seating, I’m next to his friends and he’s a bit further away. He orders us extra dirty martinis and we order our mains– a lot of us getting the steak. It’s somewhere between 11-12am as I do some quick mental mental math on what time I’d get home, get ample sleep, and be at the office the next day.
As we waited for our food, new people joined us in the private dining room who came up and said hi to him and his other friends. Like 3 girls in their cute fits. Their casual wear was so ambiguous, I couldn’t tell if they were swinging by to say hi or if he invited him for dinner, too. Since he was seated at the other end of the table, I mostly talked to his friend as he laughed and chatted up the new company we had.
I didn’t finish my food and was losing interest in the night.
“I think I’m going to head home,” I said to his friend. Then, my neighbor suddenly swapped seats and sat next to me to change my mind about leaving.
It was after midnight and there was every logical reason to be turning in now.
I’d only want to stay out if this night could get more fun.
“I want to go dancing.”
With one hand on the back of my chair and the other on the table, body fully turned and open to me, he smiled and then looked across the table at his friend, “where should we go?” His friend listed off some spots and we settled on one, the guys enthusiastically agreeing. They got the bill and we left.
As a group, we walked less than 2 blocks and he opened the door to what looked like a quiet place, letting me in first. I showed the bouncer my ID and started to walk straight in when he touched the side of my waist and said, “downstairs” and opened up another door where the music was bumping.
I arrived on the dance floor and was hit with a surge of energy.
Along with his friends, we took the center spot joining the other people who were dancing. There was a small bar, a disco ball, the place was dimly lit, and the music volume was perfectly loud. For a Wednesday night, this place felt alive.
One of his friends called out to us waving us down to come to the bar where we took a shot together.
I immediately regretted it and retreated back to the dance floor.
I had no idea what songs they were playing but I was vibing with everyone. I also had no idea where he was. Shortly, he emerged to us in the crowd and started to dance with me. I was wearing my dark silk skirt that night and could feel him behind me when we grinded. At one point, he started to dance more playfully, like couples do at weddings in an open dance floor than a crowded club one. “I didn’t know you could dance like this,” he said and I’ve heard this many times before.
He spun me around and I felt like I was in a movie.
Then, it all started to get too hot. The alcohol was not sitting well in my stomach and was starting to get to my head. I left them on the dance floor and went upstairs to get some air.
When I got the sidewalk, there was taxis in traffic, couples standing close, people smoking their cigarettes, and downtown Manhattan was all lit up.
He came up shortly afterwards and joined me. One of the friends too who was trailing right behind him.
“Sorry I just needed to get some air,” I explained and didn’t want to think that I was going to be sick.
He took me by my shoulders and we walked around the corner into a late night whiskey bar. It felt like upscale hotel lobby but without a check-in desk and any guests. There was only 1 other person at the bar and compared to the other place we were just at, this place was peacefully quiet. I could have fallen asleep right there on the plush seats. He ordered a drink for him and his friend and knew better than to get me anything else except water. As the bartender prepared the drinks, he started to talk to the other person who was the bar alone.
I felt like I needed to throw up so I dashed out around the corner. Holding the metal scaffolding bar, I dry heaved and nothing came up.
His friend chased me and said we’re all just going to go home but that I needed to throw up first so I didn’t do it in the car ride.
“Nothing’s coming up.”
And for the first time in my life, this guy took his 2 fingers and shoved them deep down my throat properly enough that I instantly vomited all over the curb. Then he did the same. I could only imagine what it looked like– 2 people throwing up under scaffolding at 3am in the morning.
The drinks, the dinner, that day's lunch, everything was splattered on the pavement.
I felt better and thanked him.
We stood up with straight postures when I saw my neighbor turn the corner in a semi-jogging pace and spot us, “I was wondering where you guys went!”
One real look at us and he turned toward the avenue and hailed an uptown bound taxi.
We dropped off his friend somewhere in midtown and we both stayed in the cab to continue uptown. My arm was completely intertwined in his and my head rested on his shoulder, I was falling asleep, feeling safe and happy, as I felt NYC lights rush around me.
“You can just drop us off here,” I heard him say.
He pulled the sliding taxi door open and we both got out. I couldn’t tell where we were except that it was one of the main avenues but from the quietness, I knew were back in Upper East.
“Look, there’s always a cat here,” he pointed out to me in this cute boutique plant store that had all its lights off. Indeed, there was a cat, wide awake, laying on its side and its tail tapping the ground, looking happy to see our drunk faces.
He put his arm over my shoulder and suddenly seemed more drunk than he did than the entire night. I put my arm across his waist just to make sure we both walked straight.
There was a point as we walked that he looked down and in the most emotional tone I had heard from him, he goes “look we’re even walking in lock steps,” as put more of his weight on me.
We got into our building, rode the elevator and he pressed 22 and then I pressed 8 and he gave me a look of disappointment.
“You’re not coming over?” he asked.
“No, I have work in the morning,” I soberly answered.
I got out on 8 and thanked him for a great night. Truly. He took me by my hand and said he’d walk me to my door.
Being a corner apartment unit, I’m down 2 very, very long hallways.
We walked quietly, neither of us talking.
I felt the tension build.
Before we made the second turn, we stopped at a long stretch between 2 apartment doors and he pinned me on the wall.
Fuck, I thought.
Don’t kiss him, this is your only friend in your new neighborhood.
Drunk, if not at least tipsy, he pressed his body up to mine and looked straight at my mouth.
“We’re friends,” I said quietly.
“I know,” he replied, still looking at my mouth.
I could feel my breathing change as his grip tightened on my wrists.
My body acted before my mind, fuck it, and I tilted my chin up and kissed him and felt him kiss me back passionately.
roommates group chat, ft. when I’d go upstairs to say hi to him but then we’d go out dancing
This was kind of our routine
He’d text me when he got home from work, which was often late.
We’d start in his apartment to catchup on our day.
Then he’d call a car to the The Carlyle for drinks.
And then again to dinner downtown, where he’d divert his attention toward other women.
And then dancing, where he’d give me all his attention.
And then home to our separate apartments.
And there was never a night that was just us.
We always had company. He seemed to successfully rally friends or colleagues every time. I assumed his finance friends also needed to let loose midweek.
And then it all sizzled out quickly
One Sunday morning, I laid in bed feeling under the weather and got a text asking what I was up to. Unusual, I thought, since we only hang out midweek and at night.
I didn’t want to be his girlfriend. He was sweet, strong EQ, great income, family in NYC, but there was something about him that wasn’t grounding. He was great for these midweek night fun moments and kissing but for picnics, growing something, hard times, actual support, and traveling– I didn’t see it. And I’m someone who can tell in an instant when I meet a man if we’re going to date or not. I knew we might have something fun but we’d never be with each other.
So when he texted on Sunday I thought it was strange. I said I was in bed and feeling sick and he texted me to come over and cuddle.
I love cuddling.
I changed into cuter pajamas, brushed my teeth, and went upstairs.
He had left his door slightly opened already so I walked in and joined him in his bed.
Unlike my bedroom, where my shades were all opened and the late morning sun poured in, his were tightly shut and the place was dark. The apartment where I started so many of my social midweek nights was pin drop quiet and for the first time.
And it was just us.
He cuddled me close and I loved how warm he felt.
We got intimate for the first (and only) time and in complete transparency, it was bad. It was the second to worst time I ever had. From a lack of emotional connection and sexual chemistry combined, I didn’t feel anything. He also said something to me that turned me off and not just sexually but turned me off in general, like an expression that showed he never actually GOT me.
And it was true. He didn’t really know me. We didn’t know each other.
We were always around stimulating, exciting environments that we did not have to rely on each others stories or energies to feel each other out. The world he led me into was nightlife playground that I thoroughly enjoyed and consumed weekly.
Mornings after hanging out with him, I would do my makeup for work and notice how inflamed my face was from the 12am dinners and all the alcohol and lack of sleep.
I think we both felt how awkward that was for us afterwards.
Don’t date the guy in your building, the NYC homage
We still lived in the same building and I dreaded seeing him in the laundry room, which only happened like twice.
Then when winter rolled around and I’d walk into the building and see him flying out the doors, breath catching in the frozen air, rushing toward a car that always waited anyway.
I am thankful for the entire experience as I am with all my romances.
One of the grandest perks that came from this is that I eventually became a regular at Bemelman’s on my own (I still call it The Carlyle because it rolls off my tongue easier). I was such a regular, I celebrated one of my birthdays there, I got invited to the bar manager’s birthday at another uptown bar and got to meet a whole bunch of new people— both locals and visiting. It kind of became my living room and I’d wrap up late nights at The Carlyle in general.
Christmas was my favorite because of how they’d decorate the lobby and bar and the coziness of the music.
UES was the safest neighborhood I had ever lived in and in the beginning, holding his hand was a part of it.