“I went on a date last night with a man named Jonathan,” I texted my friend.
“Oh yeah?”
“I think he’s your Jonathan…”
She had been telling me about a Jonathan for months. He was her husband’s best friend who had gotten divorced a little over a year ago - a great guy who was really serious about finding his next partner. She had a feeling we would be perfect together, and she promised that when the timing was right for both of us, she would set us up…it just hadn’t been right yet.
But the universe had other plans. We met on our own.
Our first date was exactly what you would envision a perfect New York City date to be. A table tucked into a nook at a dimly lit, crowded restaurant while two strangers, ensconced in the energy of a magnetic connection, unaware of anything else, got to know each other.
We talked about all the important things. Things that define compatibility and intention.
Do I want kids? Does he want marriage? What is his custody situation with his three children? Do we want to stay in the city? How do I feel about living abroad several months a year? Do I believe in the moon landing? Should I make up with my sister?
It was clear from the start: both of us were looking for the real thing, and the same thing.
Each question brought forth a new, effortless access point for connection. He didn’t feel like someone I had known my entire life; he felt like someone I wanted to know. And someone who also wanted to know me. Flashes of hope began to illuminate my body as - after a very long time - I started to come alive again.
My friend was right: we were perfect together.
He kissed me goodbye, and I let him, but I walked home with an unfamiliar uneasiness. Like something was missing.
There wasn’t that usual inner churn, or an impulse to rip his clothes off. Maybe I’m not attracted to him?
There wasn't any anxiety about if he liked me or not. Maybe I don’t like him?
The answer to both of those questions was no. And I realized that my uneasiness was actually calm. I was calm.
Right as I got home, he texted to say he couldn’t wait to see me again. We decided to take a walk in the park on Saturday - it was forecast to be the first warm day after the longest, darkest winter. The perfect metaphor.
I slipped on a sundress and a pair of Converse to meet him at the Aman in midtown. We met in the lobby, and he kissed me on the cheek as we rode the elevator to the rooftop for a quick bite before our walk.
“I don’t really like anything on the menu,” I grimaced. “Maybe they can just make me an egg?”
He waved the waitress over and asked if the kitchen would make us breakfast.
“My father used to tell me that if you want something, you should ask for it,” he said with a smug smile after she brought us the menu. “You’re giving people an opportunity to make you happy, which makes them feel good.”
Noted.
One AMAZING gluten-free pancake and a matcha latte later, we walked across the street and into Central Park.
We meandered along the windy path he walks every day after work. We talked about the deeper things. Glimpses of our childhood, and the people and experiences that shaped who we are and why we are the way we are today. He stood behind me and wrapped his arms around me as we watched a group of people do tricks on roller skates, and I leaned back into him, closing my eyes and letting the moment move through me.
It was only our second date, but both of us could tell that there was something special about our burgeoning connection. “It feels good to be with you,” he said.
“I know,” I sighed, feeling every ounce of how hard I had fought to keep believing that a moment like this would ever happen for me again.
As we walked towards the park exit, we talked about our past relationships and what we were looking for in a partner.
“I need my partner to be my anchor,” I said, as a flurry of butterflies unleashed in my stomach. I inhaled before sharing the part that scares me the most:. “I have been alone for so long, and I am not meant to be alone. It’s been a disaster. I need to be with someone who will take care of me and do all the things that I think are hard, and who will let me do all the things that he thinks are hard. I still believe in gender roles, and I want to be someone’s wife. The kind of wife that makes an intentional and beautiful life, and who creates the conditions for my husband to be everything he wants to be - beyond what he could accomplish on his own. I know that’s not very New York City or 2025 of me to say, but there is nothing more I want in this world than to love someone well, and to be loved well in return.”
“That is music to my ears,” he said, and my stomach relaxed. “When I think about what I want, it really comes down to one word: peace. I understand being human, but I really just want a peaceful life with a woman I love. Someone who loves me and who likes spending time with me. I want to look forward to coming home to her, and for us to just feel easy together. And it would be great if she helped me be a better man.”
“I kind of think wanting your partner to help you become a better version of yourself is a baseline expectation,” I said.
“You’d be surprised,” he mumbled as he grabbed my hand and we walked out of the park and into the chaos of the city.
“I don’t really want to say goodbye yet. Do you want to get something eat or a drink?” he asked. It was hot and both of us had been sweating since we left the Aman. “Actually, would you mind coming up to mine for a minute so I can change? I live two blocks away.”
“I can wait for you down here while you change,” I replied. “And then we can get something to eat.”
We walked in the direction of his building and he cleared his throat. “I have something to tell you about my living situation.”
Oh god.
“I have a whole floor, but it’s divided up into different apartments. My housekeeper lives in one, my trainer lives in another, I have a friend in the other, and another friend who lives with me.”
“You have a roommate!?” I didn’t even know how to compute that. I was on a date with a 47-year old man who has a roommate??
“He’s super cool, and he’s never really around. It felt weird to live alone after my divorce. I got really lonely. So this arrangement just sort of happened and it works for now.”
“Oh,” I said, getting lost in trying to imagine how something like that might work.
“Are you sure you don’t want to come up? It’s so hot out. We don’t have to do anything - I’ll just change and show you around and then we can go.”
“I need you to understand something,” I could feel myself stumbling over the words I needed to say before any of this went any further. “This is a big deal for me. Being with you - on a second date - is a big deal for me. I haven’t dated in over a year because my last relationship really messed me up and I wanted to make sure I never experienced anything like that again. I want to do things right, and I need to go really slow. This is really important to me, and I know you’re just changing, but if I come up, I need you to hear that and I need to know that you respect that.”
“I hear you and I understand you and I totally respect that,” he said, his eyes locked on mine.
I believed him.
We took the elevator to the 54th floor and walked out into a dark and moody hallway. He pointed out everyone’s respective doors and I wondered why he needed to share an actual apartment with someone when he was already living with so many people.
Is this a red flag, or should I give him a pass because the transition after divorce is hard and it shows he can share space with people?
We walked into his roommate-free apartment, and he gave me a little tour. He opened up the door to his bedroom and flopped down onto his enormous bed. “It’s a great view, right?” he nodded towards the window. I craned my neck to look out at the Louis Vuitton installment and over the park. “Very cool,” I stammered, frozen in the doorway.
“Don’t be freaked out,” he said. “Nothing is going to happen. But you have to admit the AC feels good and it’s a lot easier to talk here.”
He was right. I much preferred the quiet stillness of his apartment to the busyness of a restaurant. We could get to know each other more this way.
I walked over to the window. “You know, if I were ever to stay here, I would want your side of the bed. You need to be closest to the door to protect me from intruders.”
He ceremoniously moved over and patted the spot next to him. “Why don’t you have a chair in this room?” I asked, trying to delay what seemed to be inevitable. “You’re still in your sweaty clothes. I thought you were going to change.”
“Stop and just come lie down. I’m not some monster who is going to attack you. It’s just more comfortable here.”
“Maybe for you,” I rolled my eyes as I crawled next to him, his big arm pulling me in. My entire body relaxed against his. The aching loneliness that had been living in my bones for the last year dissolved. I put my hand in the palm of his and he laughed, “My hand is the size of two of your hands.”
And then I forgot the rest…
Until it started getting too close to where I knew I definitely didn’t want it to go.
“Okay, let’s go get a drink,” I said, with his mouth still on mine. “I really don’t want to do this.”
And then I forgot again…
Until I remembered again and pulled myself out of bed. “Where should we go?” I tried to brush the wrinkles off my dress as I walked towards the door. I froze when I heard the sounds of a March Madness basketball game.
We did not turn the TV on.
OH MY GOD HIS ROOMMATE IS HOME.
I wondered if I could just jump out the window. “Why don’t you have a second exit?”
“Relax,” he laughed and flung the door open.
Relax!?
“Hi Cici! It’s so nice to meet you. I’ve actually been wanting to talk to you. Jonathan said you’re a novelist…” his friendly voice boomed as he shook my hand.
“Well, I’m writing a novel, but I don’t know if I’d call myself a novelist,” I said, feeling all the humiliation in my body instantly disappear.
He actually was super cool.
We walked back into the Aman, hand in hand, and he kissed my neck as we rode the elevator to the rooftop.
It was crowded and loud, which was exactly what we didn’t want. My skin prickled with anxiety as we walked towards the hostess station. “Hey, I know the bar upstairs is technically closed, but do you think we can get in and have someone bring us martinis?”
“Well, I know it’s your birthday next week, so for you, of course, Mr. Stern.”
He turned to me and smiled. “See!? If you want something, you just have to ask for it.”
She led us up a narrow stairway into a dark and quiet bar. We sat on a cushioned bench and he ordered us dirty martinis. I tried to remember the last time I had a drink…
A few minutes later, Jonathan got a text from his roommate.
He smiled and showed me the phone: “She’s cool!” read the white bubble.
“I think my friends think we are already together, like a couple,” he said.
“It does kind of feel like there’s something real here. I could see us evolving into a couple,” I answered.
“I love that, and I feel similarly. I’m actually really comfortable saying that I want to explore that with you and don’t want to date anyone else. We should be exclusive.”
“That’s a little fast, no?” I felt my face start to get red. It wasn’t that I didn’t feel the same way…I just wanted it to be slow so I could feel like he was choosing me, and not just landing on me. And also, this was the first date I had been on in a year. Maybe I wanted to date other people so I could choose him, too.
He looked at me, expectantly. “Are you saying this because you know I won’t have sex with you unless you do? Because I’m still not going to have sex with you. My last relationship really messed me up in that way, and I need to make smarter decisions if I want to have better outcomes,” I said.
“I want you to have sex with me when you feel ready to have sex with me.”
“I promise it will be way better that way. And it’s hot to wait…it’ll be worth the momentary frustration,” I smiled.
Our drink turned into dinner and we walked down the stairs to the Japanese restaurant, where we requested to sit somewhere we could be next to each other.
“I like this,” he said. “I love that you’re affectionate with me.”
The night blurred into stories of our wild younger years, and as he was recounting his lavish, celebrity-filled nightclub summers in the South of France, something inside me clicked.
“Wait, stop. You know I’m not from that world, right?” I said, in reference to the extraordinary circumstances of his life. “I’m just a girl from Connecticut. If you need someone who is into all that, then we need to stop now.”
“That is actually music to my ears,” he said, and then paused before going deeper. “I lived that life already. I married a model and we did that, and it didn’t make me happy. I am not looking to repeat it. I am looking to downshift into something that is real and brings me peace,” he said, taking my hand.
“Okay. But just so we are clear: a downshift is not a downgrade. Because if I let you in, I am bringing you into a world that is so full of love and magic and connection and beauty and art and it is so precious and priceless. You could never buy your way into the world I live in. You are still dating up.”
“I know that,” he grinned, and kissed me.
He ordered saki, and I asked for sparkling water. I got a fun buzz from the martini, but didn’t want to get drunk. The night felt too special, and I wanted to be present for it. Plus I take Ambien at night, so I didn’t want to mix too much.
Plate after plate was brought to our table, and at one point I noticed that he seemed rather intoxicated. Or at least weaving in and out of presence.
“Are you okay?” I asked him, and called the waitress over to over some water and a bowl of rice.
“I’m totally fine,” he protested, but ate the rice anyway.
He wrapped his arms around me on the street outside his building. “I don’t want you to go. Please stay the night. I just really want to sleep next to you.”
“But I don’t have any of my stuff, or any pajamas. And for as much as I would love to stay with you, I really think it’s time for me to go. I really like you. I’m really excited about you. I feel like you could restore my faith in men. But I need to do things differently and really take my time.”
“I really think you should stay,” he persisted. “At least come up and hang out for a while. And if you decide to stay, we’ll Door Dash your stuff and I’ll give you something to sleep in. It will all be very PG. It would be the perfect way to end the perfect day. And even if it did happen, I’m not a runner. I know what I want, and I want you.”
I knew I wanted him, too. And of course I wanted to stay. I wanted him to hold me all night and to wake up next to him. It was really hard to say no. So we walked inside.
He introduced me to the elevator operator as we rode up to the 54th floor. His roommate was there when we got home, and we all sat and talked for hours before bed. I relaxed. Jonathan was wonderful. I smiled as he handed me a pair of his boxers and a t-shirt. I popped my Ambien, and got into bed. He curled up next to me and rested his arm over me. “Goodnight,” he said.
“Jonathan, please. I don’t want to do this,” I pushed his hands off me in a groggy haze.
“What do you expect from me? You’re gorgeous and you’re in my bed. I can’t help it.”
“Yes you can. Please let’s just go to sleep. Please. I’m so tired.”
But he didn’t stop. Fighting with him was exhausting. And my limbs were heavy with Ambien.
I had roofied myself.
“This was a huge mistake. I never should have stayed. Doing it this way will make me not like you. I actually am a runner, and this will make me run,” I said as he pulled my boxers down. I pulled them back up. He relented. I drifted back into my beckoning sleep.
I woke up with him inside me and started sobbing as I jerked my body away from his.
“Please stop,” I whispered through my heaves. I was trapped. The door seemed so far away. Sleep kept trying to pull me into the undertow.
“I’m sorry,” he said, rubbing my back. “I’m sorry. I’m so turned on by you and I am having a hard time controlling myself. I’m sorry.”
“Does it turn you on because you know I don’t want it? Why do you want to have sex with me when I don’t want to have sex with you?” I asked, wiping tears off my face.
“I’ll stop. I’m sorry,” he said.
“Go sleep on the couch,” I mumbled as I was pulled back into a dream.
And the cycle began again. And again. And I just wanted it to be over.
“Okay fine,” I said, taking my top off. “Just do it and get it over with,” as I pulled off my shorts.
And I lay there while he did.
I didn’t hate it. It wasn’t like I didn’t want to have sex with him. I just didn’t want to have sex with him that night. But we did, and it wasn’t awful. It just wasn’t what I wanted. But I also didn’t not want it…
So when he woke me up in the middle of the night, I reached back for him. And then again…
It was 1 pm when we finally got out of bed.
“I thought you guys were dead,” his roommate said when we walked out of his room. I looked out the window into a gray sky. The warmth of Saturday had been replaced by an icy chill, and all I had was my sundress and a pair of Converse.
“Let’s hang out later this week,” he said, bringing me an oversized hoodie to cover up with. “It’s my birthday on Wednesday and I have friends and family coming in, so do you want to try for Saturday?”
The doorman smiled at me as I scurried out onto 5th Avenue. The air felt good on my legs as I walked home and tried to process the night.
It’s a big red flag but I really like him so I can find a way to make it okay it’s a real problem and I don’t know how I can be okay with it I can’t tell anyone - everyone will be so mad at me but I have to tell them, fuck - why does everything have to be so complicated? Why didn’t I listen to myself and just go home? Why couldn’t he have just waited? But what if it actually works out, though? I was probably going to need some pressure to have sex again no matter when we did it, so now it’s out of the way maybe I just won’t have sex with him again for a while it’s going to be okay he’s a good man and he came with references I need to calm down and just let it play itself out and trust that it was supposed to happen this way otherwise it wouldn’t have.
“I wouldn’t have introduced you to him yet. I wish you guys had gone slower. He’s really messed up from his ex,” our mutual friend said when I told her what happened. “But he’s a good guy so don’t stress about it. It’ll be okay.”
He called me that night to say goodnight, and the red flag turned orange.
It’s not like it was nonconsensual.
He texted me from work and called me the next day. The flag turned yellow.
I think can let myself like him.
On Tuesday, I sent him a happy birthday text at midnight.
I am really excited to see him on Saturday.
You’re so calm,” my friend said. “This is so unlike you. He must really make you feel safe.” The flag was now green.
I got my hair cut and a blowout on Friday. I waited to hear from him about our weekend plans. I hated that I was waiting. Why was he making me wait?
Something didn’t feel right.
I know this feeling. Stop feeling it, or you’ll make it come true.
I looked at my phone.
I went for a walk.
I watched TikTok.
I made myself dinner and immediately threw it out.
I went to bed.
My phone stayed dark.
His brother is visiting from France. This makes sense. It’s okay.
By noon on Saturday, I texted him:
I once heard someone say that Tuesday was the night she would give men who had pissed her off. “I am free on Tuesday,” I wrote, not wanting it to seem like my world had suddenly become very empty.
Sunday.
Monday.
I hadn’t eaten or slept since Thursday. I was firmly in the grip of my own nightmare. The echoes of past betrayals turned into deafening screams as they dragged me into a full body trauma response.
Tuesday.
This is insane. I need to make it stop.
Wednesday. Thursday. Friday. Saturday.
Sunday. Haggard, exhausted, my thoughts had not stopped racing. I couldn’t stop moving. My body was depleted, and my already underweight frame started to shrink into nothingness. I needed to get myself out of this or else my physical health would not recover. I had been in this loop before, and it led to the biggest and most sustained health crisis of my life. One I had just finally worked my way out of.
That night, I slept.
But then: we have mutual friends. We will absolutely see each other again. I can’t just leave it like this.
“Saturday on the West Side Highway,” he said.
“Great. I will look forward to it,” I replied, not knowing what outcome I actually wanted or if I would even go.
“Me too.”
Tuesday. Wednesday. Thursday. Friday. Saturday…