Virtually In Love

A Single Girl in New York City, just trying to do her best to avoid dick pics.

I met “Jordan, 34” for the first time after nine months of a virtual friendship, slash I have no idea. We had connected on a dating site for single Jews- a kosher tinder that was all the rage in New York City. He looked handsome in his pictures. A photo with a warm blue filter. He was standing on a concert stage in a suit. He looked confident, with a kind smile, a flirtatious smirk, tall, with broad shoulders. I was intrigued and ignored the “Philadelphia, PA” location listed in his profile. He messaged me, “Hi…Pretty Smile.” He quickly asked for my number and we began exchanging texts. He was a great conversationalist, a rare to find in online dating. After a few hours of messaging on a Friday afternoon, sitting at my desk — my phone rang. I let it go to voicemail and grabbed my bag so I could leave the office and return his call. I couldn’t wait to listen to his voicemail.

“When a man is interested in a woman — he should call her. Why don’t men call women anymore? So this is Jordan. Call me back.”

I was already intrigued by the confidence in his voice and his message. I dialed his number back. He answered right away. I walked in circles around my neighborhood chatting with him. In town on business, he was in an Uber to some networking event in Hoboken. He made me laugh on the phone. His confidence was infectious. About half an hour into our conversation, he made a confession.

“I don’t know if this is a big deal or not. But, I’m technically married.”
“Not like married…married.”
“I’m separated.”
“I’m going through a divorce.”

I had a million questions but asked none. Finally, I replied.


We continued to talk about nothing and everything, and then Jordan said something that would make my stomach drop. “I don’t want to get ahead of myself… because it seems a little early to talk about traveling back and forth on weekends..but you know travel would obviously be part of our relationship if we were going to date. Ya know, and like make this work.”

Had I met someone who said the things you aren’t supposed to say in the early stages of meeting somebody new? Could he actually have realized how wonderful I was from this brief interaction? Ready to start his busy weekend, he said goodbye, and I hung up the phone. I walked back towards my apartment and began to imagine myself heading out of the office on Friday afternoons to Penn Station, hopping onto the Acela, and running up the stairs in a Rocky-esque victory to meet my new love.

I watched my phone all weekend, waiting for his text. On Sunday morning, it finally arrived.

“Hey you… This hotel bed is all sorts of comfy. Room service? ”

He started sending me selfies of himself lying in bed. He had an adorable smile. He offered up his credentials — hometown, degrees, place of business, mutual Facebook friends— and assured me he was a nice guy. I explained that there are few guys who didn’t make that claim before they ask to see you topless. I resisted. I saw potential in him and tried to think of topics that might keep him interested that didn’t include me agreeing to breakfast in bed.

He left New York, without us meeting in person and I felt regret. I continued to text him and soon I found myself completely consumed with our text exchange. I added him on Snapchat and would send him pictures as I got ready for work and for nights out. He always replied to tell me how pretty I looked. It was welcome attention.

Jordan’s confidence and charm was soon to much for me to ignore. It was a Tuesday and I had woken up in Jersey City after a promising third date. I could tell the man sleeping next to me was awake, but he kept his eyes closed as I quietly found my clothing, got dressed, and slinked out of his apartment at 6am. I felt the promises already being broken. I felt slightly nauseous from the cheap wine from the night before, and regret as I waited for the PATH train back to Manhattan. I texted Jordan. “How was your night?” I knew it was early, but I needed male attention.

“You’re up early beautiful.”

I sighed. I snapped a selfie and sent it to him. I still had my makeup on from the night before.


And as we exchanged texts during my commute home, our conversation soon progressed into a more sexual territory and this time I didn’t resist. When I got home, I pulled my shirt down, pushed my boobs together, and sent him another picture. He quickly replied.

“So hot. Send more.”

Before I knew it, I had taken my shirt off and was angling the camera to capture my cleavage in the best light. Each picture made me feel a little more powerful.

“Babe. You are so hot. Your body is amazing.”

This became my new routine. I would try and entice his attention with seductive photos. I craved his replies and found that I was turned on by the knowledge that I had this almost desperate power over him. I thought of the last session I had with Dr. Connorwitz.

“Do you think you are sexy?”
“Um..I don’t know. No. I don’t think so.”
“Why not? What’s wrong with you being sexy?”
“I don’t know. Nothing. I just wouldn’t use that word to describe myself.”
“Do you think the men you are date would describe you that way?”
“I don’t know.”
“I want to give you some homework. Sometime this week, take a look at yourself and say, “Wow you are really sexy.” Do something that makes you feel sexy. Can you do that?”

I never made another appointment with Dr. Connorwitz.

Uninhibited by his geographic distance, I started to experiment with my new found feeling of desire. I felt free to say things to him and confided in him my secrets. I knew he was jerking off to the pictures of me. I tested out what I thought might turn me on. He would describe what he wanted to do to me, and then the pictures turned into dirty texting, and then me watching him pleasure himself. And then one day I found myself holding an iPhone in one hand over my body and touching myself with him watching.

I most enjoyed post orgasm chatting with him. Bright, and thoughtful he asked questions and made observations that were welcome — albeit sometimes hard to hear. In my life, he filled something that was absent. A relationship that was just mine. It felt like a secret that I wanted to keep. In the back of my mind, I had a feeling that this new relationship was going to lead to trouble.

I tried to put out of my mind the day when he would tell me that he was no longer interested in me.

Our First Fight

I should be careful to use the pronoun “our”, and the noun “fight.” “Our” implies it involved two people, and “fight” implies a two-sided argument.

One morning, we had quick, demeaning phone sex. I was late for work, but he was persistent and I hated disappointing people — especially him. He mostly wanted to talk about having anal sex. After he finished, he seemed in a rush to start his day, and quickly hung up. I put it out of my mind, until he called me later that night and told me he was “actually in New York for the night.” It was almost 11pm. Why hadn’t he mentioned it all day? Why hadn’t he sent me a text on the 2 hour train ride?

I was annoyed.

How could he not take me seriously? I felt like a joke.

I replied, “Enjoy Tinder in Manhattan.”

He called me. I ignored the call. He called again. I answered.

“Are you mad at me?”
“What are you doing?”
“Just watching TV”
“I wish I reached out earlier. My hotel room is pretty nice.”
“I have an early morning.”
“Oh yea, me too. I definitely can’t see you. I have no time.”
“Ok, babe. Let’s talk tomorrow. Sweet dreams.”

The next day he was pretending nothing was different — sending me selfies of his new haircut and a dog he was thinking about adopting. I tried to ignore him, but I have a personality defect where I can’t ignore people. I drafted and redrafted what I thought would be the perfect text. Something that showed my disinterest — while at the same time enticing his interest.

“I had a nice time chatting with you this last month. If I’m in the “mood” I’ll reach out for sure — hope you find what you are looking for.”
He replied, “What?”
“What? I mean, that’s my current read.”
“Am I misinterpreting something? Like I told you, no one ever seems like that kind of guy.”
“Only interested in sex texting and dirty pictures.”

I sat at my desk contemplating the outcome I wanted. Why was he pretending like nothing had happened? I wanted him to feel badly, but did I really have the strength to stop talking to him? Historical evidence suggested otherwise.

Besides, I was enjoying the regular phone sex and found his attention to be a welcome distraction from the everyday heartache of my local dating life disasters.

I waited for his reply.

“I have been avoiding conflict ever since. I apologize”
“Since what?”
“Since Thursday when I was in New York.”
“OK. You could have just apologized.Instead I just read everything as you being over me.”

I watched him typing, the little dots moving in his iMessage. I wondered if I had ruined this for no reason. Was I even upset? Did I even want to see him when he was in New York, or did I just want him to want to see me?

“I’m Sorry.”

I let out the breath I didn’t realize I had been holding.

It wasn’t over yet.

Our First Meeting

Jordan picked me up at my apartment building at 7:00. I was nervous, but within minutes felt at ease. He had a handsome face, and was tall and I’m immediately attracted to his energy. His smile was the same from the pictures. One part kind, one part smirk. We drove to Katz’s to get deli sandwiches. At dinner, we chatted about life, and relationships. He offered his thoughts on dating and what I was looking for in a relationship with men. It felt strange to have someone who I thought I knew so little, know me so well. His demeanor made me feel safe in admitting that his assessment might be correct. I pointed to the sign above us that referenced the famous “When Harry Met Sally” fake orgasm scene. “Isn’t it weird that you’ve seen my finish before and we’ve never even met?” He blushed.

I was sure that despite our sexual text exchanges, we’d both decided to be behaved for the evening and keep our hands to ourselves. His advice on my dating life indicted his desire for a platonic night. I felt more at ease telling myself that. I liked Jordan, and the idea of being friends with him was appealing to me.

After dinner, we walked to a nearby bar. My favorite Jalapeno margaritas were no longer on the menu, but the bartender made me one, and then another. I wasn’t sure if we were flirting, or solidifying our non-sexual friendship. I wasn’t sure if I should stand up and put my body close to his, or tell him a story that would make him laugh. Or both. Jordan said, “I see us being friends for a long time.” When he touched my inner thigh though, I knew that if he made a move I’d be in trouble. I thought to myself to be cool and let him decide. I was feeling handsy from the tequila and didn’t want to make things awkward.

Things got more suggestive, and I thought to myself that he must be flirting with me. But I’ve been wrong before, and I’ve felt like a fool before. At this very bar before. I could feel myself getting nervous, and my cheeks felt warm. Smiling awkwardly, staring into my drink, trying to figure out what would happen next. We almost kissed, but didn’t. He backed away, or I backed away. But the hesitation was enough to make me feel uneasy. I leaned back on my barstool and took a big sip of my water. I thought, maybe if I drank the water fast enough I’d be more clear headed. But I couldn’t help myself. I leaned forward, “So what do you think — what should we do now?” He boomeranged the question back to me. Boldly, I replied. “Do you want to see my apartment.?” He smirked, understanding what I was asking. “Do you want me to see your apartment?” I asked if he was going to kiss me. And then he leaned in and did.

We drove back to my apartment and he went right into my bedroom. We had agreed to make out, but within minutes, I was renegotiating this in my head. Debating how far I could go without having any regrets. His hands were on my body, and then in my jeans. He put me on my stomach, and kneeled behind me. I enjoyed the feeling of him on top of me. I felt his hands between my thighs and him push his fingers inside of me. He put his hands on my neck while whispering into my ear that I wasn’t going to get to feel his cock. The months of anticipation was too much. I grabbed at his belt, and then started to unbutton his shirt. He was above me, kneeling, and gazed at my now exposed body. “I want to fuck you.” I reminded him of our plan — kissing-only — and we started making out again. He put his now hard cock inside of me.


He sensed my uneasiness, leaned back, put his hand on my cheek, and said “You’re OK, It’s OK.” We laid down next to each other and starting kissing again. Soon I found myself in the scenario I had described to him many times. Between his legs, his dick in my mouth. When he suggested sex, I resisted again. When he finished, we both agreed that we had done the right thing.

Lying in bed with him, I thought about our phone conversations, all the descriptions and details of what we’d do to each other given the chance. He was gentler than I expected, and having him in my bed was better than I had imagined, and I kept wondering if I’d regret not sleeping with him. I put my head on his chest and enjoyed the moment. We started chatting and began sharing secrets — the kind of secrets that are only shared between two people in bed. His are not mine to tell, and mine are ones I’ve never told.

I didn’t want him to leave my bed. I was enjoying the warmth of his company. He made me feel beautiful, sexy and interesting all at once. We started kissing again, and our hands wandered around one another’s body. I wasn’t sure I’d be able to keep my resolve this time. I asked if he’d put a condom on but he resisted. I was scared of what he’d think if I let him leave. So I obliged, and got on my hand and knees. I quieted the concerns swirling in my mind, and was on edge waiting to feel him inside me. Neither one of us said anything. I waited. I took a breath. And then, I felt him pushing into me.

“It’s already in all the way, babe.”
“Does that feel good?”

I wasn’t sure.

“Yes, baby. You feel so good.”

He lay down next to me, and held me in his arms. He gave me a soft kiss on the cheek. I loved the feeling of being wrapped in his arms and feeling him exhaling on my neck.

“Well that went from 0 to 60.”
“What do you mean?”
“We said we were just going to make out, and then…”

My voice trailed off.

“I know. It was amazing. How do you feel?”

I didn’t answer. I tried to playfully suggest that he say the night. It was already 4 in the morning. He was cross.

“Arielle, I have to go.”
“I know. I know.”

He got up to get dressed, and I followed him to the door and kissed him goodbye. After he left, I sat on the edge of my bed and started to cry.

Dear Jordan,

I can’t believe I fell for you. I am such an idiot. And worse, I can’t seem to control myself from texting you even when it’s clear you have lost any enthusiasm to hear from me. I send you nonsensical texts, a veiled ploy to initiate a conversation.

“25 things you can do with a can of tomato soup. Besides serve it. Read More”
“Didn’t you mention you liked tomato soup when we were at Katz’s?”
“Oh ya.”
“I mean kindof…Thanks.”

Your text replies are matter of fact. I can feel the disinterest and ignore it. You haven’t texted me first in weeks. You’ve stopped calling me. You’ve stopped asking me how my day was, or what I have planned for the weekend.

How soon after you had sex with me did you realize that you were going to stop speaking to me?

Or was it as soon as you picked me up that night? When you were waiting outside my apartment? When you finally saw me and realized my thighs seemed bigger and my chest seemed smaller than what you imagined? They say relationships are all about timing — was I a victim of bad timing, or some long tortured emotional game.

You were never my boyfriend. I know that. But for months, within minutes of my alarm, I’d reach for my phone and text you. Or respond to a text that you’d already sent. I’d send you pictures of my body, and watch you pleasure yourself. I’d listen intently while you described what you wanted to do to me. I’d put you on speaker phone while I brushed my hair, and put on my makeup and talk about my day. Doesn’t that count for anything? I guess not. I should have known you weren’t a nice person by the way you spoke to me. You wanted to use me like a toy for your pleasure. You said this to me. Why am I surprised that’s what happened? It’s my fault. I didn’t listen.

It’s not really my fault, but I’ll blame myself anyway. How stupid of me to think any of it meant something to you. You were charming, and cast a spell on me of feeling wanted. Made me feel special in a way that I needed, asked me intimate questions about my life, spoke to me like you cared, and complimented my body in a way that I craved. But that’s the fucked up part. Now, I feel worse. Used. I ignored all the signs of heartache. From the moment we first started talking.

“I’m in control of this friendship.” I asked you what you meant, but you brushed it off as a joke. At the bar, you leaned into kiss me, put your hand on my inner thigh, and then leaned out — “If I was going to hit on you, that would be my move.” I was in the middle of telling a story- and the train of thought evaporated from my mind. My insecurities had risen to the surface — waiting beneath my skin, anxious to be released — and all I could think was if you thought my inner thigh was too soft when you touched it.

You told me you were starting to see someone in Philadelphia and didn’t want to hurt me. I had sensed weeks earlier you starting to pull away from me.

Didn’t you know I’d beg for your attention when you rejected me?

Of course you did. And so, I found myself wanting to win your attention back on our date. Maybe- if you had a really great time you would realize that this non-relationship could somehow compare to whatever connection you’d made with whatever that girl’s name is in Philly. Obviously, I know her name. I always listen intently to the details of the personal life you reveal. But maybe, I could somehow convince you that I was deserving of your attention. I didn’t want to fail. I didn’t want to be rejected. I didn’t want you to not want me — to not want to make love to me — to not want to fuck me. I wanted to win. Even though I never win. Even though, I knew it was a bad idea. Even though I knew I couldn’t protect myself from your imminent disappearance. Even though I knew it was already destined to end the way that it has.

After two cocktails, I suggested we go back to my apartment. I was attracted to your demeanor, and how you made me feel. I wasn’t particularly attracted to you. When we went into my apartment, you went right into my bedroom and lied down on my bed. For a moment, my brain took the reigns, “Don’t you want to go to the couch?” trying to get us back on the kissing-only plan of action we had both agreed too. You replied, “I thought this is what you wanted.” I read your expectations. I took off my shoes at the end of the bed. I got on top of you and arched my back and moved slowly over your body, trying to make you feel good. You were rough with me, threw me on my stomach, put your hand on my neck, and pounded your fingers inside of me. I didn’t feel as good as I thought it would, but I wanted you to be happy. And I wanted you to like me.

We fooled around a little more, but I still wasn’t sure if you found me attractive. I wasn’t sure if after hearing all your fantasies, I was enough. I didn’t want you to be disappointed. So I begged you to fuck me. I knew it was a bad idea. And I knew, I’d regret it. Because I was having sex with someone who I knew wasn’t going to date me, and I wasn’t even sure you wanted to be my friend. I tried to follow your rhythm, pushing myself back into you. When you asked me where to finish, I got anxious. I wasn’t sure what you wanted. I replied, “I don’t know.” I could feel my face getting flushed. I felt out of control. And then I came and I wasn’t sure if you did. In my effort to please you, I now felt like I had let you down.

I’m so sorry.

The Morning After

“Just wanted to say Good Morning! Sorry I didn’t stay over. Had to get back to my parents house. It was great finally meeting you. Last night was fun…even though I lost my credit card. 😬😬 ”
“Oh no! Did you leave it at the bar?”
“No worries. 😃 ”
“I think I have the manager at the bar’s phone number from when I used to be cool. I can call there and see if they have it.”
“OK. But really, no worries if its any trouble. It’s no big deal.”

I would spend the next few hours emailing, calling, and following up with any contact I had from the bar to locate his credit card. Once I confirmed they had it, I texted him again.

“They have it! When do you go back to Philly?”
“Wow! Thanks! Tomorrow morning. I’m not sure I’ll have time to come back into the city. Do you think they’d mail it to me?”
“I can go get it!”

This seemed like a good idea. Maybe a reason he’d want to see me again. I cancelled my plans after work so I could go get his credit card and kept my evening free in case he wanted to drive in to see me again.

“Mission Accomplished! I have your credit card. Let me know if you want to come grab it before you leave, or where I should mail it!”
“Do you mind mailing it to me? I’ll email me your address. I will Venmo you any shipping charges.”
“Of course!”

Three days later, and I still hadn’t heard from him. I know he got the package, because I had paid for FedEx Overnight Shipping with a signature required on delivery.

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