Laid in Manhattan – The True Story of My One-Night-Stand from Hell

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When I graduated college, I was pretty certain that it would just be a matter of time before I met some amazing guy, got married, and started a family. After all, I was in my early 20’s, had escaped 4 years of undergrad without gaining any weight, and was working in Manhattan for a brag-worthy company (making pennies, but still)! And since I have zero ability to live in the moment, along with a glass-half-empty outlook on life, it was not surprising that I began to preemptively stress over what experiences I might not have before I ended up marrying the last man I would ever sleep with. Not that I was totally inexperienced or a prude, but there were definitely some things that I had yet to have done, sexually speaking. Contemplating a future with one, and only one sexual partner, prompted me to create my own little bucket list – a sexual bucket list, if you will, that I decided I would have to complete before my upcoming matrimony to my then unidentified future husband.

My list went like this:

  • Have a one-night-stand with a total stranger
  • Have sex with a significantly older man
  • Have sex with someone remotely famous

Yeah, that was the whole list. I figured anything else sexually explorative could be done with the future husband except for these three items, assuming that my future husband didn’t turn out to be a 40-year-old, D-list actor that I slept with the first time I met him.

Of the three, for whatever reason, the one-night-stand seemed really appealing to me. Perhaps I had seen too many Lifetime movies or episodes of Melrose Place, but for whatever reason, the thought of one night of unbridled passion with a super hot stranger was a total turn on. I would picture it in my head and it always looked the same: ridiculously gorgeous man and I lock eyes in a bar/on the train/ at Starbucks / at a party / on the sidewalk, there is an unspoken, telepathic understanding that we both find each other extremely attractive and must have each other at that exact moment in time. We end up in his apartment/my apartment / a hotel / wherever and proceed to tear each other’s clothes off while knocking over lamps, destroying furniture, and having sex everywhere except for the actual bed, culminating in 37 orgasms, 2 cigarettes, and a walk of total un-shame 1-2 hours later.

That was the dream.

The reality however, was, how shall I put this, remarkably different, in that none of those things actually happened except for the sex, and that’s being generous.

At the time I met Jon, I had been working for a few months in the marketing department for a large global company. As part of my job, I would often have to communicate with sales managers from some of our other locations. One of my contacts called me one day to let me know that someone from one of our affiliate companies based in Los Angeles would be coming to New York and he thought I should sit down and meet with him to discuss some potential marketing ideas. First of all, I didn’t have a fucking clue what an affiliate was, who this person was who was coming to meet with me, or what on earth I was going to talk to him about. Clearly I had no clue what I was doing at my job, period. But I played it cool and told my contact that it sounded fantastic. Fake it till you make it, right?

The day of the meeting arrived and I went to meet Jon in the lobby. I actually think that my jaw literally dropped the first time I laid eyes on him. Like out of a movie, I found myself tongue-tied and physically crippled by the site of this beautiful specimen of a man. If I had no idea what I was going to say before meeting Jon, I sure as fuck had no idea at this point if I would even be able to speak anything that even sounded remotely like English. Luckily, along with the looks of a Greek God, Jon also had a friendly, outgoing personality so he began chatting away as I guided him over to a booth in our cafe.

Armed with a notepad, I sat across from Jon and waited. He took out his papers, folded his hands in front of him, turned to me and smiled. His piercing blue eyes looked at me inquisitively. I could feel my face getting hot, and I am not a girl who blushes, but sitting across from Jon was literally making me all hot and bothered. I vaguely remember him taking the lead and explaining what his company does and how they work with our company re: marketing. I’m sure that Jon was able to tell within two minutes that I had zero clue what he was saying, especially considering I couldn’t stop staring at his lips and imagining what they would feel like against mine.

Jon stopped after a few minutes and smiled at me. “Forget work,” he suggested, “tell me about you.” For the next hour or so, Jon and I talked about everything, where we went to college, what we did for fun, etc. He casually inquired about a boyfriend/husband and seemed relieved when I said I didn’t have either. He was single as well (how on earth, I wondered?). It became quickly apparent that the attraction was mutual, as we were acting like giddy teenagers, laughing at everything the other said, smiling non-stop, and dropping not so subtle hints to the fact. Before I knew it, 2 hours had passed. I looked down at my notepad and saw that I had written Jon’s name and company, a few words regarding the “business” we had discussed, and then had filled with rest of the page with a lot of doodled hearts. Jon looked at my paper and smiled.

I walked him out. We lingered. He told me that it was really nice meeting me and suggested we keep in touch, and mentioned that he would probably be back in NY soon and that we should set up another meeting then. I agreed and we unprofessionally hugged a few seconds too long, and kissed on the cheek goodbye.

Jon emailed me within the hour to tell me how great it was to meet me and to thank me for the productive meeting (he added a smiley face). He let me know that he hoped to see me again on his next visit. I responded and agreed that I thought we had gotten a great deal accomplished and that I would love to continue our meeting the next time.

For the next two months, Jon and I emailed back and forth nearly every day. The emails had now become strictly personal. Nothing inappropriate, but definitely flirty. There was no denying that we were on the same page as far as our interest in one another, so I was thrilled when one day I got an email from Jon telling me that he would be in town the following week and that he had set up a late meeting with my boss that Thursday.

“Why don’t we go for dinner after my meeting?” he suggested. I told him that I would love to and that I was looking forward to seeing him again.

And then my brain went there. Ok, this guy is so gorgeous that the site of him takes my breath away. However, he lives in L.A. So realistically, this is never going to happen. But – I obviously have to sleep with him and it’s obvious that he wants to sleep with me. This is the perfect chance for me to finally have my one-night-stand! I had already been mentally ripping his clothes off in my head since the day that we met, so I  knew how amazing the sex between us would be. It was settled then. I would be having sex on Thursday night and it was going to be incredible!

Jon and I didn’t make and detailed plans, so I wore something nice, but casual to work that day and waited for him to arrive. The sight of his beauty as he entered the office just reaffirmed my plans for him later. After his meeting with my boss, he stopped by my desk to say hi and to make sure we were still on for that night. He had just arrived in N.Y. that day, so he didn’t have anything concrete planned, but he suggested we play it by ear. He asked if I minded meeting him at his hotel and going out somewhere over there. This was going to be too easy!

After work I cabbed it over to his hotel and knocked on the door to his room. Jon opened the door with a huge grin and invited me in with a warm hug. I walked into his suite and stood there awkwardly.

Should I just jump his bones now? How exactly is this supposed to work? Do I wait for him to initiate? In my mind, he initiates it, right? No, in my mind we both look at each other and grab each other at the exact same time. This all seemed so much less complicated in my head. Fuck…

“Want to go grab something to eat?” His voice cut through my panic attack. Yes! This will give me time to sort this whole thing out. Jon ended up suggesting we grab a slice of pizza (for a guy with an expense account who definitely is into me, I must admit he lost a few points here. Pizza, really? My fantasy of how tonight was going to go had definitely involved a sit down dinner at an upscale restaurant. But whatever – he’s so pretty…). After pizza Jon asked if I wanted to go ice skating at Rockefeller Center. Jesus fucking Christ. Ok, I’m starting to get the impression that this is going to be a long night and apparently I am going to actually have to work for this. Again, not quite what I’d had in mind! Ice skating in Manhattan is perhaps one of the most touristy things you can do, but again, he’s pretty, I want to bang him, so I agree.

Good thing I don’t live in Orlando or I’d be taking him on Magic Fucking Mountain!

After ice-skating, during which we held hands (aww), he suggests we go back to his hotel and have drinks at the bar. Yes, finally! It had been a long night and as we approached his hotel I began to get nervous again. How the fuck was I supposed to make this happen? I’ve never planned sex before, not like this anyhow. My solution – drink a lot! We sit at the bar, and after a couple of drinks I’m getting loose. Talk turns to sex. To be honest, I can’t remember what exactly was spoken about, but at some point I know that he brought up porn. I believe he asked me if I was into it. I think that I told him that it’s not really my thing, but that I’m not opposed to watching it with a guy that I’m with if it’s his thing. Another drink later and Jon suggests we take the party upstairs since the bar scene is starting to die down.

As we ride the elevator up to his room I know what is about to happen. I am eagerly awaiting walking into his room, the door shutting behind us, and the sexcapade finally getting started.

We enter his room. The door closes. He excuses himself to the bathroom.

Alrighty then.

I take off my coat and sit down in one of the chairs in the living room. Jon comes out of the bathroom and walks towards me with a smile. Here we go!! He walks past me towards the tv and grabs the remote control.

Ummm.

I sit there, nervously stirring my drink, confused. Jon continues to scroll through the guide until he finds what he’s looking for.

Oh, holy mother of God. No!!! Don’t do it!!!! Holy fuck. He did it.

Jon put on a porno.

Let me tell you, there is nothing more awkward than sitting in a room while a near stranger puts on a 70’s porno without discussing it with you first. The silence was deafening (except, of course, for the grunts and groans coming from the tv). I wanted to die. A part of me wanted to run. But no, I was still determined to do this. So what if it’s not exactly going how I imagined? No, porn had not been in my fantasy… but perhaps I could get past that.

If only he would stop staring at the screen and peeking over at me. Ugh.

Finally I’ve had enough. Clearly I will have to make this happen myself because this guy has maybe the worst game I’ve ever seen. I get up and seductively walk towards him and gently take the remote from his hand. I turn off the tv and turn back towards him and begin kissing him.

We stand there kissing for a few minutes. Finally we stop and he says, “I’ve been wanting to do that all night.” He takes my hand and leads me towards the bedroom. More kissing, and kissing, and kissing. Finally, I just start to take off his clothes. He stops me. Are you sure, he asks? Is he really going to make me have this conversation??  I’m pretty sure I tell him to shut the fuck up and continue to try to remove his clothes. He stops me again. He doesn’t have a condom.

Awesome.

My thoughts at this moment: A) We are not supposed to talk about the condom, it is just supposed to magically appear. Doesn’t he know this? B) How does he not have a condom? What exactly was he thinking was going to happen tonight – ice-skating and platonic porn watching??

He will be right back, he says. He gets dressed and races out of the door. What the fuck am I doing, I wonder? This night has been one disaster after another, and even though I know that I should just cut my losses, it’s too late – I’m too committed. Plus, at this point, it’s the middle of the night, and I wouldn’t feel comfortable taking the train back home since I didn’t live in Manhattan. I quickly called my roommate, who also worked with me, and asked her to meet me before work in the morning with some clean clothes for me.

Jon comes back with a bag. Condoms and a toothbrush for me. What a guy. He hops into bed and we start from where we left off. This has been a fucking process at this point, so I am banking on this being worth it. Jon, as it turns out, is a moaner. He moans when he kisses me, moans when HE touches ME, he just moans. A lot. It’s kind of disturbing. We are finally naked and, it’s hard to explain, but it’s as if he isn’t quite sure what to do with me. He hesitantly goes for my boobs, but looks at me as if to see if it’s ok that he touches me there. I kind of give an annoyed quick nod of approval (kill myself) and he touches me. Then he moans. Fuck my life.

He starts to go down on me. Ok, maybe things are starting to look up a bit. Three seconds later, after a flick of his tongue (and a fucking moan), he’s back up and reaching for the condoms. Seriously? At this point a) it has become evident why he is single, and b) I am wondering if mine is the first vagina he has ever made contact with, and c) I just want this to end.

Luckily, I don’t have to wait that long. Jon get’s on top of me, missionary style, and we being to have sex. Before I can count to 10, Jon has climaxed (loudly), and is gasping for breath. I look over his shoulder to see where the hidden camera is because clearly this is a joke. He rolls off of me and leans over to kiss me. “I’m sorry, I was just so turned on by you. That was amazing!” I stare at him dumbfounded. He asks if I’m ok, as if to imply that maybe I’m regretting sleeping with him, or perhaps to make sure that I’m not sore (Bahahaha). Well, I am regretting it, but not for the reason he thinks.

Two minutes later, Jon is asleep next to me, snoring, with his arm wrapped around me like a vice.

Well, that did not go quite the way I had hoped. No animalistic sex (unless you count the people in the porn – ugh, the porn!! Cringing), no broken lamps, torn clothing. Nothing. Two minutes of missionary style and a sweaty arm pinning me to the bed. And I was forced to ice-skate for fuck’s sake!

Worst. Night. Ever.

The next morning I woke up feeling disgusted. Jon was in the shower, so I snuck into the other bathroom to take a shower myself and to see if I could wash the humiliation and shame off of me. He called in to check on me when he got out of the bathroom and I told him I was in a big rush because I had to meet my roommate to get my shit. No thanks, don’t need coffee!

At the speed of light, I re-dressed in my clothes from the night before and prepared to do the subway ride of shame. Jon tried to be sweet, telling me what a great night he had, how it was unexpected (wtf?) but wonderful. How I am so beautiful and he want’s to see me again when he comes back, hopefully in a few weeks. I plaster a smile on my face and nod. He tries for a long kiss but I cut it short and run for the elevator, yelling behind me that I’m running late. I race out of the hotel and towards the subway.

It isn’t until I am sitting on the subway, heading towards my office, that I realize I’m crying.

I feel awful. I feel like a slut. I feel ashamed, mortified, dirty. What was I thinking? I am not a one-night-stand kind of girl. Why did I just sleep with a fucking stranger? I’m upset and I’m mad at myself. And I’m mad at him for being the lousiest fucking lay!!

I get to work (thank goodness my friend came through with the clothes) and check my email. Jon has already written to me by the time I get to my office. “Last night was…amazing.” He can’t be serious. I’m seething. I write him back something quick about how it was nice to see him and I had fun. I secretly hope to never hear from him or see him again.

The next few weeks I slowly begin to come to my senses. I realized a few things about myself. First, I take sex a little more seriously than I thought I did. Second, I was indeed ashamed of myself, but I was more upset that the whole thing was a disaster. I recognized that if it had gone how I had fantasized that it would, I probably wouldn’t have cried afterwards and hated myself quite as much – I was probably more disappointed than anything. Third, yes Jon was the worst in bed, poor thing, but he was not a bad guy. He was actually very nice. He just had zero skills, and it was unfair for me to aim all of my anger at him (I had been ignoring or barely responding to his emails afterwards). And finally, the bucket list thing was stupid and I was over it. I’d had amazing, mind-blowing, steamy-hot sex before, and I would have it again. But planning for it had been my downfall.

Jon came into town a few months later and wanted to see me. At this point I felt guilty for taking out all of my issues on him, so I agreed to meet him out for a drink with another couple. He invited me back to his hotel room, but I declined. I might have been over it, but I wasn’t fucking crazy. I saw him a few months later when I was in L.A. for a convention. He mentioned getting together, but it didn’t work out because I ended up being “busy.” So, in fairness to Jon, he didn’t have to be a one-night-stand, because I had more opportunities to sleep with him, and it’s possible (and I hope for his sake) that he may have totally redeemed himself if I had agreed to it. But Jon was meant to be my one-night-stand guy – perhaps only to teach me that I am not a one-night stand girl.

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28 thoughts on “Laid in Manhattan – The True Story of My One-Night-Stand from Hell

  1. Oh wow. That sucks! Although, you could have taken those other times to teach him a thing or two! 😉 But I agree, I am not a one night stand kind of gal either. I just don’t think it’s in our make up. 🙂

    1. Oh honey, there was just way too much to teach! Tired just thinking about it. But yes, turns out I’m not cut out for that sort of thing…unless that sort of thing had turned out exactly how I had hoped it would – perhaps then I would be singing a different tune…?

  2. I’m not exaggerating when I say that I was at the edge of my seat saying holy shit the entire time I read this. First of all, this was an amazing read. Well written, funny, and approachable. I’m going to think about this next time I “convince myself” that I could handle a one night stand. Incredible article.

    1. 1) I love you 2) If you ever decide to have a one night stand, test drive by making out first. I left out the part about him being a terrible kisser because I was starting to feel bad for the poor guy. That probably should have clued me in. Oh, and don’t sleep with anyone who suggests ice-skating. xoxo

  3. I love this story for so many reasons but you tell it so great! I’m sorry it wasn’t what you had hoped for but at least you learned a few things in the process! I really enjoyed your writing style, I will be back for more! xo

    1. Thank you so much! I definitely learned one thing – never sleep with a guy who asks you to ice-skate 🙂

  4. Omg!!!!! Loved this!!! Love how you put a funny spin on such a situation lol…. I think all of us put so much hype on really anything in life and most of the time things just don’t live up.

    1. Thanks so much!! Yeah, most of the time the fantasy ends up being way better than the reality unfortunately 🙁

  5. I love the honesty, humor and realism in this post.

    We often build things up in our heads so much that the reality cannot hold a candle. Then, of course, TV and media often romanticize the heck out of these situations and there we have it.

    Thanks for the great post. I will surely be returning.

    1. Thanks so much! Yes, in this case the reality was on the other side of the spectrum, that’s for sure. Definitely too many movies! Lesson learned!!

  6. Just came across your blog and I absolutely love you honesty! Also, you’re an awesome writer, this feels like something from The New Yorker. I wish I had your balls… get it girl!

    1. Considering I’ve been doing this whole blogging thing for less than 5 months, that is a huge compliment, so thank you! If only I had the time to really promote it – too bad for full times jobs!! I hope I can continue to keep you entertained. Grabbing my balls now 🙂

  7. When you wrote “ice skating and platonic porn watching” I freaking died! My 3 yo came in and asked me if I was okay. Sorry you had such an awful experience but I’m so glad you learned something about yourself in the process. We grow far more from our failures than our successes. Head up, girl!

    1. Haha, I’m glad to hear that I made you laugh! Lousy sexual experiences are only worth having if you can make other people laugh by sharing them – at least that’s my theory. Thanks for the feedback!!

  8. I love everything about this. I, too, gave myself a checklist of men to “date” after college. I had been in a long-term relationship with an athlete that was a horrible decision from the start (I was 17), decided to date a touring musician (WHY!) and then an older man. I don’t even know what I was thinking.

    1. Thank you so much! Yeah, not quite sure why a sexual bucket list ever sounded like a good idea to me. A touring musician!!? Girl, you must have some stories of your own!

  9. Well, what a story. I had a grin throughout reading it. I love your language. It makes it seem like you are sitting there telling your story.
    All the best !!

    1. Thank you so much! That’s the feel that I am going for so I am glad to know that it’s translating! Thanks for the encouragement 🙂

  10. Why the fuckity fuck would you ever make time for a doosh who doesn’t know his way around Vagina-Ville?!

    BUH BYE.

    While I knew I was going to marry my fiance the first time I laid eyes on him… The first time he ever went down on me. DONE AND DONE. I may have yelped I DO?? No witnesses were around though, so I guess that doesn’t mean we’re married yet.

    1. Lmao – well to be fair, I didn’t know that he didn’t know his way around Vaginaville (I may have to steal that from you) until it was waaaaay tooo late 🙁 That was obviously the least of his problems though. Sounds like you got yourself a good one, lucky girl! XO

  11. I sometimes miss looking younger but I definitely don’t miss the sex from back then. It gets better, trust me–you may have already found this out. It’s hardly ever in one-night-stands and I never did the friends-with-benefits thing but good sex without commitment is out there. Rare, but it’s there. I guess you just have to hope you don’t get hurt trying to find it. I didn’t know feeling slutty was still a thing and it makes me a little sad. Don’t tell me all that work we did in the seventies was all for nothing…All the bad sex and teaching sweaty boys with raggedy fingernails and the sneaking, and yes, all those trips to the confessional on Sunday. This is a fun article and it takes me back a few (many) years. Marriage is boring but the sex is good. 🙂

    1. I don’t think that the slut thing is still a thing, at least not beyond high school. It’s probably more self-imposed more than anything. Basically I was feeling sorry for myself.

      I’ve had good sex without commitment but it always clouds my judgement and makes me think that I want more, even if the guy is a total tool. Thus my continued search for my unicorn 🙂

  12. You should write for a women’s magazine. You are brilliant at capturing these moments! (I’m just sorry this one particular story wasn’t quite the one you’d probably rather be telling.)

    1. Wow, thank you so much! That’s such a nice compliment! I don’t mind telling the story anymore – it’s actually quite amusing to me now 🙂

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