Brief Encounters with Dating in New York City

I’ve toyed with the idea of blogging about my encounters with dating in New York City for some time now. I usually reserve the post-date scoop for my sister, my girlfriends and sometimes my guy friends because I think they enjoy having a good laugh at my expense. Alas, I decided it was time to reveal snippets of some of the dates I’ve been on in the not so distant past.

Now, you may be wondering Jana, you’re such a catch: pretty, smart, witty, successful. Surely you don’t have trouble meeting guys. (I know, I know. Stop it! You’re making me blush.) I wish I could say that it’s so incredibly easy, in a city of millions, to meet an eligible bachelor.

I’ve put together some reasonable theories as to why I’m currently on the market. (Imagine I’m saying these in my best Mindy Kaling impression. I’m reading her book Is Everyone Hanging Out Without Me? and it’s laugh-out-loud-on-the-train-like-a-weirdo hi-larious. Now her voice is constantly stuck in my head.)

  • I’m just so insanely gorgeous guys don’t have the guts to approach me because they’re afraid of rejection.
  • I’m just so insanely gorgeous guys automatically think I’m unavailable.
  • I’m always surrounded by guys (who are my friends, duh) so other guys just assume I’m dating one of them.
  • I’m  obviously the perfect package, and guys know that when they meet me they’re in for the long haul. There’s simply no escaping my charm and good looks.

Jokes aside, out of all of the potential partners I’ve met since I started dating, there was a total of two guys who I considered dateable — and one didn’t even live here. Each one possessed the makings of what I’d consider relationship material, but I was sorely mistaken. They both flaked and disappeared. Their loss.

So let’s get to those dating stories, shall we? Allow me to preface this section by admitting to joining a dating site at one point during this past year. It’s really not that shocking a revelation because there are so, so many people doing the online dating thing. I mean, Martha Stewart is legit on (Publicity stunt or celeb endorsement? Who knows?).

Anyway, so yes, one random day I joined a dating site and found myself filling out an online profile with all of the charm and wit I could muster. I wanted to find out for myself what it was like. And let me tell you, the messages I received were nothing short of entertaining. I took screenshots of nearly every message I ever received and tucked them into a folder on my MacBook to revisit at a later date.

What you are about to read are snippets from a “diary” that I’ve kept, which recounts some of the dates I’ve been on, not all set up via the dating site, mind you. All names have been changed to protect the poor souls who I will likely make fun of for the rest of eternity.

Blake: On a cool, rainy night, we met at Nights and Weekends. He was seated near the door. He stood up to say hello and to hug me. To my surprise, he was much shorter than I expected. I was wearing heels. (This is the part where I tell you that I cannot possibly bring myself to look past a man’s shortcomings — pun intended? — and need to date someone who is taller than me. That and feminine hands — they absolutely creep me out. Manly hands, please.) I thought we were getting along quite well so the end of the night came as bit of a surprise. When I returned from the ladies room, Blake quickly said something along the lines of “Hey, so I just realized what time it was. I have to wake up early tomorrow. Do you mind if we leave?” Well, I wasn’t going to argue. I gathered my purse, threw on my jacket and we walked outside into the dreary, damp night. We awkwardly hugged and walked in opposite directions. I never heard from him again.

James: Our happy hour date was quickly approaching, and I was still deciding on an outfit. I’ve found this to be a common problem. Choosing a first date outfit is incredibly difficult. James was pretty easily spottable considering his long blonde locks. He was seated in the back near the patio door, which made for some decent people-watching. Conversation was touch and go. He seemed shy, and I took over the talking because I couldn’t bear awkward silences. He contributed here and there. I began to hate the sound of my voice. In my mind I was thinking please just say something! After a couple of beers, I used my planned escape excuse (a good idea to have one in the event that you hate your date) and suggested we part ways. (Note: I didn’t hate this date, but I didn’t want to spend the rest of the night with him.)

James date two: James invited me to a show at The Bowery Electric. In between making plans and date night, he texted me often with annoying messages like “I want to kiss you” and “I can’t wait to see you” and “I can’t wait for Janaday” etc. I responded vaguely and tried to maintain a casual interaction. Date night arrived and, amazingly, I had a stellar pre-planned outfit. James suggested meeting before the show for dinner at Rabbithole in Williamsburg. It was a cute place serving a variety of interesting hipster fare. I chose the quinoa and artichoke salad, which was delicious but small. Since I was still hungry, I grabbed the dessert menu (which was misspelled “desert” in one spot and I contemplated telling our waitress) and opted for the cheesecake. While we enjoyed casual dinner conversation, that I pretty much dominated…again…our waitress overheard me mention something about Buddakan in Philadelphia. As it would turn out, she used to live in my hometown (Lehigh Valley) and worked at Vegan Treats. Small world. After the show, I found myself back in James’s neighborhood and felt majorly awkward. I could tell he wanted me to come over but I didn’t want to stay the night. I told him I was going to walk home. He told me I should stay and that he would sleep on the couch. No, thank you. Buh-bye. I walked home in the rain at about 1 a.m. Afterward, James continued to send me those cutesy text messages that I hated. One day I was honest and told him it was too much too soon and that I wasn’t looking for anything super serious. He never texted me again.

Derrick: Thankfully I arrived first — or so I thought. I chose a table along the back wall of the bar. Derrick was apparently outside on a conference call. I must have breezed right by him as I walked in. Immediately after we greeted one another, his phone rang and he dashed outside to take the call. I couldn’t help but think oh great, one of those guys. He kept his phone in his pocket the rest of the night. When he came back in, my gaydar went off. Maybe he was metro or maybe I’m just used to dating dudes. We ordered a couple of small plates and some drinks. The conversation came organically and easily. Then he told me about the crazy girl he dated for about four months, and a red flag appeared in the back of my mind (I’d known this dude for an hour at best). Not sure about this guy and his dating history. It must have been my lucky night because his dating history quickly became dating present when we strolled to another bar for another drink. We settled down into a cozy booth and he ordered our drinks. All of a sudden, an unexplainable awkwardness hovered over our heads and soon enough I understood why. He spotted a girl who he had gone out with — the week prior. Derrick and I attempted to redeem the night with more stories when we were interrupted by said girl who requested his presence in the back of the bar. He left me sitting there alone for about 15 minutes while they hashed out some unfinished business (that he did not share with me when he returned). In hindsight, I should have just left. There was no second date. 

Christopher: Even before I left my apartment, I dreaded this date. I honestly don’t even know why I made plans in the first place. I dreaded the date because I wasn’t in the mood for a date. I dragged my feet getting ready and threw on a go-to dress because I didn’t care. Actually, I tried not to care, but, let’s be honest, I always care about my appearance. Well, he was just as I expected — only worse. Christopher and I pretty much had the bar to ourselves for the first hour. I was half paying attention to our conversation. I just wasn’t invested and I didn’t care. I was absolutely horrified when it happened the first time. But then it kept happening. Again. And again. And again. He kept scratching his junk while we were talking. I mean…seriously?! I wanted to die. He didn’t even try to be discreet about it. I cannot make these stories up. At some point, a handful of people filtered in, and a DJ started playing this weird arty Brooklyn noise (I can’t even call it music). Imagine the music you’d listen to while on acid. That’s what this was. (I’m just guessing this is what music might sound like on acid. I’ve never done it.) So yeah. We left the bar, and he tried to go in for a kiss, which I dodged by submitting to a second awkward hug. I hurried away and never looked back.

Brad: I met Brad at Beauty & Essex. He first caught my eye outside while I waited for my friends to arrive. At around midnight we finally connected when he approached me to chat. He had a perfect smile and a mouth full of perfect teeth. His smile and teeth definitely gave my smile and teeth a run for their money. Before parting ways for the night we exchanged numbers and he texted the next day. (Major happy face!) He planned our first date, and we met several days later at an authentic Japanese sake bar in the East Village. It was this tiny, obscure basement with graffiti all over the walls. I was infinitely impressed with his ability to actually plan a date. We talked nonstop and all signs pointed to “yes, proceed.” We walked hand-in-hand as he led me to his favorite pizza shop and we kissed under a streetlight on St. Mark’s Place. I later hopped on the L with a stupid grin slapped across my face. Because I wanted to tread waters carefully so as not to scare him away, I waited a day to contact him when he didn’t reach out himself. A little small talk and that was that. Never heard from him again. The only conclusion I could come up with was that he already had a girlfriend who was away visiting her family and even though he’s bored and wants to break up with her, he can’t, so he disappeared. That, or he’s a stellar actor. 

A few things I’ve learned about dating in New York City thus far:

  • I am the sanest/coolest girl these guys have ever taken out on a date. I know this because I’m often told this in so many words or less.
  • Guys don’t like to or don’t want to pick up the check. HE asked me out on a date. HE should try to impress me by paying the bill. Oftentimes, I’m left reluctantly offering to pay my half. Just be assertive and pick up the check because you are a man and that’s what men do on first dates. On or around the fifth date, I’ll happily contribute or pick up the tab.
  • Guys always take the bench seat leaving me with the stupid chair. Hello! Let the lady sit in the comfier seat — always.
  • Most guys forget to do these simple yet critical chivalrous gestures, including, but not limited to: opening doors, letting me walk in front of him, paying the bill (as stated above), pulling out my chair, complimenting me…
  • Guys don’t like to or don’t want to plan the date. This one truly boggles my mind. HE asked me out on a date. HE should try to impress me by planning the time and place. Just tell me where to be and when. It’s that simple.

And that, my friends, is why I remain single. Lately I’ve been envisioning myself clumsily bumping into the gorgeous man of my dreams, spilling something on him, apologizing profusely and living happily ever after. Instead, I’ll probably get stuck suffering through another ball scratcher and obsessive cutesy texter. I’m sure you can imagine my excitement as I type this. Until next time…

10 thoughts on “Brief Encounters with Dating in New York City

  1. So, so, so very entertaining as always! You could write a book about these crazies. I wanted to keep reading and was sad when it ended.

    P.S. – none of these guys deserved you, clearly. All of your alleged “joking” insights were 100% correct! You’re the total package. Any day now you will accidentally spill something on Mr. Perfect, lock eyes and live happily ever after. I know it!


    1. Aw shucks! You’re too kind, Amanda! When I do spill something on Mr. Perfect, you’ll be the first to know. By the way, I wanted to keep writing and writing and writing, as I’m sure you could have guessed. Then I’d have to entice people to spend an hour on my blog reading my novella. xo


  2. jana-
    So funny. I agree you are all of the above. Thank god our first business meeting went so much better. On a side note, I was spring cleaning and going through about 75 old magazines when I came across an October 2007 issue of Style. May have been your first appearance. If you want for a keepsake, let me know. If not, the circular file. Take care.


  3. Jana, you need to “not try so hard” you are an awesome woman and romance will come when you least expect it. I just can’t wait to read about that one as it happens to you.. Remember, the best comes to those who wait for it!


    1. What’s funny is I usually date because I get bored, not necessarily because I’m looking for love. I’m perfectly happy being single. When I do meet an awesome guy, it’s going to make for some great blog fodder. I hope he’s prepared!


      1. Oh, I know, it’s just another experience to chalk up. Love you Jana and keep on writing these awesome blogs. I read every one of them.


  4. Bad dates = great stories. I feel like we talk more about the bad dates than we do the good ones! Although frustrating at times, they’re what make dating & life interesting (and the good dates much more special).


    1. So, so true! It’s easy to talk about the bad ones. I’m starting to think that when I gush about a good date, I totally jinx it. I’m thankful for the bad dates. They help me confirm what I don’t want in a future partner and make for awesome blog posts.


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