Playing The Dating Game : Episode 1


To give you a little back story, my best friend Jess & I became single around the same time last year after both ending long term relationships. Being each other’s therapists, we decided we needed time to be single and focus on ourselves for the first time in a long time, but that didn’t mean we weren’t going to have some fun!  We decided to post a couple of our crazy dating stories, the kinds of stories we tell each other over cocktails and laugh hysterically! If you guys like it, let me know because there’s more where that came from!  


I met Bernard on the street, crazy I know, because who meets someone on the street that they actually want to see again.  Anyway, we talked briefly, I gave him my number and we went our separate ways. Shortly thereafter, he asked me out for drinks during the week and I obliged. Having had a few drinks before our random street meeting, I couldn’t really remember what he looked like, but when I saw him I was pleasantly surprised. That’s when things got very interesting. It had been ten minutes into the date, and three sips into the $5 PBR he bought me, when he said, “Let’s just forget this and go to my apartment.” I responded with “what are we going to do there?”, already knowing there was no chance in hell I was going there, but still curious as to what his response would be. That’s when he came out with, “I’ve already felt your aura on the street and that’s what initially attracted me to you. I want to take you back to my apartment and intertwine my soul with yours.” I had a smile on my face, but not because I was interested in intertwining my soul with his, but because I couldn’t wait to tell Jess what this character just said to me. I felt like I was in a movie but I couldn’t tell whether it was a romantic comedy or a horror flick. I then replied with, “I’m going to leave now BY MYSELF, and if I turn around and look over my shoulder you better not be following me.” To my surprise, he started begging me to stay and at least finish my $5 beer. He also decided to take a completely different approach in trying to get me to his apartment. His final words to me were, “I want to show you how I arrange my trinkets on my windowsill in a way that’s pleasing to me.” Needless to say, I did not finish that beer.



So it’s actually happening. I am single for the first time in 9 years and I am BORED. It’s just me, sitting in my bed with my dog cuddled next to me and I am flipping through the channels. What to do? I decided to grab my phone and text Daniel. He was an investment banker who I met in an elevator when I was heading into a meeting. I texted him with a simple, “I am free tonight.” I knew he would jump at the chance to take me out because he had been nonstop texting and calling since the moment we met. He told me to meet him at Carbone. After getting there I realized he was even more handsome than I remembered. He was at least 6’2 with dark brown hair and big brown eyes. He definitely worked out a lot because his chest and arms were looking amazing in the button down he was wearing. I usually don’t date the “button down guy”. The man I usually go for wears a tee shirt with jeans and a retro pair of Jordan’s. He was already at the table when I walked in. He helped me with my chair when I sat down. “I couldn’t help but to notice the shoes you have on. Are those Louboutin?” I thought to myself, “that was different.” He didn’t even say hello yet and instead he is asking me about my shoes. “Uhm yeah. I have a shoe addiction and Louboutins are one of my favorite brands. How are you handsome?”  I wanted to act as normal as possible even though that comment threw me off. Maybe he is just nervous I thought to myself. “I am great and you look absolutely gorgeous.” We started looking over the menu and making small talk. I ordered a dirty martini and he ordered an aged scotch, he grabbed my hand and smiled at me and said, “Do those shoes hurt your feet?” Did he really bring up my shoes again? “Well I am used to it. I actually love the feeling of wearing heels. I instantly feel 10 times sexier once they are on.” He smiled and said, “I can just imagine how that feels.” That was a weird answer. Maybe I am being too judgmental. I tried giving myself a pep talk in my head that I was being too hard on him. He is just different than what you are used to. Just have a good time and pray you don’t get another dick picture in the morning like you did with the last guy who took you to dinner.  “So, how long have you been at your company?” I tried to change the subject to get the topic away from my shoes. After we ate and had a few drinks he asked me “It’s still early. Would you like to go out to another bar for a few more drinks?” “I am really tired from the week. But I would like to see you again.” I was done with the date and was ready to go home. I did not feel a love connection but I was still curious. He was great on paper. Great looks, great age for me, great job, and family oriented. I would give him a second chance even though he had a weird obsession with my shoes. He started walking out to hail me a cab when he turned to me and wrapped his arms around my waist. “I have been thinking about kissing you since I watched you walk into that elevator 3 weeks ago.” He leaned in and kissed me. And it was really nice. He had really soft lips and a really gentle kiss. When he pulled away I almost leaned back in for another because it felt THAT GOOD but he brought his lips over to my ear instead and whispered, “I really like you. Jessika. And I love your shoes. I want to see how they look on me. I wish we were the same size so I could try them on.”  Completely unfazed by what he just said he turned to hail me that cab. I really tried my hardest to pick up my jaw from the ground and to wipe the confused and turned off look from my face. I just wanted to ignore what he just said. The cab pulled up and he looked at me for part 2 of the romantic kiss but that window had already closed with the shoe comment. I gave him my cheek and a smile and said “Thank you for dinner.” Then I got into the cab as quickly as I could without looking back up at him. I wonder how they would look on me???? Did he really say that? Did he want to wear my shoes? I did what any girl would do. I called my best friend and told her to meet me at our favorite bar, Matchless in Greenpoint, for emergency cocktails to discuss the freak show I just kissed on the street who wanted to wear my shoes. Dating can be a nightmare but they sure do make for good stories over cocktails with your girlfriends! I grabbed my phone and scrolled down to his name and selected BLOCK CONTACT.




  1. July 18, 2016 / 10:17 pm

    Hilarious! Great story lol. More! 😉

  2. Dino
    July 19, 2016 / 6:08 am

    Trinkets on the windowsill and shoe guy should meet each other so they can intertwine their souls or get some help together – I need ? After reading this. Looking forward to more. See you soon!!!

  3. Vilna
    July 25, 2016 / 1:15 pm

    I have no words…..O. M. G.

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