The Date (Girl Fail #10)

PoleStatistics show that the “…worst places to go on a first date include fast-food restaurants, your kids’ birthday party or school play, your parents’ house, strip clubs, X-rated films or swingers parties, a party where your ex will be, church activities, or window shopping.” How can strip clubs be on this list? It seems like every time I go there, women love me.  😉

After being dateless for over a year now, you can imagine how beguiled I was when someone accepted my invitation to dinner. By comparison, my date couldn’t have been more calm about it. Leah, an attractive marketing executive with curly brown hair, caught my eye at a bar a few weeks ago and our mutual sense of humor kept the conversation alive long enough for me to ask for her number. We texted pretty consistently throughout the following days and continued to hit it off. The great obstacle for me is deciding how to make the first date 1) memorable, 2) enjoyable, and 3) sexy/romantic.

My Plan:

An authentic Italian Italianrestaurant for dinner followed by a short stroll through the Village to a trendy jazz club

My Problems:

  • The menu’s all in Italian and, unlike her, I don’t speak the language
  • I’m allergic to 80% of all Italian food
  • I was excited and already over-thinking the date
  • Wearing nice shoes aren’t good for my bad knee
  • I cut my face shaving #RookieMistake


I suck at this part. Think about it. You try being an expert at a once-a-year activity. As far as I can tell, it comes down to two things; looking good and feeling good. Let’s start with looks.

Working out before a date is the pushup bra equivalent for men. After a long workout in the late morning, I knew that I’d look adequately fit for my date. Not to say that I’d be flexing at dinner but just as when someone shows their cleavage, I’d want to show a toned arm when I pour her a glass of wine. Next, I cleaned my apartment to the extent of my chances bringing her back there if the date went well. My chances this time were about a 5.5 out of 10, which meant I definitely had to clean my bathroom and bedroom. Also, I made my roommate aware of my chances and ordered him to keep his phone by his side in case a miracle occurs and she follows me home.

Then there’s feeling good. I showered as normal. I cut myself shaving but tried not to think about it. My thoughts raced in my head: Do I send her a text letting her know that I’m excited about tonight? Do I tell my parents what my plans are if they ask? No, I’m debonair and aloof – at least that’s what I’m trying to be. Should I bring a condom in case we end up at her place? No, that’s too bold of a move for a 5.5 out of 10 chance. Yikes, why am I asking myself this? Jesus, the date hasn’t even happened yet and I’m already thinking too much about sex. Why the hell did I pick an Italian restaurant anyway?

X rayNot only do I combat haphazard thoughts but my physical well-being was an issue as well. I suffered an injury a few years ago that left me with permanent knee damage. Meaning, if I wear anything but sneakers, it hurts to walk. But she was beautiful and I wanted to look nice for the date, so I threw on my black dress shoes, which tied my outfit together more than my Adidas’s.

The Date:

Feeling dignified and poised, I arrived 15 minutes early. I thought to grab a table but felt that it’d be best to greet her outside first. What will we talk about? I thought to myself. Eh, I suppose it doesn’t matter as long as the conversation doesn’t die out. Hell, it doesn’t even matter if I kiss her, I’m actually doing something tonight instead of jerking off. I have to at least congratulation myself for that! But she never showed. No message, no apology. Nothing.

The hostess asked me if I’d like a table. I shook my head and walked away. Stopping at a liquor store on the way home, I bought a bottle of Merlot. The rest of my night consisted of physical therapy exercises, since I could barely walk by the time I got to my apartment, and downing an entire bottle of wine. I was right about one thing though, I didn’t jerk off that evening.


And if you’re wondering why I titled this The Date when nothing actually happened, well, I suppose we’re in the same boat now, aren’t we?

-Single Guy in NYC


17 thoughts on “The Date (Girl Fail #10)

    • Granted, I’ll never know why but someone like her could get asked out every few weeks if she tried. Chances are I just grabbed a ticket and waited in line, hoping to be called.

      My next fail’s even worse.

  1. LOVE your blog! Very real, humorous, and well-written. It’s incredible how many blogs there are about being single in NYC; and such beautiful and thoughtful people! I hope you all find each other some day…

    I’m really sorry she treated you this way, but such a great post came out of the scenario. Do keep doing what you’re doing. I’m going to send some readers your way 🙂

    Captain Creme of the SS Relation(ship)

  2. WTF! Okay, I’m mad for you. I thought NYC men were bad, looks like NYC women are just as shitty! It blows my mind that people will stand someone up in this dat and age, when a MILLION ways to contact someone exist! She didn’t even send a text? Grrr- makes me mad for you! Ugh. Well, better luck next time. Hope your knee is feeling better.

    • Thanks, my knee did get better w/ some therapy. And you make an important point that there’s no excuse anymore not to inform someone in real time that they can’t make it. The way I see it, she probably had other dates already lined up and there was not much pressure to go to mine for whatever reason. Thanks for reading!

  3. Wow, I never considered what men do to prepare for a date, or the thought that goes into planning one! And I can’t believe she didn’t show up, that’s just plain rude. Don’t give up though, women aren’t all bad! 🙂

    • Glad to entertain.

      And agreed – women are lovely and amazing. Too bad people suck. My next Girl Fail will recount what happens when my date DOES show up. Improvement? It’s debatable.

  4. I agree with everyone else. Even having dates already lined up, there is no excuse to not simply send a text beforehand: “Sorry, can’t make it.” It is about having a little bit of consideration as well. Conclusion: Glad she didn’t show up, she is not the type of person that you need in your life.

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