Is It Okay To Act Desperate?

Depending on sample size, location, and attractiveness, the average match ratio for men on Tinder is typically under 10%. In densely populated areas, it generally drops to less than half of that. With all things considered, it’s easy to get desperate like Pepé Le Pew if these are your odds at just landing a match; let alone a reply; let alone a conversation; let alone a date; let alone a relationship. It’s helpful to set your expectations way down low and not respond like this dude:


However, knowing what it’s like, I don’t blame this guy one bit – maybe go easy on the CAPS lock next time though. Just a thought.

Here’s to all the Pepé Le Pew’s out there. I feel for ya!

I’m right there with you – sort of. Dammit, you know what I bloody well mean.

-Single Guy in NYC


Girl Fail #22 (Ladybug)

A wise poet once defined love as two solitudes that meet, protect and greet each other. Although I don’t expect this to be a revealing statement, notice how “solitude” is the subject – the polar opposite of partnership.

This is my story of such a love.

Our first date was simple; Sunday lunch and a walk on the High Line (a public park built on an elevated freight rail line). There wasn’t a stream of silence lasting more than 30 seconds the entire time we were together. Her voice was gentle and silvery but words will always – as expected – fall short of the ineffable. Something about her timbre was soothing. Her face was also gentle, a little glossy and perfectly aged to 29. No makeup. A little fat to her cheeks with a light skinned mole on her right side. Her smokey brown eyes were comforting. Her wavy hair, stretching down a few inches past her bony shoulders, reflected a similar shade of brown. It was slightly frizzy but compellingly natural. No bangs. She made few attempts to conceal her age. Her hands were perfection; nails weren’t chewed but grown out a few millimeters past her digits, the sort of hands that give the impression of prescient dexterity despite knowing nothing of their history.

She was older, which probably meant she was taking a chance on me, a writer and a Yale graduate. I anticipated her intelligence but her wittiness and sense of humor was bewitching. (Not to sound sexist but from my experience, most women excel in replenishing flirtatious banter but not in the instigation. She was assertive and could craft a great joke.)  Her analytical mind and serene temperament matched my own but luckily we were able to break that wall from time to time with an invigorating story, like the one about the Muffin Man.

No, not the one who lives on Mulberry Lane but of Samuel Bath Thomas; creator of Thomas English Muffins.

“He actually moved to the city, right around here, about a century ago,” I explained.

“There was a serial killer in Alaska named the Muffin Man. Is it bad that I thought you were talking about that?”

“Are you serious? Now I’m imagining him outlining bodies with blueberry muffins – you know, instead of a chalk outline.”

“Think of all the wasted muffins. And who wanders around with a box of muffin mix and a cleaver?” she added with a smirk. “What if Thomas English Muffins is just a cover up?!? You better call Alaskan police.”

“Holy shit, we just cracked this case wide open!”

This repartee actually continued for several minutes and became hysterically detailed but you get the drift. The first date was a success, so we made plans for a second.

Plan:    An evening of bowling

Problem:    She was busy every evening

Solution:     Bowl at 10am on a weekday after a couple of waffles from a local diner

Unable to tell her I, too, was busy, and afraid of losing a second date, I called my boss and took off work in order to bowl on a brisk November Monday morning. Despite not having many vacation days, this made me look adventurous and a tad bit silly (hopefully).

“When one is in love, one always begins by deceiving one’s self, and one always ends by deceiving others. That is what the world calls a romance.”  – Oscar Wilde

Breakfast was first. Conversation came easy and topics ranged from Lethal Weapon to Lady Gaga to Zen Buddhism to friendships to philosophy to roommates to writing to meditation to cooking and on and on. One topic would branch into a dozen separate tangents that we both had countless thoughts on. Never in my life have I been able to engage with someone on some many levels. She wasn’t an acquaintance I’m seeing for the second time, she was an old companion. Least, that’s what it felt like.

Do you know those self-adhering paper napkin bands that are wrapped around silverware?


Well, a playful thing I like to do is to make paper airplanes out of them to throw at my frog.jpgdates. What I didn’t expect was that she retaliated with a paper stealth bomber. In actuality, she made a paper frog that you could bounce but it looked more like a aircraft to me. She had an equal or greater response to everything, as if she was returning the favor in an attempt to woo me as well. Boredom was not in the cards that morning, or any morning as long as it was with her.

Bowling was second and we had the entire alley to ourselves for our first game.

Where have the women like this been all my life? You see, I’m analytical and skeptical. Which means I inexorably scrutinize the world around me. On top of this, I obsess over philosophy and the nature of the mind, which none of my friends do, or if they do, I lead the conversation. This was the first time where I was well matched, so to speak, and could freely express my ideas without being misunderstood. I was a prisoner of solitude finally being let out. It tickled my brain and electrified my body to connect in this way, if only I could contain that ecstasy in a jar for future use.

After my fifth gutter, it became clear how many ersatz relationships I’ve had; that is, cheap imitations of this. Humility in intelligence is sexy. So, if she had something to say, I wanted to listen. My tenpins game is amateurish at best but it grew worse because I kept my attention on what my next joke or thought would be. Pulling it together, I managed a spare.

“Woah!” she cheered. “These graphics are ridiculous.”

She was referring to the cheap animation on the TVs overhead. One such graphic was a silhouette of a woman (like in the opening credits of James Bond).

“Some Asian lady wearing jeans comes up when you bowl a spare!” she observed.

“It’s a silhouette. How can you TELL she’s Asian? Let along an Asian wearing jeans?”

“She’s got chopsticks in her hair!”

“Oh yeah? And what brand jeans? Levi’s?”

“Sounds about right.”

This went on for a while until we were both laughing with exhaustion. There may have been tears.

After dominating the first game, she suggested that for the next round, whoever wins the frame gets to ask the other person a question. Challenge accepted! And challenge lost.

She won all but a couple of frames and consequently, asked me quite a lot of questions. What were you like with girls in High School? What do you do for Thanksgiving? How does your brain work? How do you form thoughts? What are your guilty pleasures? How private of a person are you?

Be honest, dear reader, how many dates have you been on where someone asks how your brain works? This was by far my favorite query and I knew exactly how to answer. I connected my response to a few heroes of mine, one of them being Bertrand Russell.

“I wish I could write about philosophy the way Russell did,” she commented.

At that moment, I wanted to throw my arms around her and kiss her. Not because good ol’ Russell turns me on but because I finally met someone who feels the same way about his writing and how pragmatically beautiful it is. But alas, I had to keep my composure and not melt at her feet.

“Make your ego porous. Will is of little importance, complaining is nothing, fame is nothing. Openness, patience, receptivity, solitude is everything.”  – Rainer Maria Rilke

Prior to leaving the alley, we discussed what to do for our third date. Needless to say, we felt satisfied while making our way to an uptown R train.

After feeling the jolt of the train car at her stop, we kissed and she got off. Staying put, I watched her take a right out the doors and begin walking away. Just before escaping my line of vision, she turned around smiling, and waved to me. In that moment, I was the king of the world. I was so content that afternoon that I missed my stop.

That was the last time I saw her. A few hours later, we had the following conversation:


Scanning that first text, I was crassly catapulted from my “date high” and slammed into my seat. Without any gain, I felt 100 pounds heavier. Good grief. And while I will never know if she was telling her entire side of the story, I was slighted by her insinuation that I don’t fall into the “touchy-feely/artsy-fartsy” category. The irony in that sentence may very well spark an identity crisis within me.

And yet, I’m not here to object her underpinnings. All pithy rhetoric aside, everyone uses the first couple dates to suss out how romantic they are willing to get with someone. You’re unknowingly asking yourself: Is this the guy I want to give birthday blowjobs to? Is this the woman I want to thrust into on the kitchen floor or in the shower, when the roommies are gone? 

“Among men, sex sometimes results in intimacy; among women, intimacy sometimes results in sex.”    – Barbara Cartland

To me, she was providential. To her, I was a decent guy to play tenpins with.

Here’s the best part, even her rejection text is FAR superior compared to the countless I’ve received. Most people would have remorselessly ignored my follow ups.

Any silver lining? Sure. A few months ago, I wrote a post entitled She Makes Me Wanna Die (Girl Fail #21) about an ex that – up until now – I considered to be the love of my life. For years, I wasn’t sure if I’d ever find a connection truly worth keeping until now. Just knowing that I can feel this way again is a victory.

But the truth is unsettling all the while. I keep telling myself you will forget her silvery voice; her gentle face; her smokey brown eyes; her wavy hair; her perfect hands. After all, much of her body will remain undisclosed and a complete mystery to me.

If I bumped into her on the street, I’d want to tell her that she’d been on my mind every single day since we met. How every idle moment seems to effortlessly, albeit not painlessly, default to an affectionate thought of her. Of course, I could never confess this. Ironically, that’s no way to treat a lady.

{If by some astronomical chance YOU (the subject of my post; you who dreams of being James Bond) ever read this, I hope it finds you in good spirits. You never need doubt your ability to create a spark in someone else. P.S. I hope I made you smile at least once here.}

-Single Guy in NYC

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

Mind if I just murder this conversation? (Girl Fail #5)

There’s nothing like going to your favorite bar with your pals. As a single guy, I now look at these moments as canny opportunities to assist my friends in refining their wing-man skills. While grabbing a drink at the bar, I hear “Did all three of you just come from work?” Two girls sitting at the bar were turned towards us and after being asked just one simple question, it was quite easy to start a conversation. Following the standard name introductions, topics ranged from movies, music, religion, college, and travel. Needless to say that within the span of an hour, we knew a good amount about one another.

Rachel had my interest. She was laid back, confident, Jewish, and a straight shooter. The problem was that she didn’t do much to add to the conversation. It seemed like she expected the men to play 20 questions and try not to have it appear like a job interview. This is not only a challenge but agonizingly annoying. Yet, why not give it a shot? Nothing better to do.

“What do you do?” I asked.


“Ah, how did enlightening the city’s youth go this week?”


This isn’t to say that she didn’t have a personality – she did. But having a conversation with her outside of the group conversation that my buddies were having with her friend was unnecessarily difficult. Granted, she didn’t always provide a one word response but she didn’t show much interest either. After an hour, Rachel’s friend left but Rachel stayed to have another drink with us. At the end of the night, while Rachel was in the bathroom, my friend Mick told me that he overheard her complaining about her love life to her friend – saying that she doesn’t have anyone and it’s been a long time, blah blah blah. “We’re not exactly hitting it off though. You think I should ask for her number anyway?” “Of course! She didn’t leave when her friend left, so she’s expecting something tonight.”

To my surprise, her face lit up with charismatic delight when I asked her for her number. Maybe I was wrong. Was there a connection? Due to scheduling conflicts, we couldn’t get together right away. For a couple weeks, we texted a bunch and I came to realize that we had more in common than I thought. Finally, after 3 weeks, we were able to plan on getting together at a hip bar in Manhattan.

I HAVE A DATE. How do people prepare for this stuff again? Shower? Find clothing? Trim your pubes? All of the aforementioned? Ah,but as always, your luck catches up with you.

After planning out the evening, she texted me the day before our night out. She wanted to tell me that because I wasn’t Jewish, we couldn’t have a relationship. If we went out, it’d be strictly platonic. “I’ll convert!” I texted back, followed by cancelling the date. It’s interesting because I swear to you that I actually felt the joy escape from my body like it was a restless captive.  Till next time.

– Single Guy in NYC


Zach Galifianakis (Girl Fail #4)

If you think about it, being a single guy on Valentine’s Day has its advantages because all the single ladies (#Beyonce) go out to the bars with their other single friends. Thus, I decided to go out this past Valentine’s Day and test my luck. Getting off the train, I ventured to find the perfect bar to test my theory. After walking past a few bars, I noticed a five dollar bill on the pavement. As I reached down to pick it up, something caught my eye. There was a wad of cash a foot away from the $5 bill. There’s no doubt that this was drug money and it was my humbled responsibility to spend it wisely. So, I put a skip to my step as I surreptitiously scooped up the cash and headed for cover inside the closest bar.

I felt like a million bucks – well, $287 to be exact. Hell, I tend to spend close to $100 on my date this time of year and now I’m making money (it made me wonder if Cupid shot an actual arrow at a handler, who then dropped their cash onto the ground for me to find). Fully loaded and a grin on my face, I requested the best draft in the house and walked up to two pretty brunettes outside the bar’s backroom (which contained live music).

“Hi. I was wondering, do you know who’s playing tonight?” I asked. One of the girls, wearing a black and white striped shirt, smiled at me and said they didn’t know but their friend was playing after this band was done.We spoke for another minute before I departed saying, “I’m going to catch the rest of their set, maybe I’ll see you both in there.” A couple songs later, they showed up. It’s a small backroom and everyone stands within visible distance from everyone else. The entertainment was a hipster folk trio fronted by Zach Galifianakis’s part time impersonator and full time doppelgänger. I stayed in the backroom through their set as well as the subsequent band’s set. Afterwards, I decided to get myself one last drink at the bar, where I ran into the two girls again.

Seeing that one of the girls was with the drummer from the last band, I addressed the girl wearing the striped shirt again. “Hello again.” “Hi!” “So, what did you think of the Zach Galifianakis impersonator hipster group?” It was at this point that I realized 3 and 1/2 beers does, in fact, impair one’s speech. What actually came out of my mouth was “Zoe, hat did yoo tink of the Zach Gal-ee-poe-fank-us em-bur-sonator hipster croop?” She shook her head saying, “What was that?” Luckily I was able to bounce back, enunciate, and render laughter. Mind you, she was inebriated as well. We flirted for another 30 minutes until I told her that I was heading out and if I could have her number. She smiled as I took out my phone and entered her in. Then, I realized that I never got her name and never introduced myself. “I’m Single Guy in NYC by the way,” I said as I extended my hand. “Jo,” she replied. The second mistake I made was not texting her right with my name after leaving the bar. THIS IS A MUST to all you single folks.

I texted her two days later: “Hi, how’s it going? This is Single Guy in NYC – we met Friday night at____ after watching the   Galifianakis folk group”.

She never responded. So, instead of using drug money on a profligate first date, I bought myself something nice. Her loss; my gain? Perhaps.

– Single Guy in NYC