Creepy McDouchebag and His Dating Dont’s in NYC!


Sometimes people watching in NYC can be real fun. If you look around and just listen a bit there are some amazing things happening around us. I walked into my normal neighborhood coffee shop this morning to take my usual seat, connect to the free wifi, and settle in with a hot cup of joe. Being that it was a crappy weather night out I just went to the gym and then stayed in. I finally hit the hay a bit earlier to get a good night’s sleep. On a Friday nonetheless! Lawd have mercy! I feel good and actually got up early to get in here while it was still empty save for a few other early risers. As I sipped my coffee and perused my emails I also wondered what to write about today. Sometimes I have a few ideas swimming in my jumbled mind about a subject or two to ramble on about. I had nothing today other than cobwebs that the coffee was slowly beginning to erase from my brain. Then it came to me like a ray of sunlight breaking through the clouds. Enter Mr Alpha Male Creepy McCreeperstein! Sit back and enjoy the show as he totally destroys a date with what seemed like a nice girl. Grab your popcorn and take a seat on the couch. See the douchenozzle in his natural habitat!

first date one does not simply meme

Seriously, this was pure gold. It’s one of those moments in life when you leave in your earbuds but turn off the ipod to listen in and observe. It was that juicy. It’s like he ran the guy’s playbook on how to not get totally laid. All I was thinking through this whole thing as they were sitting right in front of me was to keep writing notes and not break out laughing at this douche. That, and I felt bad for this poor gal. You could tell the date was disintegrating and there was no way of stopping this train wreck.

She arrived first, grabbed a cup of coffee, and took a seat at a table in front of me. Well dressed in a flirty weekend way, but not overly done, attractive and had a smile on her face as she ordered. I detected a hint of a Russian or Polish accent. A few minutes later Dr Douchenstein walked in wearing a full power suit, leather man bag at his side, oozing of UES frat boy Wall Street smugness. You could tell he thought he was the shit just by listening to him for a few minutes. They probably met through an online dating site and thought this was a safe bet. He reminded me of Christian Bale’s charactor in American Psycho. Well coiffed but kinda swarmy. Inside I was screaming at her – “RUN! Get away while you still can! Saaaaaave yourselfffffff”!!!

american_psycho (1)

The conversation started out innocently enough. Two people getting to know one another. Where are you from? What do you do for a job? What college did you go to? What is your bra size? The normal stuff. Wait – what?!! Did he just ask her that? Yes he did! Commence turning off ipod! Sure, she was what you would consider nicely endowed in the chestal area, but dude really? You just met. Talk about an ice breaker as she nervously laughed off his question.

Now I see them order some food and he asked for seperate checks. Oh man, this is getting better. Mr Dickwad could not splurge for an egg sandwich and coffee for the lady? Yet, you are walking around with a $400 man bag/purse? I heard him comment something to the effect that she should watch her carbs or she will blow up. Yeah, nothing like insulting a lady to get her sexual arrousal juices flowing.


The next thing I notice is that he wants to show her something on his cell phone. He swears she will love it as it’s really funny. He keeps trying to put it in her face but she declines. He then drags his chair next to hers and creepily leers in at her bosom while almost sitting on her lap. Mind you this dude is around 6’2″ and she is maybe 5’4″ tops. He hits the play button and from my angle behind them I could see the phone. Sweet Lawd Jeebus he is showing her a PORN video! With full volume!


Are you fucking kidding me? In a public place? At this point you can tell she is mortified, and he quickly turns the volume down as he makes her watch it and does play by play. He keeps telling her how funny it is but she tells him she doesn’t find it humorous at all. He then says that “Anal is funny! Just look at her facial reactions”! I swear she was about to give this guy a facial across the nose. I shit you not – this is really happening right in front of me! I could not write this stuff down fast enough for this blog post!


Then, in his self righteous point of view he begins to throw attitude at her and starts pouting like she killed his puppy. He tells her she needs to loosen up and that she should be happy he met her this early in the morning. She explained that she needs to go to work later on and as a boss she was needed in today for a project deadline. He then tells her that women should not be in charge. She was too pretty to be a boss, and that pretty women make terrible leaders since all they care about are their looks. “Men like me are bred to be leaders, as that is the natural order” he proclaims. I started laughing so hard coffee shot out my nose and all over my keyboard at this point. I was sweating and hyperventilating desperately trying to not break down in hysterics. This guy was a total joke of a human being. I feel so sorry for the poor girl that gets into a relationship with this jackwipe. Can we say Stepford Wife here?

Ok, so now I can see this date has gone to Hell, and she is not happy at all. He is sitting across from her drinking his espresso and a death like silence has taken over the conversation. Staring at her. Out of the blue he asks her if she is attracted to him. He says that most women find him sexy and he gets a lot of girls. She is silent. He then gets up and tells her to not expect another date or text from him. As he walks out he tells her to have a nice life. Good riddance! She dodged a bullet on that one. As she finishes off her coffee alone I feel so bad for her, but relieved in the fact that this shit stain will not ever procreate with her. Unless she actually is dumb enough to contact him again. Lose his number please.


As I get older and observe the world around me it has really come to mind that this generation of younger men are really clueless about how to date and treat a woman. I can also imagine if this is how they act when on a date how that must reflect on their abilities in the bedroom. Lame-O! Now, I know this is not all men but I do see it all too often here in NYC, especially with guys under 30 it seems. I’ll admit I was a bit of a douche too when it came to dating in my skirt chasing dog days. I was no angel, but after a while I learned, and realized these tactics are not the way to get more play. It’s all about the skills my brethren.

Not all women adhere to the “treat me like a bro, put me down, and make me eat shit” way of flirting. What happened to being a gentleman, treating a woman right, and flirting in a playful sexy way? Too many men nowadays are social misfits and the basis of their communication is through the web and internet porn. I think it’s how they learn this crap. Sure, dating in NYC nowadays is like a sport along with certain game rules to adhere to. So glad I don’t have to deal with it. Dating today is like competing in a demolition derby!



Get a clue guys. Really.

76 thoughts on “Creepy McDouchebag and His Dating Dont’s in NYC!”

  1. Omg, That is too funny. I think I would have said something. I can’t contain myself sometimes lol then coffee on the computer was awesome. Bra size wow. It’s so sad it’s just not men it’s everyone.

    1. Hey Patricia!

      Can you imagine if women asked a guy what his penis size was on a first date?

      Then again, some might whip it out to show her!

      1. HI PHIL…






  2. Wow, so THAT was what you were talking about while we were emailing back and forth that morning. Sadly, going dutch was the smallest of this guy’s crimes. He didn’t even treat her like a bro. You wouldn’t even talk to a potential male buddy that you were meeting for the first time that poorly.

    It sounds to me like the guy has no clue what respect, personal space or sexual harassment mean. I’m sure he’ll go far in life. Well, maybe professionally. I’m also sure some Madam somewhere will make a ton of money off his inability to get a “date” of his own.

  3. Ugh. Ok, that bag of crabs beats my bad dates. On a first date once the guy told me he was separated from his wife (I had no clue he was married) because he is in love with a married woman from his running group. Not was, IS madly in love with her but she won’t leave her husband. After the shock wore off and I didn’t give a crap, I just started laughing and asking him tons of questions. He was a clueless douche tunnel but he was so bad he was funny. Yeah, no second date.

  4. I basically laughed reading this but, Omg what a shame for the girl! She definitely got a lucky escape! What a total idiot of a guy and no wonder he is single!

  5. That was hilarious. That bloke must have thought he was god on earth to behave like that. And to think that there are some women who would fall for it because they saw a well dressed guy with a man-bag and money.
    She should have grabbed him under the table by the lower regions and twisted hard until he sang like a bird with an apology. This would have brought him back to his senses.

  6. My heart goes out to this girl. While that is an incredibly entertaining story it can really mess with your head when you’re the girl. You know he sucks, but this might be the 5th sucky guy she’s encountered and that can make even the strongest, most confident woman feel jaded and sad. I hope the next guy (or girl) is amazing for her.

    Ok, I meant all that nice stuff… but REALLY?! Who the hell does that guy think he is. Like a cartoon model of bad male etiquette. I’m older now, and once realizing how bad he was I would have gone into full insult-sarcastic mode. The audacity… Damn.

  7. Phil, you should work for the NSA. : ) Seriously, I can’t believe what a waste of human DNA that guy was. What an arrogant asshole. I’m glad you were there to capture it in real time. I can’t believe he asked her about her bra size unless he was a bra salesman.

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  9. Wow! It never ceases to amaze me that guys like this crawl the face of the earth (like insects). If it wasn’t for the fact that this poor young woman had to suffer, I would say bring on the crazies, because blog material-wise, it doesn’t get much better than this! Of course, not sure I would have been able to keep my big mouth shut, especially with the bra size question. I think she should have immediately speculated as to the size of his, well, you know…although that might have turned the douchebag on. Yuck, yuck, yuck.

  10. A tragic date, only made right by the fact that you were there to witness it and regurgitate it for our amusement! Wow. Just wow. Really? These type of idiots still exist? Actually why should I be surprised.

  11. Holy cow that is infuriating! I was getting so mad reading this because i just feel so bad for the poor girl. Men like that suck so bad . Ugh, i had flashbacks on some of my whopper bad dates!

  12. Oh man, that was gold. If I had been on that date I am not sure if I would have stormed out or just let it play out for the sake of blogging about it later. It is hard to believe that anyone could be so clueless as to think that those were okay things to do on a first date. It’s almost like he had been dared to make the date go as horribly as possible. Who are the women out there responding positively to that kind of crap? I love the headphones in, ipod off move. I do that too, but only when things get juicy like you said. I’m like stop everything, this conversation needs my full attention. Shit just got real.

    1. Hey Everyone!

      It was pure juicy Jerry Springer stuff!

      I don’t think he was dared. I just think that is how this douchenozzle is. Yes, the ipod and earbuds are a wonderful eavesdropping device!

  13. I . . . oh, sorry about that, I’m back now. Read this and had to run off and call my husband and say “thank you”. I would NOT want to be out in the dating world right now {{shudder}}.

    Although I have to admit I’m infinitely amused by your telling of this story.

    1. Hey Karen!

      Ha! Go give your guy a big hug and bake an extra tray of cookies!

      Glad you got a smile out of this. That girl wasn’t too happy though. This guy was a cartoon charactor!

  14. Oh my God Phil! WTF?! I have to share this on my Facebook page because this is beyond comprehension and I laughed my ass off reading your recap of what you just witnessed. WOW. What a fucking douchebag! I agree with you that this generation is incapable of knowing how to communicate, let alone follow the rules of flirting all because of our social media and porn.

    This guy CLEARLY is clueless and doesn’t understand that something he may think of as funny doesn’t mean the next person will also think of it is funny too, especially when it comes to showing not just a porn video, but anal?! on a first date?!!! Good lawd, face palm is all I could do when I read that. My mouth was just dropped as I kept reading and I feel so bad for that girl. Good for her for not saying anything more, she was probably speechless as we all are. To also offend her and say that she should not be a leader and to make a generalization that pretty women just need to be pretty is just INSULTING!

    When you started laughing at him and spilled your coffee, I was dying laughing with you. I could just picture you trying not to be obvious that you were listening in on their conversation. Glad you did though because it shows us that some men are THAT stupid. It’s apparent that she went on the date with him because he looked GOOD on the outside, but man was she in for a surprise because he is not matching the outside with the inside.

    Great post! Glad to see that you are one of the good guys who knows how to treat a woman. This douchebag has a long way to go before he hopefully learns his lesson.

    1. Hey Bella!

      Knowing your dating exploits I was sure you would get a kick out of this one!

      Face palm for sure! I was hiding behind my computer listening in the whole time. Hopefully that gal’s next date will go much smoother!

  15. Hi Guy, what-a-creep! Poor girl for even staying that long. She should have walked out a long time ago, but what a great day for you. As far as the day-to-day goes, you couldn’t make it up.

    I live in Berlin and I once saw this American guy chatting to a German woman on the Tube. She didn’t respond and he got more and more heated. In fact, he started swearing and using pretty strong language. No response. He was beginning to get pretty upset. Because I’m British, I understood everything he said and the German people around didn’t understand why he was getting heated. I was also sitting opposite him and noticed that underneath the lady’s long hair were ipod earphones. She hadn’t heard him!
    I could have told her I suppose, but he was enormously rude, so I didn’t!

  16. I think I dated that guy! Came from Susie Landau’s Wild Ride & glad I joined in today! I don’t know how you sat there without bursting into wild laughter! Thanks for a great laugh.

    1. Hello Benzeknees!

      Thanks so much for dropping by and commenting! Sorry for the delayed reply. Just playing catchup now.

      I was snickering the whole time! At one point I had to look away and surf the net or I would have broke out in a laughing fit!

      Hope you can follow my blog!

  17. Thanks so much to Susie Lindau for sending me over to say hello.

    People say New York is expensive, but with all the free entertainment, I can’t agree. I try to get back a few times a year and last time I was in Veselka’s in the middle of the night watching the couple in the next booth. The poor woman stared at him like she was witnessing a train wreck. She couldn’t look away and either could we. Before their food even arrived, the guy confessed that he might have left out a few things on the online dating profile, including being married (but that was his old bitch’s fault because after that last time she called the cops and lied about him hitting her, she disappeared) and fessed up to actually being unemployed (he said he was a writer because, you know, they make a lot of money and he’s got some great stories, and he was really thinking about writing them down), on parole (totally not his fault but you know how the cops lie — just like his old bitch), to wondering if she lived alone and might be in the market for a roommate. As we were getting in a taxi, she came running out of the restaurant so we asked her to get in with us. Sadly, she didn’t have far to go so we never got the whole story, but she did say she would be cancelling her membership on that dating site. She thanked us for the ride, and we thanked her for the entertainment. Pierogi and a floor show for $10. Win, win.

    1. Hey Barb!

      Thanks so much for dropping by and commenting! Sorry for the delayed reply. Just playing catchup now.

      I have been to Veselka’s many times! Pierogi and a disaster date for the win! Your story had me laughing out loud here at my office. I bet he goes on many of those dates. Poor gals.

      Hope you will follow my blog!

  18. I laughed as I remember traveling from the Queens Main Library branch on the Q83 bus. I’m in my 50’s still a little attractive but very over weight due to being on steroids a long time. This man gets on the bus with a cane and several grocery bags. He puts the bags in the area by the door than sits next to me. He tells me he has pins in both shoulders, two knee replacements, pins in his hips and a rod in his back. I nod my head and say I know we are falling apart as we age. He the tells me he has a pension from the military, a pension from a city job, another pension from a federal job and his SS. Then he leans in and says I live alone if you want to work off some of that weight he will be glad to help him. Only in NY. This was an older man. Anyway Susie sent me. Nice to meet you and happy New Year.

    1. Hey Kim!

      Thanks so much for dropping by and commenting! Sorry for the delayed reply. Just playing catchup now.

      Hahaha! Love that Story. Give him props for trying even though it sounds like he would fall apart in bed!

      My gal had major neck surgery and is also on steriods and drugs so I know what you mean.

      Hope you will follow my blog!

  19. Reading your post, I couldn’t help but wish I had been there eavesdropping. I would have totally pretended to be some old friend of that girl and attempted to throw her a lifeline. Sadly, guys like this aren’t as rare as we’d like to think. I’ve encountered more than a few.

    (Susie sent me 🙂 )

    1. Hey Amber!

      Thanks so much for dropping by and commenting! Sorry for the delayed reply. Just playing catchup now.

      I would have thought she had an escape plan set up for bad dates but alas she was trapped there. So glad this dunce walked out.

      Hope you will follow my blog!

  20. That was AWESOME. Found you through Susie Lindau’s blog.

    Reminds me of this couple my wife and I saw at a restaurant on a date. They were later middle age, and he was nowhere near as bad as Douchenstein’s Monster was, but she had a deer in the headlights look the whole time as he dominated the conversation and weird phrases kept drifting to my ears.

    The only one I really remember was this, as he spoek with eyes wide and emphatic gestures: “I mean… if I were a Jewish Rabbi… you wouldn’t offer me a DAMNED THING.”

    That girl really needed an escape phone call.

    1. Hey J Ensis!

      Thanks so much for dropping by and commenting! Sorry for the delayed reply. Just playing catchup now.

      So glad you liked my post. So, that sounds like it was a strange date. What is wrong with guys nowadays? Hope she escaped later on!

      Hope you will follow my blog!

  21. Hey there Regular Guy – Susie sent me and I’m glad she did.

    What an awesome post. I left a more detailed comment on Susie’s post as a reply to yours.

    Too, funny.

    Patricia Rickrode
    w/a Jansen Schmidt

    1. Hello Patricia!

      Thanks so much for dropping by and commenting! Sorry for the delayed reply. Just playing catchup now.

      Glad you got a laugh and liked this. I’m sure the gal on the date wasn’t too thrilled. Yeah, Susie throws a good party!

      Hope you will follow my blog!

  22. I just read this to my daughter Courtney and she says she has witnessed similar, but much milder situations. I can’t believe she didn’t dump her coffee in his lap!
    I would have!
    Thanks for bringing this to the party!

    1. Hey Susie!

      Thanks so much for throwing a great blog party and letting me be a part of it!

      It seems many women have experienced this kind of douchenozzle at one time.

  23. You have the best stories, Phil! This makes the date I went on look like a gem and he called an ex a C-U-Next-Tuesday, made racist remarks, and degraded the underwear choices of the women he dated. Oddly enough, he did ask me if I was attracted to him (no!) which just might make these guys brothers. Great submission for Susie’s party!

  24. Wow. Yep, these guys are 100% real. This is hilarious and tragic. Wish she’s slapped him. Illustrates reason #2388 I’m not looking forward to getting back in the NYC game…

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