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Dating in NYC: The Honest Sinner vs. The Phony Saint

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Disclaimer: To protect the identity of the men involved in this article – I am leaving out some specifics about them and these events. I will not disclose anything more about them publicly.  I don’t really want to get sued, or have anyone accuse me of slander…I didn’t write this to attack anyone – just as a cautionary tale.

Why do so many people deceive others when it comes to dating? I’ve heard countless stories about men and women who lie about their age, job, marital status, a previous divorce, a live-in partner, even children. People also hide their true intentions. They might act like they are looking for a serious relationship when they are really wanting no-strings attached sex. A man or woman might also pretend they want a casual relationship when he or she is secretly hoping for a committed one. I’m a huge advocate for truth. Honesty will get a person father than secrets and lies. I have two examples in my own personal life that illustrate this perfectly.

The Honest Sinner – An absolutely beautiful man who was over a decade younger than myself and someone I knew casually. When he approached me he was upfront.  He was looking for a casual sexual encounter, no strings, no expectations. Before our hook-up, he even sent me a text with the rules of engagement. It wasn’t exactly romantic, but I knew he wouldn’t try to coerce me into anything I didn’t want to do. I weighed my options, and considered I would take him up on his offer. It wasn’t just that I found him incredibly handsome, I also genuinely appreciated his candor. We ended up meeting, more than once, and the sex was great. I didn’t care if he was hooking up with anyone else, as I never really saw him as much of boyfriend material due to our age difference. I also knew he didn’t have a serious girlfriend so he wasn’t cheating on anyone. There was never any pretense. We didn’t go on dates, and neither one of us indicated that we wanted more out of the situation. I decided to cut it off when it wasn’t working for me anymore, but I actually grew to like him as a person. Sometimes these arrangements can lead to all sorts of misunderstandings and misery but in this example it worked out. His looks were definitely a factor of why I had a casual relationship with him, but his honesty is what sold it. Had he been sleazy or deceptive I wouldn’t have gone near him.

The Phony Saint – A moderately good-looking guy who I thought I might want to date seriously. He was closer to my age, had a good job and was extremely well-educated. He overall was a much better match for me on paper, and I was physically attracted to him. We seemed to get along well, but I barely knew him, so I honestly didn’t have strong feelings either way.

Things went South on our second date when I made the mistake of going back to his apartment. Within minutes he got extremely physical and I felt uncomfortable. His sexual energy made me feel like some sort of live action porn doll – and I just wanted it to stop. My instincts were correct when right before he actually tried to have sex with me, he called me Gillian instead of Juliet. As soon as I saw the condom, I shut everything down. Then I completely humiliated myself and burst into tears. It honestly was the first time I can remember, since maybe college, when I have had a total meltdown while on a date. I was mad at myself for letting things get this far, and I felt like a total idiot for crying. Deep down I knew something was incredibly inauthentic about him so I asked, “Do you do this all the time? Is this what you do with women?” He looked at me sheepishly and said, “Well yeah. I’m basically a child, I can’t have a serious relationship.”

This man had a professional job and was in his mid-thirties. He had also asked me out on a date, he wasn’t upfront about wanting just a hook-up. Unlike the Honest Sinner who kept all his correspondence sexual and to the point, The Phony Saint laid it on thick with multiple emails and texts as if he had some real interest in me. He even claimed to have looked me up online. When I point-blank asked him, “Which videos did you watch of me?” he responded, “Um, two. One of you getting interviewed on television and another one – I don’t remember.”  Now I don’t know how he couldn’t recall a short video he claimed to have watched just the day before, but I really didn’t care.  I knew he really didn’t really give a damn about me when he called me by the wrong name, and treated me like some sort of masturbation toy.

For the next extremely awkward hour, or so I apologized for crying while he begged me for various sex acts.  Even at the time I was unsure why I didn’t just walk out.  I got repeated inquiries from him to “jizz on my ass, stomach or tits”. He actually used the term “jizz” and seemed shocked that I had no interest. I might have honored his requests if I actually liked him, or if we had sex, but at that point it was just pathetic. I was just in shock that things had gone so badly so quickly and I wasn’t really sure what to do.  During all of this he danced around the room naked while speaking to me in a sing-song jokey way. I guess he was trying to cheer me up, but it just made him lose any remaining dignity. He then offered me leftover take out from his fridge.  When I say leftover takeout, I mean takeout that was at least a day old if not older.  I told him I didn’t want his “used food” and I refused to drink anything.   Any spark of sexual attraction I had towards him vanished, but I also calmed down and realized I was in no danger.  Things got even stranger when I realized he seemed to enjoy being chewed out by me. The Phony Saint just became a test subject to me of sorts. Thankfully I was completely sober, but my sobriety just meant I would remember every horrible detail of what was now, the worst date of my life.

So which man got what he wanted? The Honest Sinner got free sex from a consensual enthusiastic partner. The Phony Saint experienced an extremely embarrassing and sexually humiliating evening. If I could scrape that night from my brain I would, and yes it will make great material for my stand-up, but I have SO MUCH material already. HA!!!!!! I would have much rather had a lovely evening than another horror story to share onstage. Had he been honest from the beginning, I probably would have turned him down for sex as I get offers for that from total strangers all the time. The Honest Sinner was someone I knew already and that factored into my decision to hook-up with him. But even though I would have turned down the The Phony Saint, plenty of other women would have taken him up on the offer. He was good-looking, had a nice build, a great job and his own apartment – he had plenty of qualities that would get him laid in New York City.

The moral of this story: When in doubt, just tell the truth – everyone will be much happier for it, and no one will end up dancing around the room naked begging a women to let him – jizz on her butt.  Also, never call a woman by the wrong name when you’re trying to seduce her – it’s just bad form.
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Dating in NYC: How to self-sabotage a date

English: (ship) half-submerged and sinking.

English: (ship) half-submerged and sinking. (Photo credit: Wikipedia)

Anyway this is meant as self-deprecating humor.  I am after all a comedian.  I am a lousy dater because for my entire adult life I have been a serial monogamist so I really don’t know how to do the date thing.  I talk to much, I reveal too much, and I am too hyper…but I am hardly nasty and I have heard so many stories from both genders of people being extremely mean or shallow on these dates…so please anyone reading this…the piece was meant as satire, self-parody…don’t take it so seriously!  YIKES! 

Dating is not marriage, dating is one big job interview after another.  Marriage is trying to keep the job you have had for years already have interesting and exciting.  Going from a long-term marriage to the dating pool is rough, I have no idea what I am doing, but I do know when a date is clearly not going to work out.  And to avoid having “the talk” with some guy I barely know, I tend to instead self-sabotage the whole endeavor.   The “talk” is the short brief chat about why I don’t think we are compatible as a romantic couple.  I don’t like getting “the talk” from a man who isn’t interested in me, and I hate giving it.  Since I date mostly men I meet online, it is a total crap-shoot.  I can’t really tell much from a profile, and I have no idea if I will end up having any type of connection with the person.  Most of the time I don’t, and that is not their fault, but merely the nature of the beast.  I don’t get offended or upset when I can tell a man is not viewing me as a potential match.  It is the meeting of two total strangers, it is rare when sparks fly.

I don’t really understand what makes attraction work, but I do know that on a few dates I wanted to crawl over the table and start making out with a guy I had just met.  I didn’t publicly make-out with a total stranger, but in the two times that I have felt that right away, I ended up briefly dating those men.   The two suitors looked nothing alike and had totally different personalities, I can’t explain why both of them were appealing to me, but there it is.  When the initial attraction is not there and the conversation is forced or awkward, then it is time to have “the talk” or resort to self-sabotage.

There are generally two methods of self-sabotaging a date.  The first I call the super clingy needy crazy girl, sometimes the super clingy needy girl act can backfire, and it also makes you look crazier.

  • Talk about marriage immediately
  • Talk about babies immediately, wanting to have babies, your friends babies etc. anything about babies
  • Discuss with your date things that you will do in the far future, things like “I can’t wait to hang with you at Christmas!”
  • Ask way too many super personal questions right off the bat, such as “How many women have you slept with?”, or “How many girlfriends have you had?”
  • Talk about how much you love the man’s neighborhood and would love to live there

The dark torpedo – my preferred method and honestly I do this a bit subconsciously when I don’t even mean to go there.

  • Go on and on about my divorce
  • Talk about being on medication for my clinical depression due to my divorce
  • Ramble on about every ex-boyfriend I have had, or my ex-husband
  • Don’t ask the man any personal questions about himself
  • Discuss politics, history, world wars or something incredibly dark or horrible
  • Lament on all of my family drama and dysfunction
  • Say things like “I really shouldn’t be dating anyone right now”

The torpedo of darkness usually works, and the sad thing is that it sort of comes on me automatically.  It isn’t that I have a master plan and want to be mean, I just don’t watch my bad habits if I am not really into a guy.  And if he isn’t getting the hint I tend to lay it on even thicker.  I would rather have him think that I am broken and not available than to think it is something about him that I don’t like.  Because usually I don’t know why I am not attracted to the guy, I couldn’t tell you if you put a gun to my head.  It is just a quality that can’t be explained, but if it is not there, then it is not there.   I know I have gone through the opposite myself.

Some of my worst dating stories involve the following

  • A date who got noticeably offended and disgusted when I revealed I was from Missouri
  • Another man who bitched about an ex-girlfriend from….20 years ago.
  • A date who said his ex-wife was a bitch in the first five minutes
  • A date who proclaimed  “I don’t get emotionally attached” and then kept trying to steer the conversation to sex
  • A date who told me how much he missed his ex and hoped they would get back together
  • A man who openly told me he wanted to date a friend of mine – and yes this did happen.

If you are stuck in a situation where you think a guy is a decent fellow but you don’t really feel the urge to take the relationship further, use this as a simple guide to drive him away.  So far it has worked every time.  I accidentally learned these techniques from having one horrible date after another and trying to date too soon after I got divorced.   And if you meet a guy you actually want to see again, I strongly suggest you avoid doing any of the above, because you really want to look your best and not like a crazy clingy woman or a dark cloud of doom.