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Online Dating on Craigslist or How to Drive Yourself Insane!

Updated on November 10, 2016

Single in New York City

So here I am in New York City where a plethora of men await me. Dating has never been my forte but surely in this sea of men, provided by Craigslist, Match.com and Myspace I would find my one and only, my soul-mate, if the idea of a soul-mate really does exist. I put an ad on Craigslist, get 60 to 100 responses, initially feel good, then overwhelmed, like I have a never ending stack of paper on my desk that I have to sift through one by one. They all start sounding alike. I start to think we should have relationship resumes complete with references and current telephone numbers. It sure would cut through the crap. I had started to make a list of all the men I had gone out with and why they were incompatible. This list justified my lack of a relationship if not to my family and friends at least to myself. It made me think I wasn't crazy.

OK here it is:

  • He had cats and was allergic to dogs (I have a dog and am allergic to cats).
  • He loved the country and hated the city (do I really have to explain this one?).
  • He was an ex-Catholic priest who didn't like to argue (enough said).
  • He was a psycho vegetarian who had posters of old women and stuffed animals strewn throughout his apartment. I am not kidding nor am I exaggerating (more about him later).
  • He was obnoxious and could not quit talking about himself to save his life.
  • He didn't like it that I was a Christian, he was Jewish but didn't practice...go figure!
  • He was 100 pounds overweight and about 15 years older than his picture. I couldn't have picked him out of a line-up!
  • He was 6'5", I'm 4'10"
  • He was very small and tiny, unusually tiny, like freakishly tiny, (for some reason that bugged me).
  • He was poor and wanted to smuggle store bought beer into an already cheap bar.

Ok, so having gone over this list in my, beleaguered attempt at editing, it might sound as if I am a little picky, just a little mind you. But, in my defense I would counter that argument saying that this is New York City, there are more men here than say Boise, Idaho, there are more varieties of men and therefore more varieties of incompatible men. In Boise, Idaho (and I am not picking on Boise for all you Boisians out there, it could be anywhere outside of New York) you might have a choice between A. The poor guy who wanted to smuggle beer into a pub or B. the 6' 5" guy. But, here in New York City you have A through Z to choose from and they are all just a computer ad away. You can see my dilemma.

Talking to men online is like talking to the Velveteen Rabbit before he becomes real. They are all so anonymous, sometimes they are anonymous even after you meet them but it's really bad beforehand. I remedy this with note taking, it doesn't have the power of the Blue Fairy to make them real but it helps. The only thing that makes them real is "The Connection". Sometimes the connection can take one meeting or date, sometimes it takes several, but once the connection is made they become real. If you go out on a date and they don't become real, then that's it, no second date, no Blue Fairy magic, no nothing, just another Velveteen Rabbit. Oy, I could open up a toy store!

So what is a girl to do but close your eyes and pick one out of the hundreds of suitor/ads and go with it. Of course you will want to get a look at the all powerful and all encompassing PIC. So I pick one and go out. If I am lucky enough to meet someone who even remotely resembles his picture I am fortunate. Then comes the initial meeting. This is when you calculate in your mind with the wizardry of a top-notch computer whether this guy sitting across from you has any potential whatsoever in making your life better or whether you've just wasted another perfectly good evening, cynical I know but nevertheless. This is not to mention all the guys that you didn't pick that could have been the ONE. That concept alone drives me crazy. I mean for every guy you do go out with there are 100 that you don't go out with. So the odds are 100 to 1, they are not in your favor and it's maddening to think about.

Not that I think that I am Miss Wonderful. All the while my insecurities are whispering in my ear "you're too fat", "you are having a bad hair day", "you're too short", "you're talking too much, slow down", etc, etc. It's a wonder they don't have specialty nut houses for the terminally single!

So I agree to go out with this guy, yeah, yeah, yeah another Craigslist guy. We talk on the phone and he sounds a little nerdy but intelligent and I like guys who are a little nerdy but intelligent. So we talk on the phone a bit and yeah there isn't any chemistry but he lives close by and he's a writer and writer's are cool right :). So I agree to meet up with him. He is passing by my apartment and he wants to meet and I just happen to be making brownies and invite him in for some brownies. He stops by for a few minutes (enough for me to see if he is a horror or not) and he seems nice enough and looks good enough and I can hear all my friends and family in unison (can you hear them?) telling me how picky I am so I figure what the hell, I'll give him a shot. So, he asks me over to his place for dinner. I don't think too much of it because previously he said that he didn't like to go out to eat, so I said sure.


I arrive at his place. I knew that we were not a match when I spied out of the corner of my eye a furry gorilla, the size of a real gorilla sitting on a chair in his living room. I noticed another animal of the same stuffed species kind sitting on another chair, this one was a full-sized German Shepherd. The antenna is rising, the red flags are scrambling to reach the mast of the ship, full sail ahead! He then proceeds to show me the rest of his apartment, complete with more stuffed animals on his bed, in his bedroom, on his couch and in the closets. On the walls were life-sized cardboard cutouts of celebrities. The coup de grĂ¢ce was a bigger than life-sized cardboard cutout of an old woman in a wheelchair located in his bedroom where you could see her upon first waking up in the morning. Immediately, I regret not bringing a weapon and start talking to myself. You know the words: "just get through the night", "make a mental note of all exits", "make sure to mention you have a communicable disease of some sort in the dinner conversation", you know the usual fare.

He proceeds to make dinner as if he were a normal person. Dinner consists of steamed kale, millet and a veggie burger with onions, not your usual first date dinner, but why should anything be usual at this point? Two of the three items I had never consumed in my life. At this point I was trying to think of ways to become unbearably unattractive, if I could have manufactured a burp or two I would have gladly have done so, unfortunately I was not blessed with that talent. During dinner he is looking at me and telling me how beautiful I am. Under most any other circumstances I would have eaten that up, here and now I am considering telling him I have AIDS and only have 6 months to live. But, lady that I am I can't do it. So we finish eating and we go and sit on the couch with a nice liquor that didn't have nearly enough alcohol in it to make the night tolerable (do they make alcohol that is 200% proof ?). He then starts to tell me that he has a massage table in the back and how adept he is at massage. At this point I stand up and tell him I have an early morning appointment and quickly make my exit. Considering the way I left you would think that it was quite clear that I was not interested. But no, a couple of months later he called and asked me out saying that he thought that we had chemistry. I told him "no, no, there was definitely no chemistry, sorry", and that was it another Craigslist date in New York City.

It never ceases to amaze me how a potential partner can be so picture perfect on paper and yet so irreconcilably wrong in the real world. My qualifications or expertise in making this statement is my lifetime membership in every single matchmaking online singles dating site known to womankind. I should have an honorary degree in dating by now, instead I have another 6 months free membership to continue walking the purgatory known as singledom in your 40's. You know you are getting jaded when you look at your latest wink, nod or kiss with the focused objective of trying to figure out if the man who just winked at you might possibly have spent time in prison, is running a scam or has actually buried his last wife under the floorboards. It's difficult to remain open at this point. But, open-minded one must remain otherwise you might as well exchange your vacation spot in purgatory for a little convent in hell!


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