Let the Dating games begin…In the game, “Pin the tail on the Donkey.. Who is the Ass?”

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After a grueling few months of work, no dating, a 10 day holiday with my mother… I decided to put myself back out there on the market… not the job market, the dating market…

Do you remember playing, “Pin the tail on the Donkey” as a kid?  Online dating is kind of like that, but imagine a blend of Craigslist.com, Amazon.com & EBay.com without the review’s and it is a crapshoot on the photos.

My online dating rules  of mine have always been:

  1. They MUST have more than one photo. No excuses.
  2. Body shot photos are an automatic disqualification
  3. They must be local, must text, speak with and meet in a timely manner in a public place.
  4. People looking for pen pals or wanting to immediately send you dirty photos are automatically deleted/blocked.

So, I managed to post my profile, and the process begins… I get contacted by a guy who lives in NY, is within a few years of my age, yet younger, has 3 photos posted and seems cute. One of the photos is of his body clothed with a dog. We exchange emails, chat, text, and we even speak on the phone before he asked me out on a Friday night to meet. His name is Rob.

So, I end up meeting Rob at a local bar on my street, when I walk there.. I’m nervous because I hope that I will recognize him upon sight. Wishing for the best, I was walking up and I see a cute blonde guy smoking out front and he sees me, but doesn’t say anything…(damn). I keep walking into the long, dark bar and out of nowhere a guy that I never would’ve recognized as the guy in the photo. He greets me with a huge hug and “Hello Heather! ”Can I get you a drink?” Umm…WTF? Who is the guy in front of me?!

I’m still stifled and sitting there taking it all in, ask for a beer and staring at him trying to find a resemblance to the photo’s in the online dating ad. It’s not that he’s unattractive, but he’s not the same guy..Or the photos are old or something. He’s about 6ft tall, blonde hair, blue eyes, fit, and funny…he is telling me jokes and we start people watching because there is Karaoke at the bar where we meet and people are drunk, dancing everywhere, and it’s something of a show to watch. Hilarious…I finally let my guard down, but trying to figure out if I can leave.. There is no way out without getting by him. I cannot even go to the restroom and escape.. Ugh. I’m going with the attitude that, “I’m going to make the most of it!”….. “GO ALL IN or GO HOME!” and I couldn’t go home.. So, the adventure begins with Rob.

The evening ended up going really well, we actually ended up having a great time, he managed to talk his way back to my apartment and after much wine and conversation… slept over…ummm, yeah.. That too.

I woke up to having a man cuddling with me, kissing on me and asking me to lunch. I took his hand, kissed him back, and accepted his lunch invitation.

Let the games begin… In the game, “Pin the tail on the Donkey.. Who is the Ass?”

Winter brings…the Needy and the Angry

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So….I’m back to the beginning again… No longer a tourist, or a commuting traveler to the city weekly for business….as you guess, I am now living in New York City. My company managed to relocate me to New York City from St. Louis, Missouri in early 2011. Prior to this, I lived in my own home, then a great loft in Soulard (St. Louis), then half in a room with a Hoarder in New York City, then to a studio apartment on the Upper East Side that is no more than 400sq. feet, yet costs in rent way more than my mortgage and more than double the rent of the large loft in St. Louis.. Yeah, but I’m living in the Big Apple, this is the place where people tell you that your apartment size doesn’t matter because the point is never to stay home and to take advantage of what this incredible city has to offer and get out.. “Your apartment is only an extension of your closet!”… I always loved that explanation and, yes… I’ve used it myself…several times.

I’ve gone a few months since the Producer left the stage and decided that it was time to try to attempt dating again in New York City…

In comes the young, determined, bright Attorney on the rise… he was a nice kid, yeah… kid. We had almost 8 years between us and he was quite tall, handsome, nervous with me and out to impress. I’ll never forget when we met at an old Speakeasy in Soho that was serving specialty cocktails… we sat across one another talking… learning about one another…he was delighted when I walked in and commented that I appeared so much better in person.. He couldn’t get close, because he was seated across the table…so, as the night progressed, he managed to get me to try multiple special cocktails, and then talk me into going to grab dinner…where he couldn’t wait to kiss me. He was a nice guy, and we had a great night, but the fact that he lived in New Jersey, and was too young for me was a deal breaker. I never saw him again, but he called and etc. a few times… it just faded away…
I managed to keep up the dating circuit and managed to meet the “Angry” guy…This guy was a special case, we met in person, very curt, to the point after Thanksgiving… we talked like in an interview, he was attractive, we shared a pizza, ordered drinks… he wanted to “share” a drink. Now, one thing that you need to know about me is that, “I’m not one that like’s to share food, drinks or much of anything else”.

This was odd..”Let’s share a margarita?” After all, we were at an Italian restaurant in the Union Square area and I’d been drinking red wine? Who wouldn’t think a Margarita was a beverage of choice in an Italian establishment. In addition, Who shares a Margarita? We aren’t girlfriends..There were some red flags in the evening, like we had to pay with a cashier, I had my own check and well, he paid for a few items, the sharing of a drink, I understand sharing a pizza, but a drink? Then, he proceeded to ask me to come over Sunday to watch a football game at his place and he would cook us dinner and etc. somewhere in Hoboken, New Jersey. Hmm…. I’ve never been there… how bad can it be?!?

Sunday comes around and almost 2 hours later, I make it to the frosty pier of the Path train and am wondering the streets of Hoboken looking for this guy’s apartment… I hadn’t eaten because I was going to eat at his place… or so, I thought.

So, I get there… he doesn’t text me…or answer the phone, I’m lost. After waiting on a street corner in the cold December afternoon, he finally calls and directs me to where he lives… He lives in a small apartment, not much furniture… very guy like.

When I ask about food, he hands me a beer and told me that he has bought an “eggplant?” to cook for us. Then, I ask if he has a recipe. And it goes downhill from here… He managed to sift through dirty spices, an old pan and attempt to cut up and fry pieces of eggplant that were heavily seeded, sour and oil soaked in awful…. Meanwhile, I scream as I see 2 Mice walk across his apartment into his bedroom. At this time, he yelled at me like I was in the wrong for being alarmed with the rodents running across the room…as if this was normal. Hmm….

Considering that I had a 2 hour commute back home, the place was infested with rodents, I was starving and it was a school night, I managed to leave Hoboken unscathed, starving and got home… never to see either Hoboken or that guy ever again. He remained in touch, kept calling, emailing texting until I ultimately asked him to lose my number and never contact me again. As the temper got even worse and I unknowingly found out that no one in his family spoke with him, he lost his job and didn’t see why he was being shunned with his behavior….very bizarre. When I had tried to advise him of the situation in a different light, I was privy to see his other half… Mr. Hyde… The Angry fella that he erupted into quickly. He verbally assaulted me and that was it.

He managed to send me crazy texts 6-8 months later, even called me a year later and wanted to speak with me… needless to say, I replied nicely, but did not re-engage any conversations as he’d tried to attempt. He was nuts.

The Producer… aka Broadway…or Hollywood…

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So, my initiation to dating in New York City was not the typical transition, I aimed high in the Big city with Bright Lights… I landed a Broadway Producer to charm the pants off of me… literally.

As all good things must come to an end, we had our ups and downs… months of texts, stolen phone calls, and then he would just “appear” in NYCity and expect me to come running, drop everything.. see him between interviews with journalist’s, show’s and etc. You see, it was doomed from the beginning, as we lived in different dimensions.. I, the girl with the 9-5 job and he didn’t generally start his day until later, and then wouldn’t get out until after midnight. We met in dark corners of hotel bars, lounges, dinners in amazing places, I have seen the most amazing hotel’s in NYCity and most of his room’s had bigger bathroom’s than my entire apartment. Now, I know what it sounds like, but we also met for coffee and yes, he came to my tiny studio on Sunday morning one time pleading with me to stay in his life.

The last time that I saw him, he came to my place, we had an amazing talk, great evening together before he had to fly back to London… and I woke up to a note saying that he would be back in New York City in 3 weeks and would like to have dinner with me.. someplace “nice” xxx. Three weeks turned into months….

He managed to text me over the holidays simple smiley faces, or “xoxo, xxx” and etc.

I never saw him again, but I occasionally receive text messages. He’s now a very successful movie producer.

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