NYC Dating Disaster

Dating is hard enough, but dating in NYC is harder

On Friends and Lovers

After a long day in the private equity industry, Sarah and I decided to do a bit of shopping.  No, this is not the time to be spending frivolously, though I was in desperate need of retail therapy as I was also on the verge of alcoholism; which may actually be the better option considering the latest rays of economic optimism; cheap bottle of Yellow Tail vs. $200 Gilt Group tab.  Oh the decisions.

Because the future of our employment is so uncertain we decided that buying yet another suit may be necessary.  In addition to the gray, navy, and black pinstripe…everyone could use a crisp, linen…charcoal shift dress and matching jacket…right???

While advising each other on our picks in the Banana Republic fitting room, Sarah and I began discussing our love interests…

“So any promising suitors?”, I asked.

“Eh, only eye candy.  What about you?”

“Oh, well…I have the most painful crush right now.  You know, love hurts.”, I laughed.

“Rrreally??”, asked Sarah, “who is the crush??”

Before today, I had hinted to Sarah on a few occasions that my crush was Cole, though never admitted it.

“Well”, I began, “He is not the typical type of guy who I like…which means he seems to have his shit together.”, I chuckled.

Rolling my eyes and exhaling the deep breath that I just took in, “It’s Cole,”  I breathed.

Sarah looked at me and her smile turned further upward and she began to laugh, “That’s my crush!!!!”

We were jumping around in the dressing room like schoolgirls while wearing our cute little dresses complete with price tags.

I began laughing and grabbed her hands in mine while asking, “Doesn’t his ass look like it was sewn into his trousers?!?!?!  And I bet those trousers would look great on the floor!”

“Yes!!”, she agreed, “each time he bends over, I could swear that I am going to faint and need medical attention.”

“You know Sarah, if we were any other two girls, this could turn ugly, though strangely I  see this crush as bringing us closer”, I said.

Sarah agreed saying, “It’s like our little secret…”

“Our little secret about Cutie Bend Over…or C.B.O. for short,” I winked.

“OOOOH you’re bad!  I love it!”, Sarah exclaimed.

Taking this last comment as a compliment, I said, “Eh I try…we’ll be completely fair when it comes to love…and a great, tight ass.”  –Frankie

September 11, 2009 Posted by datedemall | Friendship, Interoffice Dating, New York, Sex, Work, dating, economy, relationships | , , , , , , , , , , , , , , , , , , , , | 1 Comment

Hittin’ the Kiddie Pool

Yes, I was M.I.A. for a few weeks; my apologies. When RD Capital Partners instituted a week long furlough for its employees what could I do but book a flight outta here?   Kim just graduated from Arizona State University; you know it I am sure–A.S.U.–the largest party school in this fine country. So what?  I am a twenty…ummm…well young professional in her late twenties.  A little dip in the kiddie pool never hurt anyone.  Time for some action.

From the airport, we stopped at our hotel to unpack before heading out to begin the festivities.  Kim said to me, “Just so you know, the condoms are here,” as she held up a long strip of  rubbers and then stashed them in a toiletries bag.  “Thanks baby,” I replied, “though I am not hooking up on this trip.  Your friends are waaaaaay too young.”  Kim gave a dubious stare and repeated, “As I said, the protection is right here.”  To which I had no response, except a smirk and chuckle.  The second stop on the welcome train was Loco Patron which had drink specials for the those who are still blessed with the financial backing of their parents, a.k.a. the under 25 set.  Oh yes, $3 bomber Thursdays; I can not tell a lie, getting bombed was a  theme of this trip.  Kim and I met up with her friends Mike, Cory, and Charlie; all of whom were almost old enough to rent a car without the underage penalty.

At one point Kim asked, “So how does it feel to be back in Arizona?”

“So nice to be out of New York for a bit.  The heat becomes too much”, I cracked as we stood in 105 degrees of dry Arizona summer, “and I don’t mean the weather.”

“Yes”, she agreed, “I don’t know how you do it.  Though I moved out to Arizona when I was young, I had drama by the age of thirteen; the year before I left NYC.  Girls that age should not be exposed to what we were at that age; makes us way too jaded.  Speaking of bad decisions, see anyone you like this evening?”

Mike and Charlie were cute.  I watched them for a moment and then settled my gaze on Charlie.  “Yes, I think I may have found one.”  Following my gaze, Kim agreed, “Fine choice.  Cute and I heard that he is great in the sack.”

I was in town for only five days and most of my visit followed the same daily schedule.  After a night of heavy collegiate level drinking we finally crawled out of our hotel room at noon-ish, ate breakfast, shopped, and drove around the beautiful desert towns (any of it beautiful and different to a New Yorker).

Saturday rolled around, which meant time for some ink.  Kim has a few good friends at Phoenix Tattoo Company, which is quite reputable.  They have inked some amazing pieced for Kim and I couldn’t wait for my new addition!  Kim sat first, having her name inscribed among blooming lotus blossoms on her outer thigh.  I was up next and chose something into which I invested a great deal of thought.  A large royal blue rose in full bloom with a smaller bud above on the same thick stem with a few words from my favorite Paradise Lost quote, “Abashed the Devil stood…saw and pined his loss”.  There is something about having a man tap ink into the skin of my outer thigh that inspires the most adventurous and reckless mood to rise from the depths of my soul.  As Kim and I agreed during the first night, “This feels like a long weekend of bad decisions.  Let’s embrace the debauchery.”  Right on, Sistah!

We picked up Charlie who came back to the hotel with us to pregame as we showered and prepared to go out.  After quite a few vodka and sodas and some silly, dorky photos starring Kim and me, we headed out to Tavern.  We met up with Mike, Cory, and a few other friends of Kim.  Yes, I felt like the oldest person at the bar, though I let go of this complex after a gin and tonic and two shots of Patron.  The guys volleyed for our attention and were extremely flirty.  After many cocktail/tequila shot combinations it was time to hit the road for some late night Mexican…food (not men).

Charlie, Mike, Cory, Kim, and I headed to Filiberto’s or Fili B’s as they like to call it.  Mike insisted that I sit in his lap on the way to Fili B’s.  I was not too keen about this, though didn’t give too much thought to it, as I was hungry and wanted our food fast. The entire ride to Fili B’s was a game of cat and mouse in the back seat.  Mike’s mouth was the cat and mine was the mouse.  Each time he came in for the kill I moved my head slightly to thwart his attempt and then saw what I wanted staring right back at me in the rearview mirror–Charlie.  Once at Fili B’s the boys ordered food and Kim and I sprinted to the bathroom for what else?  A girl’s chat session.

“Ok”, began Kim, “we must devise a plan.  Mike wants you.”

“But I want Charlie”, I replied, “Mike reminds me of your brother and ewww, that is creepy.  Been there, done that, bought the t-shirt.”

Kim looked at me and laughed, “Yes, though Mike doesn’t know it, that is the exact reason why I decline his advances every time he tries to get into my pants.  EWWWWWWWW, gross!  OK, I will make this work for you, Frankie.”

Leaving with our carne asada fries and burritos, we first dropped off Mike and Cory.  Charlie was our designated driver, therefore he was going to see us back to the hotel safely.  And Kim sat on Mike’s lap after leaving Fili B’s.  What a great friend!

Back at the hotel we three sat on the couch in the living room of our suite and inhaled our food.  As soon as Kim went into the bathroom, Charlie grabbed me.  Carne asada fries flew, as did my shirt, his shirt, my bra…”Ahem” I heard from behind me and pulled Charlie to my chest as I laughed.  “I am going to turn around AND close my eyes,” said Kim,”and you are going to run straight for the bedroom.  I will sleep on the couch. And you’re welcome”.  Did I mention that she is a great friend?

From this point in the tale my memory becomes a blur of skin, sweat, and yes, the one lone condom that I remember to keep in my purse.  Once we finished (yes, we; Kim was right, he was a great lay and considerate as well), he wanted to go again, though I turned to him and said (or gave a Patron produced mumble), “Do you have another condom?”, completely forgetting about Kim’s stash!!  To which he replied in the negative.  I looked at him and said, “Pity”, rolled over and fell asleep.  Hey I may have been drunk but no glove no love sweetie.

We woke the next morning and Charlie drew me close, saying, “Come on, I want you.  Now.”

“Oh fuck!”, I thought.  “Please don’t be angry”, I said as I pulled over the toiletries bag and pulled out a long sleeve of condoms.

Charlie gave me a look, rolled his eyes, pulled me close, and began seducing me all over again.  I think he was a bit annoyed, though too bad I don’t go raw with someone who does not rank as a serious boyfriend with whom I have a monogomous relationship.  Eventually, after we were dressed, Kim wandered into the room and sat for a chat.  She then was going to drive Charlie home, at which point the kid turned, playfully punched me in the shoulder and said, “Take it easy, see you later”.  What a strange goodbye…even for a 24 year old!

Apparently Kim noticed what she considered to be Charlie’s odd behavior.  We were both completely stumped.  Last night Charlie had offered his shower to me before I hopped the redeye to NYC tomorrow, as I would be checked out of the hotel by 11 am.  Kim and I enjoyed our final complete day together and took it easy; we did quite a bit of damage of these last few evenings.

The next day, she reached Charlie who was a bit unsociable over the telephone, though said that we could come over and use his shower.  At this point I didn’t care and only wanted to get onto the plane feeling clean and relaxed.  Charlie was totally distant toward both Kim and me.  I could see the confusion on Kim’s face.

Once I was in the bathroom it all made sense.  To my horror sitting on the toilet tank cover was all the explanation that I needed.  There it sat.   The douchebag bible…I Hope They Serve Beer In Hell.  Good grief, that explains it.  Anyone who takes cues from Tucker Max has to be disgusting.  EWWWWW…now I definitely need a shower.  These damn kids today! –Frankie

July 16, 2009 Posted by datedemall | Friendship, Hook-up, New York, Sex, Travel, Work, dating, economy, fuck buddy | , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , | No Comments Yet

Reading Too Far Into It?

dream Usually by this time of year, we have already enjoyed a few evenings spending a carefree after work happy hour at a rooftop bar somewhere in Manhattan. This rain, cloudy weather, and fog have not made such locales very appealing. The RD Partners crew was looking to have going away drinks for an associate who was accepted into the MBA program at Harvard. We became optimistic a few days ago, as the rain had subsided and the sun was now teasing us with a game of hide and seek. With high hopes we headed over to Dream Hotel’s Ava Lounge

I ordered my Tanqueray and Tonic when Kayla started in again about me staying with the firm.

“C’mon, Frankie; Eileen is not going to return from maternity leave and you fit so well within our firm.  Pllllllleeeeeeaaase don’t make me jump on the assistant search with a recruiting firm!”, she pleaded.

“You don’t want me working with you permanently.  I drink way too much during happy hour; it would be most beneficial to find an assistant who doesn’t drink as much”, I joked.

“Hellloo, that is one of the many reasons why you must stay!  It’s summer and we have much more happy hour bonding to do!”, cracked Kayla.

Yitzchak, a VP, asked, “Well what do you want to do?  Please don’t tell me that you are thinking of reentering publishing?  You will be committing career suicide!”

I saw that this was going to become a serious debate, though I must stand firm on my decision.  “I know where I belong.  If the industry is suffering, then what a great time to be involved.  The learning experience will be priceless”.

“I can respect that,”  said Cole as he walked up from behind me.

“Thanks, I appreciate it.  At least someone is on my side,” I joked.

“Well,” began Kayla as she looked from Cole to me and back again,”searching for a job within publishing isn’t the only thing that Frankie is up to.”

Everyone was sort of puzzled except me.  I thought, “Oh please, not in front of Cole.  Oh no, please don’t say it.”

“Frankie”, Kayla continued, “is already working on writing projects.  She writes a funny little dating blog.”

Oh yes, there it was.  She said it in front of the guy who I was crushing on.  Oh the red fire in my cheeks; why must I blush so deeply?!

“Oh really?”, “A…dating blog?”, “Tell us!” were the synchronized responses.

How should I approach this one?   Here I go, giving it a shot, “Well, yes, it is a joint venture with my roommate Ruby.  We chronicle our funny dating stories through a blog.  It is entertaining and, I will admit, therapeutic for Ruby and me”.

“That’s great.  Can we read it??”, asked Yitzchak.

“Yes, we want to read it!  That is cool”, added Cole

“Well, boys it is a bit risque.”, added Kayla.

Looking for a save, I said, “You may fire me after reading it and I can’t afford to lose my job right now without a lead, thanks!”

“On the contrary Frankie, we may promote you, if it’s that good of a read!”, chuckled Yitzchak.  He continued,”Try this whiskey.  It’s called Woodford Reserve and it is tasty.”

“No thanks,” I replied, “if I mix that with my Tanqueray, then we will all be sorry.  Whiskey and I are not very good friends.”  Though truthfully, I couldn’t help but think about how my crush now knows that I document my love life online.  I thought about how he wants to read me (well, the blog), which is a good sign, though I still can’t read him.  Yitzchak continued to push the whiskey, though I wanted no part of that action at all.    “Fine,  I don’t want your lips touching my glass anyway.  Considering you write a dating blog…who knows where those lips have been”, Yitzchak cracked.

“Well, at least I know my lips have much more fun than yours, you old, married coot!,” I retorted, laughing as I tapped his glass with mine and initiated a group toast.

Our group erupted into a loud, resounding, “WHOOOOOOOOOAA!!!!”, “Dude she got you good!”  I met Cole’s gaze as everyone stood enjoying the respite from the dreary weather.  I held those captivating blue eyes, that were now beginning to read me.

June 19, 2009 Posted by datedemall | Friendship, Interoffice Dating, New York, Sex, Work, dating, economy, relationships, roommates | , , , , , , , , , , , , , , , , , , , , , , , , , , , , | No Comments Yet

To ASSociate or Not to ASSociate…

On this evening marking  Barack Obama’s 100th day as president, I sit in my bedroom on my laptop looking back on my first nine days since setting my life back on track. I have no one to nurse, no one to worry about comforting, no one, that is except for myself.  This is my show…working with the hand that I have been dealt; which is much better than Barack Obama’s.  I have a job, an apartment, the most supportive friends;  I have a life.

The girls at RD Capital Partners welcomed me back and filled me in on the most recent firm gossip over lunch at Chopt.  Which VP was now married and may begin a family soon.  Which member of the accounting team became so drunk at last year’s RD Capital Team Conference that she fell into the bonfire; and then attempted to pick up one of the hot associates.  Oh, yes, and speaking of that particular associate, he was looking quite tasty according to Sarah and Kayla.

“Yes, Frankie you missed a bit.  I know you were a taken woman when you last worked with us, though Cole is now single as well”, smiled Kayla.

Cole was a cute, young associate who had mesmerizing blue eyes and golden blond hair, which was cut perfectly short.  Though I would serve as the assistant to a principal, another associate, and Cole, I had not yet seen this cutie.

“Why haven’t either of you chased him then?”, I asked.

“Well, I have my own guy who has been on my mind; actually I would like to ask you what you think.  I met a hot Aussie, which we must discuss…though after filling you in on Cole.”, said Kayla

“Yes, and well, I don’t date colleagues,”  Sarah chimed in.

“Ah, what a coincidence,” I began, ” neither do I.  He sits four offices down from my cubicle and if I am supporting him as his assistant, I can’t, well, you know…ahem…support him, um, in other ways.  We all remember what happened to those kids at the advertising agency, now don’t we?”, I said; barely finishing the sentence before busting out laughing.

“Stop that!”, pleaded Kayla, “We should make a pact so no one dies from choking on our food while eating and sharing funny stories.  Breathe, chew, swallow, speak.”

Sarah and I looked at each other and couldn’t help busting out laughing.  “Oh you are both perverts!”, yelled Kayla.

“We didn’t say anything, though you are obviously right down in the mental gutter playing with us!”, I accused,”Let it rain!”

Back at the ranch, er, office, sitting at my desk, I heard Sarah greet Cole, as he walked in.  He looked around the corner and saw me and asked,”Hey Frankie!  How are you?”

If the financial sector was suffering, then you wouldn’t know it by looking at him.  He looked different.  Same features, though much more attractive.  Much more…manly.  It may sound cliche, though was he working out more often?  He looked like he should be sailing on The Cape and spending summers at The Vineyard.  I could have ripped him from a Polo advertisement.  If  Helen launched one thousand ships, then Cole could certainly save the economy.

Kayla was watching from her cube, located next to me, and grinning to herself pretending to work on a partner’s itinerary.

“Great to have you back, Frankie,” continued Cole.

“Happy to be here, Cole,” I replied,”Quite fortunate actually.  Need help with anything?”

“No, I’m all set.  Thank you.”

I took him in for a moment longer than one should.

“Excellent,” I snapped out of it,”Well, let me know if you need anything at all.”

“Will do, thanks”, replied Cole, walking away with a smile that could light Times Square, and the bridges, tunnels…yes, you get it.

“Well you are a darker shade of scarlet, Frankie!”, observed Kayla.

“It’s the Irish skin…Kayla O’Rourke; you should be quite familiar with its tendency to burn,” I replied defensively and took a sip of my mango nectar.

“HMMMM,” thought Kayla”,…I wonder if Cole burns.  You know, last year Mack (a partner) held a barbecue at his home.  Cole looked smashing in his swim trunks…”

I spit out the tasty beverage and coughed furiously, as mango nectar shot out of my nose, “The rules still apply!!!!!!”, laughing.

No, this deal is definitely not bad…not bad at all. –Frankie

April 30, 2009 Posted by datedemall | Friendship, Interoffice Dating, New York, Politics, Sex, Work, dating, economy, relationships | , , , , , , , , , , , , , , , , , , , , , , , , , , , | No Comments Yet

Did He Use the R-Word??

Time to buckle down. My savings is dwindling, it’s April 15, and I am hoping for The Fed to step in and save my inheritance; well TARP or the New York Lottery ($109 million?!??!?!). I definitely have a better shot at winning the lottery than relying on any government agency.

I am trying to find a job at a time when landing a job is a far greater feat than finding Jimmy Hoffa. And finding a job within publishing?   A move to the financial sector would probably be a better career choice!

My eyes feel like they are bleeding as I search Mediabistro and Monster.  After digging through STUFF in my apartment, I find my business card holder.  SCORE!!  Why am I excited?  Here I am sitting on my living room floor, various versions of my resume and cover letter scattered everywhere.  Another unfortunate soul added to the unbelievable number of unemployed New Yorkers.  “Yea, good luck Frankie,” I say to myself sarcastically.

Picking up my phone to ring my first and most helpful recruiter, I am shocked as it rings.  No name, though a familiar number, though not sure who it…hmmm…oh what the hell; I’m bored.

“Hello?”, I said

“Hey Sexy, how have you been?”, said the unmistakable voice of Adam

I giggled a bit, “I am…”, I thought about it for a minute, “I am OK; hanging in there.”, I responded. “Yes, tough times right now”, he added.  We chatted for about 20 minutes, which was strange considering our history.

Adam finally asked, “Frankie, I just returned from tour in Europe; would you mind if I came over?”

“Adam, I am not really in the mood.”  I had to admit, I was so, very, VERY sexually frustrated that the PETA people were going to be on my tail citing animal cruelty against my Rabbit.  Though, Adam no longer did it for me.  Sure, you can never truly know if a partner is telling the truth about their history however, having received an invitation to the bacchanalia changed my entire opinion regarding sex with Adam.

“Well, Frankie”, he began,  “I wanted to discuss something.  You are so easy to talk to and great to hang out with and I was wondering if you would…possibly…considering trying to move our relationship to another level?”

Adam never ceases to amaze me.  Is he for real?  “Are you for real?”, I asked without thinking.  I sounded like a complete asshole.

“What?  Oh, thanks, Frankie, that was kind of shitty”, he said, sounding hurt.

“I apologize, I did not mean to say it the way it sounded.  I am flattered, Adam, really, though I can never look at you as anything other than (this would be the perfect moment to save myself from that last emasculating jab)…my great lover who always came through and delivered in my time of need.”

“Well, fine that will do,” he said, “And uh, perhaps you have some single friends?”

“EWWWWW, you are gross; we are not into sloppy seconds ’round here,” I replied, while laughing. We ended our conversation, still as friends, though definitely no longer lovers.

Finally, I picked up the phone and contacted the recruiter.  She was pleasantly surprised to hear from me and sympathetic for my current situation.

“Linda, I will even take something in finance, I don’t need to return to publishing just yet,” I informed the perky little woman on the other end.

“So strange, though great news!  RD Capital Partners has an opening for an executive assistant; one of their girls is taking maternity leave–this could turn into a permanent position and great pay–$25/hour!  What do you say?  They always ask if you are on the market again and absolutely love you!”

I worked for the firm a few years ago while on the job hunt before I landed my last position.  What a great team to work with each day; I was in!  “Linda, I would love to!”

Sorry Adam, seems like some of us are gettin’ lucky today!–Frankie

April 16, 2009 Posted by datedemall | Friendship, New York, Sex, Travel, Work, boyfriend, dating, economy, fuck buddy, girlfriend, relationships | , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , | No Comments Yet