From Menage a Trois to Dinner for Two

Reminiscing about my near hook-up with a much younger, shorter man last week got me thinking about my experience with someone from the opposite end of the spectrum—a distinguished, financially stable, forty-something divorcee with his own real estate company and a seven-year-old son. Although I had written off dads in the past, I decided that if I was going to become a stepmother, I might as well do it with a successful businessman who lived in mid-town rather than an ass-smacking, dirty-talking teacher from Brooklyn…

It was a Friday night during happy hour and, as usual, I was behind the bar slinging Coors Lights and whiskey-cokes to under-tipping Mad River patrons. I was having an exceptionally good hair and cleavage day and was looking forward to my shift’s end so that I could head to The East End for a few drinks with Jenny Saurs. As I was serving yet another draft beer in a plastic cup, an attractive man in a business suit sauntered up to the bar and ordered an Amstel Light, a Ketel One and soda, and two shots of Patron. He was clearly not the typical Mad River customer in terms of age, income, or quality of clothing. He reminded me of Jeremy Piven and stood with confidence and cockiness, two of my favorite qualities in a man. He had piercing blue eyes, which I could feel looking me up and down as I bent over to get his beer from the cooler.

As he handed me his Amex, he looked straight into my eyes and said with all seriousness, “I’m looking for a third.”

I paused before responding, wondering if my thought process was on the same path as his. Was he looking for a third shot of Patron? A third teammate for a hot game of Pictionary later? But with the way he was intently watching me, waiting for my response, I was almost certain that my dirty mind was on the same page as his dirty mind.

“A third, as in a third for a threesome?” I asked, holding his stare.

He ignored my question and looked me up and down again. While he was so intently surveying my assets, an attractive, dark-haired woman in her late thirties saddled up to the bar next to Jeremy and began to stare at me as well.

“Are you interested?” Jeremy coolly asked.

“Obviously.” I evenly replied and I walked to the other end of the bar to serve another customer. I had never been involved in a threesome before and was quite flattered to be asked by this attractive and seemingly sophisticated couple. The last time I had been asked was by a drug dealer and his third cousin’s uncle’s niece. I knew that I didn’t want to participate then or now, especially this sober, but there was something about Jeremy that I wasn’t ready to walk away from, so I kept up my act.

I glanced toward the end of the bar where Jeremy and his number two lady were standing, only to find them staring right back at me. I quickly scribbled down my number and walked back towards them.

“One question. Are you two married?” I asked Jeremy very matter-of-factly, without even bothering to look at Number Two.

Clearly this was a typical question asked by any threesome veteran and I wanted to appear as if this wasn’t my first ménage a trois. Plus, I sure as hell didn’t want to be dragged into a messy divorce down the road where I would be fighting with Number Two for Jeremy’s house in East Hampton when he decided to leave her because he had fallen madly in love with me.

Jeremy finally cracked a smile as he answered no and Number Two scowled and walked away. I was very glad that I was not going to have to encounter her in the bedroom later, as she seemed incredibly needy and attention starved. Jeremy and I said our goodbyes so he could chase down Number Two and he promised to call me later that night to “set something up.” While I wasn’t planning on seeing him ever again, I would at least be able to Internet stalk him since I had noted his last name and company from the credit card he had used to pay for his pre-threesome drinks.

Less than five minutes later I had a text from Jeremy, in which he broke the news to me that the threesome was off because Number Two didn’t like how Jeremy and I had been looking at each other. After gloating to myself for my dead-on judgment about Number Two, I broke the news to Jeremy that I had never been interested in a threesome from the start. Luckily, rather than responding with an angry text deeming me a whorish tease, he replied with: Interested in just me? ;+)

Who knew just how interested I would end up being come Monday at our dinner for two…

Sex & the UES: 57 Inches

While spending a lazy Saturday in bed recovering from Friday night’s debauchery and late-night mac ‘n’ cheese party, I found myself watching two movies about women dating and/or sleeping with younger men. The first movie I watched was The Reader, a critically acclaimed movie with full frontal male nudity, which in my opinion, always adds to the quality and entertainment level of any cinematic presentation. The second movie I watched was I Could Never Be Your Woman, a romantic comedy that went straight to DVD and was free On Demand. Dating younger men is becoming a more acceptable social norm as we watch such movies and read Ashton’s constant Tweets about Demi—so why didn’t my experience with a younger man go as well as these Hollywood relationships? It ended up having nothing to do with age…

It was another Friday night at Mad River and I was wrapping up my bartending shift as a group of guys settled in at the bar. A blonde, Prince Harry-look-alike caught my eye and started chatting me up. After a few shots of Jameson I decided to join him on the other side of the bar, so I pulled up a stool for a few drinks. Three Bud Lights and some basic, ice-breaker questions later, I learned that Harry had just completed his junior year of college and was visiting his older brother, who lived on the UES, for the weekend. He was fascinated by my city-living, bar-hopping, sex-blogging lifestyle and was undoubtedly unconcerned that I was a good five years older, more mature and more financially stable than his keg-standing, class-skipping, cold-pizza-for-breakfast, frat boy self.

After increasing our blood alcohol levels to approximately twice the legal limit, we decided to head back to my place for a little late-night romp around. I stood up, slipped on my jacket, grabbed my purse and waited for Harry to follow suit. I knew he had been drinking for a few hours, but I hadn’t realized he was so intoxicated that he couldn’t get up off of his bar stool. But then he looked at me and said “Let’s do this.” I looked down only to realize he was standing—standing a good four inches below me when I wasn’t even wearing heels. I had seen this exact scenario on an episode of Sex & the City, but had never fathomed it would happen to me in real life.

I began to panic—little did Harry know that I had a fear of midgets and he was teetering between the classification of a small person and a leprechaun. But it was too late for me to revoke my invitation and before I knew it we were in a cab on the way to my apartment. Thankfully, my roommate was not home to witness this circus debacle that was taking place and I immediately beelined for my room, my mind racing on how to get this little man out of my love shack. My mind immediately went to Betsy, one of my girlfriends who I was supposed to meet for drinks after my shift. By now she had probably already taken at least seven shots of So-Co Lime, but I hoped with all of the optimism that I could muster in the company of a midget that she could help me to get out of this mess.

Harry sat down on my bed, waiting for me to make a move. Instead of me cozying up next to him, I slyly took my cell phone out of my purse and excused myself to the restroom. I frantically texted Betsy, instructing her to call me within the next two minutes and give me a dramatic reason of why I would need to immediately rush down to Murray Hill to attend to her intoxicated ass. I camped out in the bathroom for another ninety seconds, willing Betsy to pull through and call. Unfortunately for me, Betsy failed to communicate in any way, shape or form, and I was forced to come up with a new exit strategy.

I took a deep breath and headed back into my room where Harry had made himself at home—he was lounging on my bed watching Sportscenter, with his shirt off and folded neatly on my dresser.

“Oh, I see you figured out how to turn on my TV.” I commented, somewhat inhospitably.

Before Harry could respond, I hurriedly said, “I’ve got some bad news. I was supposed to meet my friend Betsy for drinks after my shift and now she is waiting for me downtown. She is really drunk and just punched a guy in the face, so I need to make sure she gets home safely.”

“Well, I can come with you.” Harry quickly volunteered.

“No!” I replied with panic.

“I mean, no, you don’t have to do that. Why don’t you just head back to Mad River and drink with your friends until I finish up with Betsy.” I suggested as I handed him his shirt.

Once Harry redressed himself and turned off Sportscenter, we headed outside and he hailed me a cab. I gave him a kiss on the cheek and promised I would call him later. As I waved goodbye from the backseat, I told the cab driver to take me to 92nd and First.

“But miss, we are on 95th and First.” he replied with confusion.

“You want tipped or not?” I asked, in which he responded with stepping on the gas.

After my short cab ride around the block, I stopped at my favorite late-night bodegda for a snack and headed home to watch Oprah. I never met up with Betsy, who ended up grabbing a complete stranger’s crotch and eating an entire pizza that night. And I most certainly never met up with Harry in his 57-inch glory at Mad River—how could I when Oprah was interviewing meth addicts?

In You Doesn't Always Mean Into You

After spending a dreary Saturday in bed drinking wine and catching up on Denise Richards: Its Complicated, I decided that I should improve my entertainment standards and watch something with actual acting involved. After failing to find a Law & Order re-run, I decided to watch He’s Just Not That Into You. While it showcased a star-studded cast of actors intelligent enough to not procreate with Charlie Sheen, it also depicted just how desperate and pathetic single women can be. Although I have been guilty of tracking down a crush at the library after drinking a bottle of gin in college, occasional Facebook stalking, and a lot of drunken texting, I have yet to stoop to the embarrassing level of desperation that Ginnifer Goodwin’s character did in her quest for love. But why do so many women stoop to such a desperate low?

The movie left me not only wondering why women are often so despairingly consumed with finding true love, but also wanting to hear a man’s perspective on the dating world, so I met up with my single friend Jimmy Whisk for some afternoon Bloody Marys at Wicker Park. As the general manager of a popular Upper East Side bar, Jimmy pulls almost as much tail as Bret Michaels, sans a bandana or a bus. Apparently a pink polo and the words “I’ll definitely get you a bartending shift” have become an instant panty dropper for young, drunk girls barhopping in Manhattan.

Here is some insight into a single man’s mind—listen up, ladies:

Potential Girlfriend vs. Booty Call
How can you tell the difference whether you’re prospective dating material or just a one-time hook-up? According to Jimmy, if he tries to go all the way the first time, then he isn’t thinking about taking you home to mom. If he’s interested, he’ll be willing to wait and respectful enough to keep it PG-13 until at least the third date.

Dealbreakers: Bad Breath & Lingerers
While bad breath should be completely avoidable in today’s day and age of Altoids, tongue scrapers, and electric toothbrushes, halitosis is enough kill the mood or even morning wood. Excessive drinking and late night pizza never help the cause, so avoid the garlic knots and swish with some vodka before leaving the bar.

As for lingerers, if he’s not taking you to brunch or serving you breakfast in bed the morning after, it’s time for you head home. When he starts making excuses, such as “I hate to do this, but I need to head to work.” and it happens to be Sunday, you’ve overstayed you welcome and its likely you won’t be invited back.

Words of wisdom from Jimmy, “When a girl leaves early in the morning without me having to ask, it’s like getting something for Christmas that you didn’t even know you wanted.”

The Reverse Effect
So you have a drunken hook-up and wonder if it will eventually lead to a blissful relationship. You’re pretty, smart, and funny, plus you had great sex last night, so why wouldn’t he want to see you again? Unfortunately for any optimistic ladies out there, seldom does a one-night stand turn into anything more. While a relationship leads to sex, sex doesn’t necessarily lead to a relationship. Move on.

He’s Not Interested
More often than not, women fail to get the hint only because they don’t want to. It’s much easier to hope he’s going to call—or email or text or Facebook poke you—than admitting defeat. According to Jimmy, a guy is never going to have the consideration or the balls to be honest with a girl and simply tell her that he isn’t interested when it takes much less effort to simply avoid all communication or act like you lost your cell phone.

While the female population should not lose total hope when it comes to finding true love, or at least a suitable boyfriend, my afternoon with Jimmy Whisk gave me a much-needed reminder that men are often selfish and lazy. So in your quest for a man that will take you on a proper date and buy you breakfast the next morning, keep your pants on and be on the lookout for the Jimmy Whisks of the world lurking in a bar near you.

Dealbreakers

We all have certain standards when it comes to dating—standards far higher than those upheld to a drunken one-night stand or a go-to weekday booty call. Dating standards typically center around basic criteria such as family values, a sense of humor, a college education, and a good job. But in the beginning stages of a relationship, when your energy is focused on the excitement and fun of a new person, it is all too easy to overlook, or even completely miss, certain details that should be blatant red flags, or what I like to call, dealbreakers. Read on for the top deal breakers in my book:

An unhealthy obsession or even a passionate like of anything Science Fiction. If your man talks about the cast of Battlestar Gallactica as if they’re his personal friends or has ever attended a Star Wars convention, he probably has a few other peculiar interests that will eventually come to light. And if he lives in his mother’s basement, there’s good chance he will remain there with his Jedi warrior figurine collection for the remainder of his adult life.

Ownership of anything spandex. Spandex is a material that should rarely be worn by anyone, let alone a heterosexual male. Singlets, Speedos, and biking shorts should only be found in the drawers of cross-dressers who frequent Splash on Friday nights or award-winning athletes. Even if he bikes in Central Park every weekend or is training for a Triathlon in July, he can do so in a pair of mesh shorts and a cotton t-shirt.

Cats. Although I happen to be severely allergic to cats, their life-threatening dander is not why they made my dealbreaker list. Cats are inherently creepy, always lurking and constantly judging with their penetrating stares. I don’t need my bedroom moves critiqued by some furry animal that gets off on paw licking and catnip, let alone a boyfriend who shares his apartment with such a creature. Get a pet that can fetch.

Reliance on his mother. Whether it’s for everyday, routine errands or menial tasks such as picking up and dropping off of dry cleaning, depositing money in the bank, replacing toiletries/personal grooming products, or cooking every single meal he eats, he needs to cut the cord. If he hasn’t learned how to take care of himself by now, he will just rely on you in the future instead of his mother.

Cartoon character tattoos. These either signify gang connections from the mid-nineties or an unwillingness to let go of his childhood and/or trailer park. No further explanation needed.

Excessive movie quoting. Everyone loves a good movie quote here and there, but if it’s your beau’s main lifeline for upholding a conversation in a social setting, you’ve got a long, awkward road ahead of you when it comes to company Christmas parties and happy hour with your friends. People will notice and will thus judge.

Children. Everyone makes mistakes and some people’s come out of wedlock in the form of a small, talking nugget that calls your man “Daddy.” If you’re not ready to change diapers, attend school plays and deal with baby-mama-drama, then you’re not ready to become a step-mother. Dating a dad is no easy task—be ready to receive at least 45-55% less attention and fewer presents than you would from a non-dad. Harsh, you say? Cold, hard reality, I say. Go ahead and judge me, but it’s still a dealbreaker in my book.