Playboys

The idea of the playboy has been around for a very long time (just look at single again senior bachelor Hugh Hefner). The phenomenon can also been seen weekly on TV shows like MadMen and Entourage and in new movies like The The Hangover and not so new movies such as Bachelor Party. The theme of a day in the life of a playboy would feature the following: booze, babes, and bad behavior. But outside of the bunny mansion and popular mass media, do playboys really exist? I am sorry to report that playboys, real playboys are alive and kicking. And in New York, where there continue to be a plethora of men working in the still male-dominated world of finance and plenty of other hound dogs working in other fields too, playboys abound.

Robby was quite cute with his crew cut (think Tom Cruise in Top Gun), dimples, and dashing blue eyes. He worked in finance and had some tales to tell – drinks with clients where he was told to chat up women and buy them drinks so that the women would spend time with the clients and numerous trips to strip clubs with said clients. Then there was the office gossip about Robby’s bosses and their numerous affairs and bad-boy behavior. So when I decided to accompany Robby to a work event, he gave me fair warning that things might get rowdy. In anticipation of too much imbibing, the company would be sending a limo to drive us to and from the event. I have to admit I was curious about seeing his coworkers with their respective wives and girlfriends and wondered if their inner playboys would surface or not.

We were given champagne before we even shed our coats. We mingled and as Robby introduced me to his colleagues, I could feel them checking me and Robby’s new titanium watch out. They asked me loads of questions – most specifically how had Robby managed to meet someone exotic looking like me (yes, this was the exact phrase used) and what did I like to do for fun (which made me feel kind of like a bunny must feel when she rattles off her likes and dislikes).

As we sat down to dinner, conversation turned to Robby’s new BMW, cars being a favorite topic among the group. Robby’s boss was visibly impressed with the car talk and with a twinkle in his eye asked me if I had come with the new car. Thanks to the alcohol, I managed to laugh at his joke but couldn’t quite shake the creepy idea of being seen as some kind of trophy Vanna White. Though Robby liked to maintain he was different than the guys he worked with, he didn’t say a word during the exchange.

As the night wore on, Robby whispered sweet nothings about his colleagues in my ears. He was quick to point out who was sleeping with whom (including one of his married bosses in attendance with his wife /high school sweetheart who had been for years having an affair on the side with the head secretary). Yes, he used the word secretary. He gossiped about drug usage, rampant alcoholism, problem children and illegitimate children. Then, Robby told me about his best buddy at work whose wife and he had recently decided to have an open marriage. I tried not to keep my look of horror at bay but couldn’t quite manage as my eyes came to rest on the nice couple I had met when we arrived. And here I thought they were the most normal people at the party!

By the time the night ended, I realized that in Robby’s playboy world women, like flashy cars and the right watch, were seen as accessories. And while it might be fun to play spy, staying for any greater length of time would likely require a lobotomy. I like having thoughts and a voice far too much to give up my brain.

Speed Racer

Between the tortoise and the hare, I have always secretly identified with the tortoise. First, turtles are cute with their ambling gait and often artsy green features. Second, they are tough and resilient with their hard shells. Third, they are smart and know when to just slow down and take things easy. This last point is one that I sorely wish more daters would take –especially men who happen to live in Manhattan.

I know, I know, this city is fast and crazy and the speed of it all can make you dizzy. I suppose this is why I crave quiet and stability as much as I crave a good martini. One thing that irks to me to no end though is the men out there who treat dating (and everything that goes along with it) like one great race. When I meet a speed racing boy, I can’t help but wonder – What’s the hurry? Why the rush? And, can’t we just slow down?

Tom seemed like a sweet guy through e-mail and by phone. We had been exchanging witty e-mails for a couple of weeks and had had a couple of phone conversations that included laughter. So, I was eager to meet him. He suggested drinks after work, which seemed perfect – enough time to get to know each other but not too long just in case we didn’t click. Then, with our drink date set for the following week, Tom changed course and asked about meeting over the weekend for dinner and a movie.

In datespeak, the dinner and movie combo is a real date that would have us spending hours together. Hmmmm, if we didn’t click we would be stuck together for a stretch of agonizing time that would have me running lists in my head of all of the things that I would rather be doing – cleaning the bathroom (which I detest), brushing my dog (who likes to ‘play’ bite me with each stroke), reading The Corrections (which has been a doorstop in my place for many years). With this in mind, I gently let Tom know that I already had plans for the weekend but that drinks still sounded good. And yes, this was a smart decision because we didn’t really click over drinks.

Barry and I had a super time on first date (mojitos in a funky little bar). He was cute, funny, and came across quite dashing with his British accent (yes, accents can be intriguing). When he suggested steak and wine for our second date, I found myself looking forward to getting to know him better and to having a yummy rib eye to boot.

As snow rapidly fell the night of date two, I would not be deterred and arrived a few minutes late and wet to the bone. Wine helped warm me up and soon he was charming me with tales of growing up in England. He didn’t have anything planned beyond dinner so afterwards we just kept moving from place to place for drinks to keep warm. I found it odd that he kept asking me where to go next but liked the idea of braving the night with him.

Eventually, after about six hours together, the weather had worn me out and I was ready to call it a night. As we stood in the snowy street trying to hail a cab for me, Barry boldly told me that he would like to come home with me. Excuse me? We had shared a rather chaste kiss at the end of our first date and hadn’t broached any big topics, so his directness had me reeling. I politely let him know that this wasn’t really my style and that was the end of Barry.

I have to say that I’m not a fan of rushing to the finish line – any finish line. Call me old fashioned, but I quite like the idea of just having good conversations and getting to know someone. I suppose that this goes against the grain in our very fast-paced, over-teched world. Despite this, I will embrace the turtle in me and just try to remember that slow and steady wins the race in the end.

Hanging Out Vs Dating

I’ll admit, I’m a bit confused about this whole hanging out vs. dating stuff. I adore chillaxing with my girlfriends. We order pizza, drink wine, watch cheesy movies. We catch up on each other’s lives, we gossip about celebrities, we plan future get-togethers. I also like spending time out with a big group of friends (guys and gals) at a bar, to see a movie, to have dinner. But, in speaking with friends, it would seem that hanging out and dating are two different things. So what’s a gal to do when a guy she *likes* wants to hang out? Is ‘hanging out’ ever secretly code for dating? Is ‘hanging out’ with a boyfriend different from ‘hanging out’ with a new guy? I look to my dating past and to the advice of my friends to answer these perplexing questions.

On my second date with Jeremy, we went for Mexican food and Coronas. It was delicious and we both had a good time. Afterwards, he grabbed my hand as we walked along the sidewalk. Things were going well enough that I was open to having a third date with him. When we reached the subway stop, he mentioned that his brother was having a party over the weekend but that if there was any time leftover he’d call me so that we could hang out. Then he leaned over and kissed me. I got onto the subway in a daze – wondering what had just happened. Why had he mentioned a party and not invited me? I had flashbacks to my college days when boys wanted to hang out (ahem, hook up) with girls. Later as I went through the play-by-play of our date with friends they all pretty much agreed that this was not such a good sign. It seems when you reach a certain age, having a guy say that he wants to hang out is the equivalent to receiving the friends speech.

I met Jed through friends. He was cute, funny, and loved to frequent bars. He also loved to flirt and flatter until I was a blushing mess. We texted and e-mailed for weeks and then one rainy night, he invited me to meet him. Amidst too many drinks, he kissed me and the kissing didn’t stop until the bar closed. Despite the fact that his friends were there, he spent pretty much the entire night chatting with me. I’ll admit, it felt kind of like a date. I liked Jed and wondered if our hanging out would perhaps lead to real date sans friends. As we parted, he mumbled that we should “talk soon”, and I held onto these two words with a bit of hope. We exchanged a couple more texts but nothing ever came to fruition. In retrospect, it would seem that if a guy desires to go on a date he will step up and put it out there. He won’t say something like, “Hey baby, come meet me and my friends at this bar.” I might be cringing a bit as I write this, but at least I’m learning!

Back when I first starting seeing my past boyfriend Steve we went on many 1:1 dates – dinner, movies, live music, walks about the city. It was all so romantic. After we had been dating for awhile, we started doing things with our friends. He met my pals at a Depeche Mode concert, I played pool (badly) with his friends at a hip Brooklyn bar. We hung out with our respective friends on a pretty regular basis. In addition to this, we also settled into a routine of spending part of our weekends just hanging at home talking, watching movies, or cooking together. So, it would seem that going from dating to hanging out is a good, acceptable, even natural step when one has a boyfriend.

One of my friends recently reminded me that the bottom line is to have fun. While I do get her point, I suppose it depends on what a girl wants. And I can say for myself that somewhere between going to keggers and getting a real job, the allure of hanging out has lost a bit of its luster. And there is much to be said for an honest to goodness date.

Pretty Boys

When I was growing up, I had a crush on a boy named Luke. He was blonde with big blue eyes and eyelashes so long that I swear I could feel a breeze when he blinked. This was in the midst of Star War craziness, so of course we girls couldn’t help but think of him as Luke Skywalker’s doppelganger. His hair was slightly wavy and long, and as he fought with “Darth Vader” during recess, my friends and I would watch and sigh. We all desperately wanted to be his Princess Leia. There was something about him, with his defined cheekbones and full lips, that was almost delicately pretty. He was a pretty boy, and we pre-pubescent girls couldn’t get enough of him.

This was only the first of many such crushes I went through – other pretty boy longings included the lead singer from Ah Ha, singing “Take On Me” with eyeliner firmly in place, Eric Stoltz and Andrew McCarthy as they pined after their leading ladies in their respective John Hughes films, and Knight Rider David Hasselhoff with his magical car Kitt. The pretty boys were ,well, so pretty it was hard for me to take my eyes off of them. But, in the back of my head, I always wondered “Does it take him longer to get ready than me?” and “I wish I could get my eyeliner to look like his!” While crushing on a pretty boy seems almost a rite of passage for female teens and tweens (just think about the success of those boy bands), the grownup pretty boy is not quite so cute or endearing.

Taylor liked to compare himself to Elvis (a pretty boy if there ever was one) in everything – looks, moves, his appearance. He spent hours on this, primping and preening, and no, he was not an Elvis impersonator (although this really could have been his calling). He spent so much time in the bathroom that he answered his phone in there (seriously). When we dated, I marveled at his penchant for upkeep that rivaled only someone along the lines of, say, Ivana Trump. He was fascinated with his looks, and this made him fascinating to me – but not as a potential dating partner. He became a train-wreck I couldn’t turn away from, an experiment result worth waiting for. But the day I noticed my makeup in disarray and a ring around his collar, I knew it was time to say goodbye to him.

While on a flight abroad, I had the luck of sitting next to a male model. A real, bona fide, male model (think Zoolander). He was tall and exotic and really stunning. His eyes slanted alluringly, his shoulders looked as if they were padded, and his cheekbones were sharp enough to cut something. I was more than a bit surprised when he began flirting with me, but knew it was a once in a lifetime opportunity that I couldn’t pass up. Turns out he was on his way to Paris for a month of back-to-back jobs. He showed me his portfolio via his iPhone and asked for feedback on how to pose his glorious body, what I thought of his sixpack, if I liked him better with short hair or long. I answered his queries with ease. We were interrupted only by the stewardess eyeing him like candy and saying, “Can I get you anything, baby?” I swear, I’m not making this up! He shrugged his massive shoulders and declined food; after all, he was on a serious calorie-restricted diet. He had lost sixty pounds to become a model and gave me his brownie so it wouldn’t tempt him. As we exited the plane, the crowds parted for us in a way I haven’t experienced since I happened to see fellow pretty boy Ralph Fiennes on a midtown sidewalk.

In the midst of this star treatment, I realized that grownup pretty boys are a lot like animals in a zoo. They are quite fun to visit in the cages that they have chosen to inhabit, but I have no desire to take them home and to attempt to raise them outside of their preferred captivity.