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.

Wedding Moments

The romance, the celebration, the leap of faith being taken– there is something about weddings that forces us to ponder things and to take stock of our lives. If one is single and attending stag, it reminds one ever-so-much that one is not part of a couple. Perhaps this is why weddings seem such a good place to meet people, and why there are endless tales of romances that start over champagne and shared bites of someone else’s frothy white cake. At the same time, for people who are attending with a date, it can force both parties to examine their relationship in a new light. Are we serious? Where is this going? Do I desire marriage? Would I even want to put a ring on this guy? And sometimes, for a couple, the fallout from attending (or not attending) a wedding provides answers that may not be so welcome.

I had been dating Steve for about nine months. We were having fun. He was a breath of fresh air, his very chillaxed attitude contrasting with my type-A personality. He calmed me down, and I felt like we served as a kind of yin and yang for each other. When a good friend sent me a wedding invitation to her upcoming nuptials, for once the invitation came with someone else’s name on it besides my own. We decided to make a weekend out of it, driving up to Vermont amidst gorgeous fall foliage and staying at a quaint B&B. The wedding itself was perfection. But, in the midst of the weekend, I realized that Steve was not someone I could envision having a monumental relationship with. It saddened me. I liked Steve for so many reasons - he was a light-hearted guy, a thrill-seeker who encouraged me to be more spontaneous, and there was something very nice about our familiarity.

Several months later, Steve and I attended the wedding of two of his close friends. They were lovely people, and we had a great time. He whirled me around the dance floor to some fun eighties tunes. We indulged in too many drinks and too much cake. To everyone around us, we probably looked like a happy couple. But again, I found myself thinking about our relationship and knowing, deep in my heart, that we were not suited for each other for anything beyond dating. When things ended a couple of months later, it didn’t come as a surprise, but rather felt like the ending I knew was going to happen all along.

Then there was Clay, a guy who on one of our early dates mentioned an upcoming wedding that would be fun to take me to. Naturally, with this wedding date looming in the future, I pondered what I would wear, how I would do my hair, if I needed to buy new shoes. As the date drew near, Clay hemmed and hawed and said that he wasn’t sure he wanted to take me. *Note to men –never mention a wedding to someone you are dating unless you plan to take them!* He didn’t want me to feel overwhelmed by meeting all of his friends at once, and he was afraid I would feel abandoned if he stepped away to chat with them. On one hand, I could see his point of view. It might indeed be a bit much to meet so many people at one time, and I didn’t much like the idea of being abandoned either. On the other hand, a little warning bell went off in my head – wouldn’t a guy who was really into me want me to be his date and meet his friends? As the wedding grew near, I couldn’t seem to make peace with the idea that my boyfriend would rather go stag than take me as his date. Predictably, things didn’t work out with Clay.

Like it or not, these wedding moments have a way of forcing things to a head. And I’ve begun to think this might actually be a good thing. After all, discovering that a guy is Mr. Wrong is a step in the right direction. It clears the way for Mr. Better, Mr. Right, or perhaps even allows one to revel in singledom just a little bit.

Playing Games

I’ve never been very good at playing games. And no, I’m not talking about the mental, mind-grueling, wait three days before calling, don’t pick up the phone on the first ring, wait until he opens the car door kind of games. I’m talking about anything that involves moveable pieces, joy sticks or the like, balls, and using any of my limbs. Yes, there are a few games that I’m not terrible at like Yahtzee, pinball machines, and Clue (to my family, again, I swear I’ve never, ever cheated, I’m just gifted!). But, usually, I’m so bad that it’s kind of embarrassing. I try, I have no problem trying. I should get major points for trying. But I fail often and badly, which leads to much unintended, slap-stick humor for my dates.

Back in the day, I used to play darts when I would go out with my friends. I was truly terrible. I often hit the wall. More than once I broke darts this way. My aim was not good and people were fearful they would lose an eye. I only got worse when I had a drink. So, when Collin suggested darts in the midst of beers, I politely tried to dissuade him. “Really, I shouldn’t”, I said demurely. He mistook this for flirtation and a desire to dart and we were soon lined up in front of the bullseye. My first two attempts hit the wall. People moved away from us. Collin struggled to keep a straight face. The third dart managed to hit the board before drooping and clanking to the floor. He burst out, a guffaw so great I wished the floor would swallow me whole. I shrugged my shoulders and recommended that I move from active duty to the cheering section.

There is an awesome bar that has live jazz called Fat Cat. In addition to music, it is also full of games – checker boards, pool tables, ping pong tables. Sam was dying to go there for the tunes, at least this is what he told me. But once there, he really wanted to play ping pong. I tried to get out of it but before I knew it I had a paddle in my hand. I missed the ball nearly every time, I would have had more luck if I’d just closed my eyes. When I did manage it hit the ball, it went zipping off through the air to strike someone or interrupt another game. I spent most of the night crawling under pool tables and tripping over feet to find the little devil. Needless to say, Sam won and the management forbid me to play. Ever again. In fact, they may or may not have snapped my picture and kept it on file for the doorman so that he could bar my future entrance. It was that bad.

Ed wanted to go bowling. I knew I was in big trouble but we were at a mall that had a bowling alley and it was raining and the movie we had wanted to see was sold out. “Drats”, I said, “I don’t have socks”. I pointed to my sandaled feet. “They sell socks,” he replied with a grin. Ed was good, I was not. After many gutter balls, Ed kindly said, “it’s all about the release” and then showed me in slow motion what to do. I stood, waited for the perfect moment then swung my ball back as I moved forward. It was going to be great, I could feel it! I swung the ball out, and, and, well I got caught up in the moment and I forgot to release. With a thump, my whole body landed in the lane, my ball still on my hand. Of course, Ed rushed to my side as he tried not to laugh. He kind of gave himself away though when he mentioned his desire to have caught the whole thing on video. I didn’t have the heart to admit that once upon a time I’d taken a bowling class, in college, for credit!

There are those who are naturals and those who can become better with time. I am neither of these and unless my dates are needing some comic release, it is probably best I remain a spectator. Although, I’m always up for Clue!

Keep Your Clothes On

I’ve noticed something strange going on in online dating. People seem to have become less inhibited. I’m not sure if it’s because people feel more comfortable in the comfort of their own home, and this makes them believe it’s all right to share more, or if it has something to do with the cloak of anonymity that going online offers, but I think people are oversharing. And I’m not talking about too much information (although this happens too)—I’m talking about too much skin! Sure, tawdry websites exist where skin is accepted, or even expected. But even mainstream online dating websites are full of scintillating pics. What’s more, there seems to be no holding back, no intrigue, no building up to sharing these kinds of photos. They seem to be expected automatically, quid pro quo.

Case in point, not too long ago I put up a very cute, light-hearted entry on a dating website that mentioned the fact that I have a dog, among other things. I received a nice, short note from a cute fellow dog-owner, along with a photo of him and his dog. Awwww, I thought, how sweet. He came across as likeable and someone worth continuing to correspond with. I replied with a brief note.

When I heard back from him, he included about fifteen pictures (this is never a good sign – there is a direct correlation between the number of photos sent and the size of the sender’s ego). The first picture I opened was minus his four-legged friend . . . and minus most of his clothes as well! He stood, back to the camera, striking a body builder pose in slinky black underwear. Eeewww! “What in the hell is wrong with him?” I wondered as I deleted his e-mail. I’m sorry, but on what planet is this all right? I do not even know this guy!

Along with guys who show too much skin, I’ve met guys online who want to see too much skin. I have a girl-next-door picture I routinely use for online dating. It’s a shot of my face and captures me smiling, my hair smooth (for once!) and not in disarray. Maybe my earrings are bit on the big side, reminiscent of Madonna in the eighties, but overall, it’s not a bad picture.

I cannot count the number of times that I have received e-mails from men asking for a body shot in response to this photo. It seems to me that these men want to receive full body pictures so they can see some skin (preferably with cleavage) and to ensure that I have a “healthy height to weight ratio” (yes, these were the exact words used in one exchange). I always want to shout back in all caps: “Excuse me, VAIN MUCH?!” Call me crazy but I would like to, ahem, get to know someone before doing even a quarter-Monty. And as for sending a full body shot to people, the day that men wear high heels on a regular basis is the day that I will even start considering this. I have come to the realization that I wouldn’t want to date any of these egomaniacs anyway and I delete, delete, delete.

My friends keep reminding me that men are visual creatures. I get this, I really do. And honestly, there is nothing wrong with showing some skin after things have progressed a bit beyond the initial e-mail exchange. A past boyfriend of mine sent me some very nice shots once, reminiscent of Marky Mark in his Calvin Klein modeling days— but this was after we’d been dating for some time. And even then, my first reaction was to laugh (sorry, near-naked men sometimes have this effect). My second reaction was to think he should perhaps try to become a Calvin Klein model, seriously (loooooong sigh).

But when I’m getting to know someone, meeting and greeting them for the first time, talking about where they grew up and whether they have brothers and sisters – I don’t even want to be imagining what they look like in their underwear. So, please men, keep your clothes on (at least for a while!).