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The Perils And Pleasures Of Dating A Player


He sure knows how to treat a woman—but monogamy isn’t his strong suit. Our writer asks, is he worth it?

By Natalie Krinsky

he phone call came late on a Sunday afternoon. My boyfriend Ben and I were sitting amidst the remnants of four bags of Doritos watching football. On the line was his best friend Oliver—player extraordinaire and the most delicious Australian I’d ever encountered. While my schlub and I lounged, Oliver had taken his newest acquisition, Robin, shopping at Barney’s for whatever tickled her fancy. My fancy, on the other hand, was ticked off. I wondered, what I was doing with a guy like Ben when I could be gallivanting with a specimen like Oliver? The truth is that though dating a player has its major perks (for instance, he knows what to do and say to leave you weak in the knees), it certainly comes at a price. Let me explain:

Pleasure #1: A player will always make you feel like an incredibly hot girl in a hip-hop video. A close friend of mine, Breanne, 33, began dating a very well-known, well-connected and (apparently) well-hung Hollywood producer. She ate well, traveled in style and never waited in a single line, anywhere. Her vacations consisted of last-minute jaunts to St. Bart’s, romantic voyages to Paris and lazy weekends on Martha’s Vineyard,
I wanted to fall asleep in his arms, knowing he wouldn’t bail before brunch.
during which she always looked the part in carefully selected wardrobes (jewelry included) to match each destination. Soon enough, the producer’s birthday rolled around. Which leads me to the first con of dating a player…

Peril #1: There is never only one incredibly hot girl in a hip-hop video. This guy’s birthday party was held at a chic New York nightspot filled with scantily-clad dancers and the who’s-who of the entertainment industry—not to mention more beautiful women than the Sports Illustrated swimsuit issue. Breanne wondered just how her devoted boyfriend became acquainted with so many genetic treasures. Her curiosity only deepened as she watched him flutter between three or four other beauties, engaged in what certainly didn’t seem like innocent birthday greetings.

Breanne realized that her boyfriend was, well, not all hers. She may be the favorite, but she certainly wasn’t his one and only. "I guess I’m ‘first wifey’ or something," she said with a wry smile. She recovered from that day, and soon, Breanne began looking for a new boyfriend—one with fewer girlfriends.

Pleasure #2: A player has all the right moves… A man whose relationships typically last a couple of weeks or months knows a thing or two about rising to the occasion in the bedroom. Take Sebastian, a player I briefly encountered in college. He was the apple of every girl’s eye, and for a couple months, I had him all to myself. We joked and flirted over drinks and when we went back to his place together, his bedroom was perfectly lit; he brushed the hair out of my face and whispered the sweetest sweet nothings in my ear between soft kisses. I was blissful for weeks.

Peril #2: …But meaning behind his moves rarely exists. Sure, players have the mechanics of sex down cold. And cold is an apt word, because when it comes to real soul-to-soul, heart-filling, eyes-locking sex, they fall short. A genuine connection
Alicia knew better than to make him endure the dreaded “where is this going” conversation.
demands a certain intimacy that a player never manages, or wants, to accomplish, which is why I couldn’t continue indulging in Sebastian and his amazing bedroom moves. I wanted to fall asleep in his arms, knowing he wouldn’t bail before brunch.

Pleasure #3: The best part of dating the player is the challenge. Another close friend, Alicia, 27, began dating Barry, a man she knew was a player—a finance-guy player, to be exact. Imagine that your job was to find the stock or bond that’d be the best return on your investment. How, then, could he not always be looking for the newer, better woman? Alicia knew all this, and told herself that she would be the one to conquer uncharted player territory and make Barry stay for a while. She wouldn’t ask too many questions, nor would she make him endure the dreaded "where is this going" conversation. Alicia relished the prospect of being the first girl to win Barry’s heart. She even enjoyed that she had her own independence in the relationship. Barry never minded when she canceled plans because of work or a girlfriend crisis. That is, until she realized that Barry, and players in general, always have a back-up plan. And a back-up plan for their back-up plans.

Peril #3: Odds are, you will fail in your player-taming. One evening, walking home from work, Alicia passed a trendy New York restaurant, and there, in the window was Barry dining with one very attractive woman. Hoping that they hadn’t seen her, and remembering her vow to be "different than the other girls," Alicia seethed in silence. By the time a few weeks went by, insecurity was with her 24/7. She couldn’t stop second-guessing herself, wondering where
“Baby, the commitment thing, I just don’t do that,” were his parting words.
Barry was at every moment of the day, and why she wasn’t wonderful enough to keep him from playing the field. Eventually Barry broke off the relationship with a simple, "Baby, the commitment thing, I just don’t do that," and found a Brazilian model or two to occupy his time.

So, at the end of the day, are players worth the ride? I asked my girlfriends, and, despite some hilarious yet horribly painful stories, they all reluctantly agreed that a player could make you feel like the most exciting and desirable woman in the world, if only for a moment. For that reason, we should all date a player once. Like going on safari, it’s an incredible adventure when you’re there, but once you’re home on more secure terrain, you’re probably very, very grateful.


Natalie Krinsky weeded through many a player while writing the Yale Daily News column, “Sex and the (Elm) City.” She's the author of Chloe Does Yale.
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