In my mind, every relationship pretty much starts off as a fling. We live in a world now where courtship, as they once called it, kind of doesn’t really exist. We meet people through friends or at bars or shows, and we drunkenly hook up. If the sex is decent and that person doesn’t totally repulse us when the sun rises and we sober up, we might think about giving them a text again some day. This is one version of the way we shack up.

The other involves the internet. Forget about the mundane regularity of dating sites (meeting someone online is no longer just reserved for so-called pathetic nerds and widows, but for all of us), social media and online profiles allow us to completely scope out, stalk and judge potential suitors from the comfort of our smartphones.

We can communicate in the online world for months without ever meeting IRL -- that’s web talk for “In Real Life” -- and get to know that person through our carefully calculated online personalities and Facebook profiles. So, when we eventually do meet up IRL, we feel as though we know one another and intimacy occurs quickly.

Today, courting, dating and waiting for that first kiss are pretty much an old-school joke. We have careers to focus on, friends to hang out with and our own satisfaction comes first. Flings just work in our fast-paced world.

But what happens when your hookup partner starts to seem like an attractive option for a real relationship? How do you venture into that new territory? How do you turn a fling into the real thing?
Read The Signs And Ask The Questions
Let’s assume that you and your fling have been hooking up for a seemingly significant amount of time. This is why you’re interested in taking it to the next level. Before vocalizing any interest in turning your casual hookups into a full-blown relationship, I suggest perception. Look at the nature of your current situation.

Do you only text one another for late-night sex? Do you hook up when you are sober or just drunk? Do you have sleepovers, or do you leave after the sex is over? Have you ever shared a meal, hung out and actually had a decent conversation?

Who does the initiating of your meet-ups? Is it generally even? Do you know one another’s friends? Is your sexual relationship a secret or is it known by your friendship circles? Do you feel respected by him/her on a human level? Could you imagine being friends with this person?

From my experience (and, trust me, I have a lot of experience) the most loving, lasting and healthy relationships are the ones where you feel as though you are dating your best friend -- someone you trust indefinitely and can grow with.




Some may argue that it’s difficult to maintain a relationship, and while that belief certainly has merit, let’s not discount the inherent challenge involved in keeping friends with benefits. Walking the fine line of blissful, casual enjoyment -- with a committed relationship on one side and the loss of your bed buddy on the other -- is a risky balancing act, and you must control the weight distribution.

Every Player’s little black book should be filled with friends with benefits, who are female friends offering those benefits with passion and skill. Now, bear in mind that we’re referring to those girls who are more than sexual acquaintances, in that they’re above a drunken 3:00 a.m. booty call, but not adverse to a simple roll in the silk-laden hay. In fact, we should probably differentiate between acquaintances, friends and the topic of this article: the Player does indeed have many friends (he’s a likable guy, after all), and as evidenced by lovely individuals like Lauren and others in recent “A Day in the Life” episodes, he also has female friends. There is, however, a significant difference between regular ol’ friends and friends with benefits. Sex is involved, my fellow Casanovas, and that changes everything.

Perhaps you believe a mini-instruction manual on this subject isn’t necessary, just because the very idea of having friends with benefits appears to be devoid of problems. On the surface, having a friend with excellent fringe benefits may appear to be the simplest, easiest, most straightforward relationship one can have. However, once you experience the process and realize just how many obstacles lie in your path, you’ll quickly understand that no relationship is straightforward. In fact, when it comes to the fairer sex, nothing is.
Never Be A Shoulder To Cry On
It’s the single biggest mistake a Player can make when attempting to maintain a friendly relationship with a willing and sexually able female. The two of you will chat now and then, laughing and having a good time on the weekends whenever you bump into each other. There’s no schedule (you’re not dating), so there’s no commitment and no time to get involved in emotional discussions. Once you become friends, however, there may come a time when her ass-of-a-boyfriend tosses her away like a used tissue, and immediately afterward, she comes to you with… well, with a box of tissues. She calls you up in the middle of the night, crying her eyes out and failing to convey the tragedy due to unintelligible words sprinkled amidst the sobbing. You make a classic error and say, “I’ll be right there,” which lands you on her couch at four in the morning saying things like, “He doesn't deserve you,” and, “Wow, he sounds like an idiot.” Verbal mollifying leads to physical soothing, soothing leads to caressing, caressing leads to wandering hands, and finally, wandering hands leads to breakfast together. Yeah, oops.

Now, you may be able to extricate yourself from the freshly developing relationship by playing the “I don’t want to take advantage of you when you’re on the rebound” card, but it’s still a mess. To avoid the mess, avoid the tears. You’re a friend, but you’re not a childhood friend and you’re certainly not her boyfriend. Be polite and even helpful, but stay strong and keep your shoulder to yourself -- that’s not the job of friends with benefits.


Don’t Worry Too Much About Appearance
You may recall what Billy Crystal said to Meg Ryan in When Harry Met Sally, one of Rob Reiner’s better films: “You can’t be friends with somebody you find attractive.” Neither of you can help it if you’re one of the pretty people, but there’s no need to reinforce that fact. You needn’t halt all hygiene exercises, but when you’re going to meet her for a quick drink, leave your nice jacket at home and don’t bother with the expensive cologne. Maybe you didn’t get a chance to shave that morning and you let it slide for a few more hours. In other words, just dress as if you were headed out with the guys. Simple, right? You’re not dressed like a bum on the sidewalk, but at the same time, it’s clear you’re not going out of your way to dress up for her: Downplay your irresistibility and the message is subtle yet clear.

Now, you mustn’t go overboard in this scenario -- not only do you have a reputation to uphold, but you also don’t wish to turn her away. After all, her skills behind closed doors shouldn’t be ignored (only a fool would willingly pass up such amazing encounters). However, you have to remember that you’re not dating this woman, and you can make that abundantly clear with two things: casual behavior and casual dress.
Pay Attention To Your Post-Sex Behavior
Finally, there is always that awkward moment immediately following the hot, sweaty cardiovascular workout, the moment that is crucial to the future of your newfound “friend with benefits” relationship. Your very first impulse is a common and reasonable one, but if you give in and forget your situation, the relationship mode is inevitable. The default impulse prompts the man to make plans with her for next weekend, and it requires a variety of sweet-nothings and a smattering of “you were amazing’s” and such. Now, while you certainly don’t wish to de-emphasize the greatness of the encounter (no need to hurt her feelings), you also can’t adopt boyfriend behavior. If you act like one, you will soon be one. You had a good time, obviously, but you’re vague about your weekly schedule, breakfast in bed is absolutely out of the question and it’s probably best if you keep things open-ended. This is crucial when it comes to friends with benefits. You’ll give her a call the next time you’re free, and that may or may not be next weekend. Light and breezy is the name of the game; in fact, it’s the very definition of interaction between friends with benefits.

Whatever you do, don’t ignore the standard rules that apply to all men after sleeping with a woman. If you need me to list them out for you, you aren’t in any position to handle this article in the first place.
Be That “Special” Friend
There are friends, and then there are friends with benefits. If you make the mistake of classifying such an individual as a straight “friend” or, God forbid, a girlfriend, then you’ve missed your target… and your chance. Believe it or not, most men don’t have the patience or subtlety to maintain a solid friendly relationship with a woman that also includes sex. Either they overstep their bounds right away and slide into full-on commitment, or they spend an ill-advised hour consoling their friend, ramping up the intimacy to Olympic levels. After that, she can only be a close friend or a girlfriend, and the benefits suddenly have all sorts of caveats and conditions. In order to have your cake and eat it too, you need to blend the word “acquaintance” with the term “bed buddy,” which results in a hybrid relationship that yields big results. Friends with benefits are like driving a Ferrari that gets 45 miles to the gallon!