So you wanna climb the mountain, huh?

*******For those of you just joining Cheeky Reality, you need to catch up. In fact, before you go any further, if you haven’t done so already, you need to read the first installment of this three part “blog series” so that you won’t be lost. In the first part, we address the Friend Zone and how the different levels of the FZ directly relate to the seven circles of Hell in Dante Alighieri’s Divine Comedy. You can read all about that here.*******************

Welcome to Friends with Benefits! Purgatory personified.

“The soul, which is created quick to love,
responds to everything that pleases, just
as soon as beauty wakens it to act.
Your apprehension draws an image
from a real object and expands upon
that object until soul has turned toward it;
and if, so turned, the soul tends steadfastly,
then that propensity is love – it’s nature
that joins the soul in you, anew, through beauty.
Then, just as flames ascend because the form
of fire was fashioned to fly upward, toward
the stuff of its own sphere, where it lasts longest,
so does the soul, when seized, move into longing,
a motion of the spirit, never resting
till the beloved thing has made it joyous.
Now you can plainly see how deeply hidden
truth is from scrutinists who would insist
that every love is, in itself, praiseworthy;
and they are led to error by the matter
of love, because it may seem – always – good;
but not each seal is fine, although the wax is.” (Purg. XVIII, 19-39)

PurgatorioItalian for “Purgatory”.

Purgatory literally means a condition or place of temporary punishment.


After surviving the seven circles of Hell (the Friend Zone [FZ]), our hero, Dante (you), has emerged onto the banks of a secluded island in the Southern Hemisphere of the world. Standing before him is a gargantuan mountain, Mount Purgatory (henceforth will be FwB [Friends with Benefits]), complete with seven different terraces of mindf**k.

As if the FZ wasn’t bad enough, here are new obstacles to overcome!

From the shores of Ante-Purgatory all the way up to Earthly Paradise (Heaven, and that will be the next and final installment in this), there are walls and potholes and minefields and bombs and grenades and legitimate dirty shit to navigate around,

I really hope you brought a helmet because it’s not only seven levels of Purgatory, it’s the seven different types of Friends with Benefits relationships.

It’s messy, it’s chaotic, it’s littered with wrong turns and broken hearts. It’s eager, it’s anticipative, it’s buoyant with hopes and dreams of something more. But above all, it’s a hassle. A hands-down, you-don’t-want-none-of-this-crazy type of raging headache.

It drives the best of us insane.

It deprives you of your emotional wants while fulfilling your carnal desires. A real one-two-punch straight to your blood-pusher (your heart).

To be fair, it’s not really that bad, but it does have definite potential to become a serious issue in your life if you don’t know what the boundaries are.

Like everything in life, there must be rules. Without limits, your heart pushes past any realistic expectations your mind can’t deal with. And that’s how you get clingers.

Clingers, most often are women unfortunately, but for anyone, tripping into Friends with Benefits territory can quickly become a nightmare. The constant analyzing of every single, little, teeny, tiny action or word can lead you to going insane. Like, full-on, bat-shit crazy insane. If you’re lucky, however, you can deal with it like a big girl and just cry over it with a box of wine and a copy of 50 Shades of Grey.

Of course, if you find yourself lost with no idea on what kind of relationship your FwB is, I’m here to help! From here on out you can refer to me as your wingman, your bestie, your ride or die go to for anything concerning the Friend Zone or Friends with Benefits, guide. You may call me Virgil.

First Terrace (The Proud):

We’re going to start off the first level of suck with a positive note.

Successful Transitioning or Transitioning In.

Put simply, a successful transition from the FZ to FwB is any two friends that started out as buddies and knowingly and willingly transitioned into a couple. Whether or not that couple lasts is really null and void, it’s a proud accomplishment that it happened. You went in for the kill and were rewarded with an endless supply of booty, and the best part is, it’s not booty by yourself (your hands will thank you later).

On this terrace of Purgatory, you are free to celebrate, victory dance, John Cusack it up with a boombox on the front lawn underneath a window, anything. You can shout it out to the world that you got the girl (or the guy)!

“Here’s the deal sparky, ya wanna court the little lady, ya gotta be a straight shooter. Got it?”


Second Terrace (The Envious):

Just like Transitioning In happens, Transitioning Out does as well.

This type of relationship is particularly tricky because of the circumstances it normally happens under. Transitioning Out (TOing, not to be confused with TEBOWing) is when a couple breaks up but continue to sleep together, thus the envious nature of this relationship.

Picture this:

You dated this girl forrrrr, let’s say, seven months. Seven is a good number. Long enough to invoke some strong, solid emotions about her, but not quite stretched out enough to warrant hanging on forever.

You picturing it?


You dated for seven glorious months. You break up for reasons not important. Next thing you know, you’re not getting anymore action. You’ve been forced to resort back to Jergen’s and tissues while you gorge yourself on Mountain Dew and Hot Pockets playing GTA V. You haven’t made it back onto the bar scene to pick up a random chick, much less even showered. Dude, you STINK!

You see the problem here?

With no other options and a serious case of back-up happening down south, you call up your ex, and she may (or may not) have enjoyed your physical relationship enough to continue it without the exclusiveness of being a couple.


Kind of.

What you haven’t realized is that TOing is going to be your mega-boss. Your metaphorical Ganondorf in Ocarina of Time while having three hearts left and no more fairies.

To put it bluntly-you’re screwed.

You now have to watch the girl you just evicted from your arm, flirt and fall in “Facebook love” with someone else. And because you’re still tapping that, you know exactly what you’re potentially sharing with someone else (I’ll give you a hint, it’s not your car). This is where you either stop sleeping with her altogether (not recommended if you want a raging case of Turquoise Turtles), or you get down on your knees, kiss her feet, and beg her to forgive you for being so dumb as to let her go. Because trust me when I say that the ONLY reason you’re still getting a piece of her is because she’s secretly hoping you wake up from your “it’s not you, it’s me” phase.

Time’s a wastin’ so you better figure out which route you want to go quick, fast, and in a hurry.

Third Terrace (The Wrathful)

This terrace is the WORST. This is the level where hopes and dreams get shattered and salty tears flow freely over six too many shots of Jim Beam.

If you’re sitting on this terrace of Purgatory, I’m sorry.

You have suffered the dreaded Failed Transition and the aftermath is ugly.

But just to be clear, Failed Transitioning isn’t necessarily failing to leave the FZ. This is all encompassing, to include, you and your friend trying to date but failing harder than taking a super-cute selfie in front of an open toilet with a turd floating in it.

You failed, damnit! And you’re angry about it, possibly even downright wrathful!

You’re mad at yourself for wearing a mock-turtleneck on your first official date and telling her you love her with tears in your eyes after you hooked up for the first time.

Honestly, I want to feel sorry for you, but I can’t, I just…..can’t.

Number one, if you have a mock-turtleneck in your closet, get rid of it. Those things were made exclusively for Zach Galifiankis in “Dinner for Schmucks” and it was hard for even HIM to pull off. Burn it. Now.

Number two, if you cry, EVER, after a really powerful Marvin Gaye encounter, please put yourself back in the FZ, because it is guaranteed that’s where you’re going. If you have to ask why, excuse yourself from this blog and consult Google. I don’t have the time or the patience to teach you how to not be a wuss.

Fourth Terrace (The Slothful):

Slothful is, to me, the best level of Purgatory to hang out on if you had to really pick one. It’s the slow and steady if-you’re-ready level. It’s the Unintentional Transition. The kind of thing that sneaks up on  you and BAM! Exclusive coupleness has leaped on your back like a friggin’ spider monkey!

What’s that, you say? You don’t know how it can surprise you like this?

Allow me to clarify.

You and your pal are taking things slow, enjoying each other’s company, a little casual dating here and there, and just genuinely having a good time. You’re going out to dinner, watching movies, even sneaking in a bit of cuddle action after the ‘boom-boom’, when suddenly….you look at your friend and your grey skies are no longer grey. The clouds have parted and you see that the person you’ve wanted, no, NEEDED to be with has been right in front of you the whole time. But in order for the “unintentional” part of this to work, both parties need to come to this realization at roughly the same time. That leads to sending cute messages to each other, telling each other “I miss you” or “I can’t wait to see you”. The “unintentional” is just that-unintentional-because you started out your FwB situation with no expectations for more involved romance. It just kinda happened.  You solidly believed that there were no serious feelings involved, and there’s a good chance that in the beginning, there wasn’t. Not anymore…..mwuhahahaha!


In my experience, these are the best kinds. You get to learn your friend on a very in-depth level, and more than likely, they are one of your closest friends. Unintentional Transitioning has the highest success rate of lasting couples out of every FwB situation. That’s a fact. Look it up.

Fifth Terrace (The Covetous):

Ahhh, we have reached the very edge of FwB transitioning and situations with known friends. True Friends.

To be completely honest, this terrace is kind of boring. This is your straight-up, nothing-but friendship level.

You and your sidekick have established a strictly platonic relationship with no chance, whatsoever, for it to develop into more. That means no flirting with each other, no nervousness over what you wear when you hang out, no jealousy over who they’re talking to, nothin’.

In fact, this is where the covetous part of the relationship may come into play. You guys are such great friends that you are covetous of each other’s time. Odds are you’re ruining their chances with someone because you’re so close.

No guy wants to date a girl who’s best friend is also a guy that hangs out with her 25/7. And yes, I meant 25 hours of the day. You guys watch scary movie marathons and eat so much popcorn together, the rest of the world inserted an extra hour into every day for you to enjoy your time together.

Occasionally, this type of relationship does turn into something more, due to someone’s epiphany about how cute their bestie is, but that’s the exception, not the rule.

Just play it safe on this one. If neither one of you have any deeper feelings, don’t question the nature of this relationship, because it’s only going to get difficult for one of you as you start your descent through the Inferno.

Sixth Terrace (The Gluttonous):

You ever have a drunk one-night stand with a kinda sorta friend that you kinda sorta know?

Don’t lie, everyone has. Even if it was a normal one-night stand with a stranger that later turned into an occasional “Hey, sup?” it counts.

Welcome to Network Opportunism, home of the greedy and gluttonousMost of the time, these kinds of hook-ups are often fueled by RedBull and Vodka (at least for me anyways) and don’t come with any kind of emotional attachment to that person. The gluttonous part comes in where this is the only kind of hook-up you’re experiencing.

You are more than likely too selfish or too much of a player to genuinely care about other people, so you do what works. One-night stand after one-night stand. How many women are you going to force to do the ‘walk of shame’?

Seriously, no one wants to be alone all the time, and at some point you need to move out your college frat-boy personality and into a more responsible adult frat-boy one. (Face it, once a frat boy, always a frat boy, Sorry.)

I mean, I’m not knocking you. Whatever works, but at some point, you’re going to get tired of buying condoms and want someone there that you explicitly trust to not give you the full-body karate, and you’re not going to find it at the bottom of a bottle in mini-skirts and stripper heels.

Seventh Terrace (The Lustful):

Our seventh and final level of Purgatory is all about the benefits without the friends.

Straight-up NSA lust.

Throughout my life, I have met multitudes upon multitudes of men that strive to find the infamous F**k Buddy (FB). The woman they seek is someone who will come over at 2 AM to ‘do the do’ and leave without even an attempt at cuddling, and believe me, it’s hard to find. Occasionally you’ll find a woman that wants a situation like that, but it’s certainly a lot easier for her to find a man that doesn’t want a sandwich afterwards, than it is for him to find a woman that won’t invade his bathroom with tampons and pink sponges after two nights of playing ‘peek-a-boo’.

These FBs may be friends that have no interest other than ‘slam-bamming’, but most often it’s an acquaintance you don’t see or talk to all that often in order to keep the emotions down.

Here’s a sign on if you happen to be or know one of those people:

If she never wears perfume, doesn’t take the time to fix her hair or makeup, or comes over right after the gym, she is a FB. She has no interest in what you think about her, and puts forth minimal effort in looking presentable.

If he doesn’t shave his 5 o’clock shadow, doesn’t take his clothes off during the nasty, or doesn’t care whether or not you have a significant other, he is a FB. He has no interest in what you think about him and will probably never care.

After ascending these seven levels or Mount Purgatory, whether through some form of transitioning or other approaches, our lovable Dante has now reached the summit and can see the Earthly Paradise, and so can you.

But if this article hasn’t cleared up enough for you and you still have questions on what level you and your FwB are on, you can refer to these easy to follow charts.



And don’t forget that we still have one more part in this Divine Comedy of the Friend Zone, Friends with Benefits, and the techniques used to exit these two things, so I hope you will check back with me to finish it out.

Thanks for reading! Feel free to comment and share!

******Don’t forget to like Cheeky Reality on Facebook to stay up to date on the newest blogs! If you have any ideas on what you want to see next, please drop a comment or a message!********


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