I've been sleeping with a close friend on and off for three years. He had a girlfriend during an "off" period, and I've slept with other guys, but I can't invest in anyone else because

I've been sleeping with a close friend on and off for three years. He had a girlfriend during an “off” period, and I've slept with other guys, but I can't invest in anyone else because he's always on my mind.

We've talked about the fact that there's a vibe between us, but neither of us see it turning into a relationship. Me, because I've always been single and don't want to complicate my life by entering into that world just yet. Him, because he thinks we've been friends for so long that we wouldn't work as a couple.

Despite this, I still have really strong feelings for him and I don't know how I'm ever going to like anyone else.

We are both part of the same social group and see each other at parties etc. on the regular, so it's hard to move on when he's ALWAYS THERE.

He's also very closed so it's hard to know how he really feels about me. I want a straight answer so I know whether he feels as strongly about me as I do him, or whether he's just in it for the sex.

Either way, I don't know how our friendship could last, because if he hurts me by saying he's not into me, then I'll always feel resentful towards him, but if he says he IS into me, I'm not going to be able to move on.

Hello Fren,

This is a shitty limbo to feel stuck in and I am truly very sorry.

You claim you do not want “a relationship” because you’ve “always been single,” and you “don’t want to complicate your life.” The very premise, then, of your question as you’d have me believe it is: 

“There’s a guy I do not want to be with. But I desperately need to know if he wants to be with me otherwise I can’t move on.”  

Sorry, and so much love to you, but this makes absolutely no sense. Go back to your letter and count how many times you mention your strong feelings for him. The answer: very many!

So, FYI, here’s what your letter actually says:

You have been in a friendship-with-benefitship for three years; you have feelings for him, but his behavior, which feels hard to read, does not necessarily indicate that he shares those feelings; you do not want to upset the applecart and scare him off for good, so you are just pretending everything is fine and secretly wishing for something else, meanwhile growing resentful that he’s not giving it to you, and you do not know what to do.

Let’s start there.

The big headline: you are already in a relationship, and your life is already “complicated.”

But what are the terms of this relationship, how did y’all get here, and most importantly, how is this relationship making you feel?

The even bigger headline: you are unable to see all this because you have been semantically and conceptually scrambled.

Is this his fault? Yes.

Is this your fault? Yes.

Is this patriarchy’s fault? Yes.

The diagnosis: you are caught in The Chill Trap. What is The Chill Trap, you ask? Great Q!!!! Let’s unravel all of this by defining our applicable terms:



A relationship built on mutual respect and good boundaries. Can be platonic or “very special” *wink* *wink* *wink*

Backburner Ass Bitch:

A consistent partner in one’s “"hotation" (S/o Issa Rae). Can be used affectionately or not.   

Ethical Casual Sex:

Sex, brought to you by: Sex!  

A friendship that features some sex that is built upon a mutual agreement that there are no immediate plans for anything beyond “just” sex. Please note: keeping casual sex “casual” does not guarantee that its practitioners will a.)Never have a feeling, or b.)Never get hurt; to practice casual sex ethically means that both parties are comfortable communicating with regards to article a and article b. Consensual and affectionate Backburner-Ass-Bitch-ing.


Sex, brought to you by: Feelings!

Relationships are whatever the fuck you want them to be. If you find someone you like fucking who you also like hanging out with, who also has some special feelings about you, voila! Relationship! The institution doesn’t require l-i-t-e-r-a-l-l-y anything else. No pressure to get into one, but being “against” relationships doesn’t mean anything. Human beings are social animals. We were made to relate to one another. The culturally-imagined heteronormative monogamous construction of relationships as atomic units of Capitalist participation need not apply to you; (*hits blunt*) there are no rules if you choose not to follow them.


Any and all behavior on the part of a womyn or femme that does not make a toxic hetmale uncomfortable.

The Chill Girl:

Identity, brought to you by: Hetmale Fuccboi Expectations!

The Chill Girl is a toxic, heteropatriarchal trope that is all-too-often often mirrored back by womyn who have learned that the affectation of Chill is the path of least resistance to achieve a minimal level of acceptance and positive regard. Her only quality is her Chillness. She doesn’t exist unless he is literally inside of her. She cheerfully demands nothing of him, and happily munches away at the sexual and emotional scraps he tosses her from his proverbial plate. Yum! She knows better than to act crazy. It’s not like they’re in a relationship or anything. The Chill Girl shares a lot of The Cool Girl’s DNA, with a few key differences, namely, The Chill Girl is nobody’s girlfriend. Because relationships are not Chill. If she speaks up for herself or challenges the toxic hetmale monolith in literally any way, her identity as the fuckable Chill Girl becomes void and she suddenly transforms (*gets wet* *becomes gremlin*) into The Psycho Bitch (see: The Psycho Bitch). Once she has become The Psycho Bitch, all her dick privileges are revoked. You Chill Girl yourself when you mistake some of the tenets of Ethical Casual Sex for a fixed identity; you Chill Girl yourself when you mistake fuccboi expectations for a fixed identity, for an identity you must inhabit.    

The Psycho Bitch:

Self- Respecting Femininity, brought to you by: Toxic Masculinity!

The Psycho Bitch is a projection designed to protect fragile toxic male egos. The #1 rule of The Psycho Bitch is that any and all males have the power to transform you into The Psycho Bitch at their convenience, or as a passing fancy. Psycho Bitch behavior is evident in any/ all of the following actions when performed by a womyn: 1.)Any action; 2.)Challenging a toxic male either publicly or privately to examine his behavior 3.)Expressing the expectation that she is treated like a fucking human within a casual sex scenario. The Psycho Bitch is only real if you buy into her. Clap your hands and believe! (Or like… don’t, you know?)

Self- Respect:

Your needs, brought to you by: You!

Actions and words that express one’s own needs and boundaries motivated by self-confidence.

The Chill Trap:

Casual sex, brought to you by: Internalized Heteropatriarchy, with special funding from Bad Boundaries. Made Possible By Fuccbois Like You.

A scenario in which ethical casual sex (see: Ethical Casual Sex) is forfeited in favor of a friends-with-benefits arrangement in which one or both parties sublimates any and all human feelings, self- respect, and expectations of being treated like a fucking human in order to promote a false sense that everything is Chill (see: Chill). Very often, the person who is performing Chill to their own detriment is a womyn or femme, and the person who dictates the terms of the Chill is a het/male, guided--consciously or unconsciously-- by toxic masculine tropes. This is done in a misguided effort to do a “good job” at casual sex-ing, to protect one’s own vulnerability, and to avoid rejection and social consequences; this is done in an effort to become and to stay Chill; this is done in an effort to avoid being seen as The Psycho Bitch (see: The Psycho Bitch).


Now that we’ve defined our terminology, it sounds like you are unhappy, but have gotten Chill Trapped into believing that you do not want the conditions of this relationship to improve. Because you’ve come to believe that you’re not in a relationship, because you’ve come to believe that relationships aren’t “Chill.”

It seems that the two of you entered into the agreement that your friendship-with-benefitship [sic: relationship] was to be built on the shaky tenets of Chill. This agreement has never been spoken of again, let alone re-evaluated or amended in three long years.

If finding out that he is “just in it for the sex” would devastate you, then you must immediately take the actions necessary to let him know that you are not “just in it for the sex.”  

I am here to tell you, there is nothing wrong with asking for what you want. Get comfortable with that.

There is nothing wrong with wanting someone that you have such strong feelings for to have the same feelings towards you. There is nothing wrong with wanting affection and approval reciprocated on your terms.

The fact that you feel the need to preface your feelings by immediately minimizing their importance is born out of Chill Trap thinking that tells you that you are not allowed to ask for anything.

Ethical Casual Sex feels different from what you are describing, which is to say, it doesn’t feel emotionally torturous and doesn’t put you in the position where you feel you have to hide your wants and needs-- Ethical Casual Sex is built on good boundaries and good communication; it is fulfilling within a comfortably narrow scope. This is not.

To feign Chillness as a permanent facet of your identity is dishonest and it is not serving you. As I’ve said, if you don’t voice what you actually want, you will not get it. And if you don’t voice what you actually want, you are wasting your time being outraged.

It’s very possible that your friend has followed your cues up to this point. It’s possible that, in an effort to appear Chill, you have never indicated that you have strong feelings for him, and that he is thusly in the same position you are in: trapped in the Chill.  

It is also very probable that his behavior has indicated to you that he does not want a relationship with you beyond a friendship-with-benefitship, and that you are energetically molding yourself around his projection and expectation that you are, and will continue to be A Chill Girl.

What I’ll point to-- this may be hard to hear, and I am sorry, because I know it sucks-- is that he has had a girlfriend during one of y’all’s “off-again” times. It sounds like he is a person who knows what he wants, and is able to make it happen for himself-- becoming someone’s boyfriend typically requires pretty emphatic intent and consent. It sounds to me like you might be filling in the massive gaps in communication with your own feelings.

What I’m saying is: if you hear hooves, it’s probably not a zebra.

Maybe I am wrong, but the rules of male entitlement suggest that he is currently getting exactly what he wants.

Let’s talk culpability. Because where there is The Chill Trap, there is shame, where there is shame, there is anger, and where there is anger, there’s a useless but urgent vacuum demanding to be filled with blame, and it just might be helpful to sort everything out.

His fault: being emotionally closed; not communicating his intentions or his needs; assuming that everything that’s gone on in the course of your friendship-with-benefitship has been exactly what you’ve expected, wanted, and needed without double-checking with you; potentially intimating that this “vibe” between you means more than it actually means in an effort to keep you as his Backburner Ass Bitch while obfuscating his actual intentions; lazily, and either consciously or unconsciously relying on his male privilege to keep you on The Backburner by relying on a falsely constructed dichotomy of The Chill Girl vs.The Psycho Bitch, rather than following the rules of Ethical Casual Sex.

Your fault: being dishonest about your intentions to yourself and to this friend; not communicating and instead hiding behind a facade of Chill rather than following the rules of Ethical Casual Sex; accepting scraps off his plate; giving away the power to determine what type of relationship is right for you; believing that you cannot move on unless he tells you it’s OK to do so.

The Patriarchy’s fault: the creation of easy-but-toxic predetermined roles hetmales and womyn can retreat into when faced with emotionally challenging situations; toxic male entitlement; the myth of The Chill Girl; the myth of The Psycho Bitch; womyn who feel they must live with the fear of societal ramifications for standing up for themselves, while hetmales by default, get the upper hand in the power dynamic while being asked to do the bare minimum of emotional labor.

So bbgirl, it’s time to get Unchill.

Are you being asked to come into your courage and do all of the emotional labor? Yes, but whatever.

Get what you want. Get Unchill:  



Any and all self-respecting behavior on the part of a womyn or femme that actively rejects or disregards any and all toxic, heteropatriarchial norms.


The advice, ultimately, is to put yourself in a vulnerable position, and tell him how you feel. Don’t try to sneak your feelings into his ear while he’s drunk at a party, don’t apologize for yourself. Because there is no need to feel shame. Three years is a long fucking time-- a lot of relationships do not last this long. So it’s time to get honest with one another. Maybe you’ll be pleasantly surprised.

Stop worrying about "losing a friend." Friendships are built on respect; if he's really your friend, he will welcome your honest communication and handle his own feelings with grace.  

But remember: if your feelings scare him, that’s his problem. If he tries to Psycho Bitch you, don’t let him. Just let him try to smear that bitter-ass-smegma-ass entitlement to fuccboiery all over you. It ain’t gonna stick. You’re too smart for that shit.

If he’s at all the parties, start going to some different parties! Or, just wave at him from across the room and know there’s nothing he can really do to hurt you. His bullshit projections are his business.

Find the least Chill path and take it. It’s the only way out of limbo.