on male friends

updated september 16, 2026

dear readers,

    i come to you from a cafe in montreal, conflicted and a little blue. recently, i witnessed the end of a very short-lived friendship. i say “witnessed” like i wasn’t the one repeatedly proclaiming to the world that it was over, with pride and more often than not, with an apprehensive melancholy. 

    i recently had a conversation with two of my longest standing friends about male friendships. sarah has always been able to connect easily with men in a platonic sense and has many male friends currently. myself and our other friend, maeve, have always struggled with that. this is ironic considering we both have brothers, but sarah is an only child. we were discussing the trials of becoming close with men only to have them eventually disappoint you, and “remind you that they’re a man”. sarah’s perspective is a great one, that having close trusting relationships and affinity with men is the path towards liberation for women, as well as men’s liberation from patriarchy and toxic masculinity. i- feeling very jaded, made some sweeping claim about my perpetual inability to have friendships with men, “it’s doomed”, “i don’t want to deal with their bullshit”, yada yada. i come to you today on this blog to explain a little of the context to this perspective, as well as to process the recent end of a friendship, and how my thoughts have changed. 

  

historical context:

    in eighth grade, around 13-14, my closest male friend dropped off the map. he stopped texting me, talking to me in class and asking to go to 7/11 after school (the favorite activity). it was around the time of covid, which coincided with our graduation and transition to high school. he was in a weird social position, friends with mostly girls but seemingly desperate to be accepted by the boys in our grade. his family life was turbulent, with an anti-vaxxer mom and homophobic dad (from what i heard from a mutual friend years later). when we were about 11, he had told me he had a crush on me, and i had rejected him. nevertheless, it hadn’t really impacted our friendship. we grew closer over the following two years, until he was my best friend. sometimes i wonder if my rejection hurt him more than i could gauge, and he had to stop talking to me to protect his heart. 

the flan, which i know i’ve posted before. as seen in the “four years and i still cry” meme. but it’s been six years.

    on the other hand, prior to his irish goodbye, he had tentatively come out to me by confessing he had a crush on another boy. this is another factor (i assume) contributed to his cutting of contact. maybe the homophobia in his home made him retreat into himself. in fact, i remember in high school hearing that he called it “just a phase”, and that he was now friends with the sporty, frat-bound boys. (indeed, he is in a frat now.) my heart always broke for him, because i feel like i witnessed in real time how his kindness was whittled down and his spirit dimmed. 

    in high school, it was always awkward to see him. i remember being at a party once in junior year and running into him. i don’t remember if we exchanged any words. he had obviously noticed my boyfriend at the time, who was standing next to me, and that seemed to make him a little uncomfortable. i remember him looking a little sad, and feeling brokenhearted after the moment. i still sometimes drive by his house when i’m in our home town. below, i’ve included the birthday card he wrote for me (i’m not sure what year), so you can understand how horrifying this situation truly was:

circa 7th grade

    in hindsight, there’s no animosity. but from the tone of this letter i think you can tell why it broke my heart for him to leave my life. i don’t blame him, and although we’ve never discussed it, i feel as though the aforementioned reasons give explanation enough. i still think about him often, and have considered reaching out to him. he still lives in boston, and is in a frat now. at risk of sounding cliché, i hold out hope that i’ll see him one day, out and proud, unafraid to be kind and vulnerable. in some ways, i wondered if i could’ve done more to have helped pull him from the clutches of toxic masculinity. i wish i could’ve lived with more humility, and inspired both of us to be more of ourselves.

friendships since then:

    this is all to say: i struggle to connect with men. i don’t have any close male friends and haven’t since eighth grade. i don’t have daddy issues, as i have genuine connections with male family members that embody masculinity safely, but since eighth grade, the closest i’ve got to a male connection was back in junior year, and even that’s a stretch. i reckon i was more of an emotional support outlet than mutually respected friend. myself and his other female friends were often aware that we were “mothering” or “therapizing” him. but still, i remember how he told me i was his closest friend, and the fact that we don’t speak anymore hurts a little more.

    i’ve felt close to a few men i’ve been involved with romantically in the past and called them my best friends, but that creates such a different atmosphere. oftentimes i interpret wanting to be friends with a man as romantic attraction, which is its own issue. and although i’m grateful for the experiences i’ve had with men and all that they’ve taught me, i’m equally grateful that i’ve forever chosen to move away from dating men. 

    i have one (cishet) male friend, R, which has been an interesting journey. when i first met him i thought i was in love with him. as i got to know him, i definitely developed love for him, but i quickly realized it wasn’t romantic. on top of this, it was tinged with being a mentor-mentee, quasi-fraternal relationship, so it quickly turned away from possible romance. we’re not as close as i wished we were, (a problem that, like most ailments in my life, is something within my control). he graduates this year, but i intend to soak up more of his wisdom and laughter before he leaves. 

    

    my love for R aside, a lack of male closeness still stands. it is evident that patriarchy has always gotten in the way of my male friendships. if their compassion isn’t destroyed by expectations of toxic masculinity, the gendered dynamic wrenches us apart. i think i can have good platonic relationships with men, but i’m not sure if it’s in my near future. 

the newest trial:

    recently, i thought i was making a new male friend. i’ll call him fred as an alias (palo alto reference, if you get it). i immediately felt that a gendered dynamic was visible between us- i felt myself adopt the kind of teasing (often misinterpreted as flirting) that i usually save for men, but spending time with him wasn’t difficult. we bonded through shared complaints about organizing and the people involved. (interestingly, this can be compared to R, with whom my conversations consist of wisdom about and love of organizing). fred leant me books and walked 2 miles both ways after a meeting just to talk with me for a while. we talked organizing and we talked theory. he told me about his childhood and we talked about music. maybe i was naïve in thinking that i understood him, or i fell victim to the “i can change him” mentality. 

    fred was the type to be borderline mean in a meeting, dismissing someone’s idea as blatantly bad, but then text me immediately after asking if he had been rude and how to improve himself. he once expressed that he liked hanging out with me because he thought i was more intelligent than everyone else we knew (i’m sure he feels this way about himself as well, and was just happy to find a conversation partner he found stimulating). evidently, i did not think this was a red flag at the time. i think the fact that he relied and confided in me made me overlook the fact that he truly was being mean regardless of the quasi-apology texts afterwards. a lot of the issues with social cues could be excused by him being very autistic and very russian. i never believed he was a bad person, and i still don't. i still think people dismiss him too easily and don’t care to get to know him, which i’m sure adds more reason for him to be mean to them back, but i also don’t want to keep giving him excuses for being an asshole.  

    long story short, this man still confuses me. he is strange and hard to understand, but at the time, i took pride in the fact that he was opening up to me, and that he showed me tenderness. perhaps in a selfish way, i was proud to be the only person to bother getting to know him and to be “approved” by him. we had inside jokes, we would be thinking the same thing and making pointed eye contact during meetings, and we would debrief after while looking at the stars and roaming the streets of santa cruz. i felt that our friendship was sweet, intimate, and understated (aka, i could hardly tell if he actually liked me or just liked the company). i should specify that he's gay and i’m a lesbian (and very seriously involved with my bae), so there wasn’t any weird romantic vibe. regardless, it was comfortable.

    until we were in the accountability meetings. in broad strokes, some of our collective organizational behavior was being guided by him, in relation to other groups we work with. some feelings were hurt and trust betrayed with multiple people, social repercussions were had. it was brought to our attention by some club members and we gathered to discuss what happened and how to move forward. it was myself, fred, another person who had been involved in the hurt feelings, and the club members who were facilitating. myself and the third person (both afab and conditioned as female, mind you) were quick to take accountability for our lack of communication and respect. we apologized, took the blame, and were ready to discuss how to move forward productively. unsurprisingly to some (yet embarrassingly shocking to me): fred denied any responsibility, instead explicitly blaming several other people by name, despite his primary involvement. most of this issue was semantic, so it wasn’t even a matter of him standing on principles. he just could not admit he was wrong or that he hurt people. it wasn’t just that he refused to apologize, he refused to admit that the hurt parties were valid in being offended by our disrespect. honestly, with his track record i shouldn’t have been surprised, as he hasn’t always shown the most attention to people’s feelings. it wasn’t even that he paid attention to mine, i just hadn’t been blatantly disrespected by him (yet). 

    i’m not really sure what the point of writing this big long post was, besides catharsis. besides expressing my grief about the loss i feel, not only of this friendship but the ones that came before it. it’s not necessarily that fred was a great guy or a great friend to me. it wasn’t that any of the other ones were especially great friends either, besides the boy from eighth grade and R. i guess this post is just a somber recognition of the ways patriarchy strip me (and men i could love) of connection and wholeness. 

    i have visions for male friends, and i think it’s possible. i intend to get closer to and stay close to my current close-ish friend R. i suppose this is the first beginnings of prayers that will let me experience connection and relationships free of suppression. like my eighth grade best friend wrote,  to make friends that “make me happy and push me to be the person [i] know i can be”.

    i think a lot about that conversation i had with sarah and maeve in montreal. i fundamentally believe in her point about holding men tenderly, but i also don’t want to find myself in a mothering role as i have so often. i feel fulfilled with my female friendships, and i feel completely comfortable leading a life that centers around feminine energy. however, i still yearn for friendship with men, and i think i’m coming out of my pessimism. 

    as of september 16th, i’m making another attempt at friendship with fred. i respect him to the utmost degree as an intellectual, and i cherish the moments of sweetness we’ve had. i don’t aim to change him, although i might bring up some of my past frustrations, but i might just be okay letting things lie however fits best. we are getting together this weekend after a summer of texting correspondence, to debrief life since and hopefully find some more stars to sit under.

in love and starry friendship prayers,

- ek