How to Convince a Woman that Sex is Bad: Part 3

How to Convince a Woman that Sex is Bad: An Instruction Manual for Men who Feel Entitled to Undermine Women’s Feelings and Desires




If I were a better writer, I’d write complete scenes and sneak in foreshadowing snippets, then callback to them in the future when their significance unearths. Or else I’d start writing as if we’d already reached the halfway point in the story and have flashbacks to contextualize the present on as as-needed basis. But I’m lazy, and wrote PART 1 and PART 2 eight months ago, and don’t really remember why I set up the story like I did back then (probably because I was so tired of hearing Dylan’s fuckboy shit that I didn’t feel like writing and reliving it). So I’m not going to hold off on the humiliating contents of BIG TALK (#1) any longer. I’m going to blow my load now and do the undoing of this relationship in chronological order. And I’m mostly going to include the sections that are pivotal to understanding the sequence of how everything unfolds, which I know is boring; in real life you never get to know which parts are going to matter in advance. You miss all sorts of critical cues. I missed all sorts of critical cues, which could have gone either way, and that’s why we are where we are today, my friends.

Oh, and if you are rereading PART 1 and PART 2 and are scratching your head, I made slight edits for clarity, ease, and exposition—nothing big and structural. I’ve decided not to be so precious about preserving my past. I used to be an obsessive archivist, fixated with producing memories that were unadulterated by what came thereafter. I had to cede control to work through the world as a working document, adapting to updates. In the process I became a less reliable narrator, so believe what you will. Here’s the thing with prevailing as a faithful archivist: I used to pour all 15 dollars per week of my allowance money into concerts (fleeting and indelible) and rarities: B sides, imports, soundtracks with a single important song. And now the internet exists and we all have access to Nirvana and Weezer’s entire catalogs, so my collection has been made worthless (like, I mean, I personally still break out the liner notes and smell them every so often, but no one thinks I’m cool!). I just, maybe have trouble seeing the value in holding on to anything nowadays. Maybe that’s fatalistic, and maybe the Smashing Pumpkins lyrics still stand, the more you change the less you feel.



Let’s rewind a sec, and I’ll take you through how I was feeling leading up to the BIG TALK. You will feel sorry for me, audience, when you learn what I was angling for on The Night of Lisa Who Fucked All the Dudes from Tinder, before it all went to shit, and my angle was rendered, well, more like a flat line. But nevertheless, I persisted.

I had that now immortalized conversation with my old friend who I went to the Japanese psychedelic show with and, by the way, that friend was Parker, of my pillow buddy fame. We allegedly talked about the trashlamp and how even though I felt a lamp was too high of a level of commitment I was happy about its symbolism because I felt really strongly about Dylan and was glad to know he felt like a permanent enough installation in my life that he could make my apartment into some found object interactive art piece, called like, “Wednesday mornings with Dylan” or whatever, because I think Tuesday is trash day. Cute, right? Except that’s not really what happened. Here’s a pretty accurate replica of the opening of my conversation with Parker. The stuff about the trashlamp was postscript.

“So… like… how bad is it if I want to get rid of condoms with this guy I’ve been seeing, and it’s not a monogamous situation, though we’ve been seeing each other for a few months and I’d be actually really surprised if he were sleeping with other people, but that isn’t really the point, it’s not that I’d never want to be monogamous with him, just that we’re going to have the conversations in the wrong order, I want to get rid of the condoms first, is that terrible? Am I going to fuck this up? Like, is it bad to have that conversation, forgetting about diseases and stuff, which I’m not really concerned about?”

Two nights after Kikaguku Moyo, I went to a [work] barbeque and people were talking about asking dudes to get tested for them, and how they wouldn’t fuck someone who hadn’t. One girl shared this horror story about how she went on a date with a guy in his late 20s/early 30s who had only gotten tested twice. The first time he had chlamydia. The second time was the 3-month follow up to rule out reinfection. Ew. Not about the chlamydia. About only having gotten tested essentially once in his 30-something years on earth. I shared with them, maybe too optimistically, “I’m about to have that conversation with the guy I’ve been seeing. We have to get rid of the condoms. He doesn’t know yet. I know he’s going to say he doesn’t have health insurance and doesn’t have money to get tested. But I’ll pay for it.” To which they replied, “Health Center 1: getting tested in Philly is free.” I wasn’t concerned about the logistics.

 Fast forward a single fucking night and I’m all poised to tell him I want him inside me and there’s just one knee-height hoop to jump through first, and then the shit about Lisa happens, and we spend the night adjusting our positions, calf-to-shin, elbow-to-shoulder, pins and needles-to-body parts, until we give up on sleeping, and then it’s a week until I have time to wade through the weeds with him and have “the talk” on my roof.



I scheduled BIG TALK (#1) for a few hours before I was supposed to meet up with my friend Tabitha at PEX’s Magic Garden Party at One Art Community Center. That way I had an out and a friend to decompress with if things went badly, and the timing just happened to work out that way. Originally I had planned to invite Dylan and offer to pay for his ticket, and initiate a conversation about whether it was okay with him if I paid for activities that were marginally out of his price range that I wanted his company for. But with things on the rocks between us, I had considered selling my ticket and was happy and relieved when Tabby got the night off work and could accompany me instead.

Dylan and I cut through the grass on my building’s rooftop garden and I spread my picnic blanket under the most steady, shady tree. The last time we were here was when we were on acid and everything felt a hair too highlighted, the breeze biting at our skin. This time we came equipped with booze to blunt the emotional discomfort. I think we’re convening to talk about how he wants to be with me but how things are complicated in his life and the circumstances are going to affect our relationship. Except he pulls a bait and switch from “My insecurities are not coming from my relationship to you but my relationship to feeling generally not in control of other areas of my life at the moment” to “I have some reservations about you.

He digs way back more than three months and brings up that during our first date I didn’t ask him any questions about himself. Which seems weird to me because he talked about himself plenty—about how he comes from a Catholic family of nurses and Trump supporters, he moved during high school and became a skater to make friends, he went to a public college and people in academia said snobby things to him about it, his childhood pet hamster died tragically at his birthday party, his student status had recently changed, etc. Maybe I didn’t inquire further myself because he was so forthcoming? Maybe he offered such standard, uncontroversial first date fare his stories didn’t lend themselves to deeper delving? Why would he keep dating me if I were self-centered as he seemed to be implying?

Then he goes all #notallmen on me, groaaaan. He complains about my calling him out for giving arrogant, unsolicited advice and labeling it as shitty male behavior. On our 3rd date I’d asked, out of curiosity, if he was voting in the local election, which I could have researched myself if I were so inclined. The next day he texted a photo of a political flyer and said his friends Rosie and Teddy, who are much more involved in politics than he is, recommended just voting for that slate. Indignant, I attempted to wave him off by sending a googledoc with rationales, compiled by someone I trusted as a source, and said I’d probably just use that voter’s guide thankyouverymuch. Besides, the flyer he’d sent only included “at large seats,” nothing about the contentious election in our district. Sure, he said, the flyer was citywide only. He added the caveat that so many candidates were running that there was some disagreement even among his “circle” and appended a guide pointed to by several people he trusts. As if I’d hold in high regard the 3rd-hand political opinion of some dude I’d hung out with only 3 times. This reminded me of when a dude I’d dated offered to edit my NP program admissions essays and later gave me “notes” on personal writing I’d shown him to, ya know, share something personal. He was neither a writer/editor nor a healthcare professional. I’ve seldom had a woman assume she was being helpful by sharing her unsolicited expertise, and I’ve seldom had a woman share her expertise without being an expert or providing a disclaimer.

Dylan also complained about my joking, also on our 3rd date, that some Nora Zeale Hurston tome he randomly plucked from his bookshelf and started lecturing me about was his showpiece to get laid. Like, bro, do you know how many fucking guys pull that shit to impress women? It’s not as if he related the book to me and my passions; it was like, “Here’s a big book I read ima tell you about… buzzword… indigenous woman!” Maybe instead of ragging on women for deeming male behavior problematic, he should have spent more time imploring men to stop being so awful so we don’t all assume the worst. And, as someone without the lived experience, he isn’t an arbiter of what constitutes sexism, benevolent or not; he doesn’t and will never have that barometer. So, sure, sure, women have to deal with men explaining things to them and pretending to be more informed and unbiased and it’s terrible, but when he does it, it isn’t part of a larger pattern; it’s just him misreading social cues and misjudging a situation, and he’s so not like that—he’s willing to learn from me! Ooof, fucking spare me from that #notallmen bullshit. Needless to say, I didn’t engage in that “reservation.” Not gonna apologize for call outs. Because drawing attention to oppression isn’t divisive; sexism, racism, and other systems of oppression are divisive. If he actually cares about being an ally, and is dedicated to showing up and not just showing off, he can deal with pushback from women. And, lol, funny thing about the election. Turns out we’d sent each the same voter’s guide. I’d say that’s a sign of compatibility. He didn’t see it that way.

It gets more odious than “not all men” though. Another reason he’s skeptical about us is an answer to an okcupid question that goes something like, “How do you feel about love?” Among the prospective answers are “I love it and want it very much” and “I just like to let things happen.” Because I picked the former and he picked the latter, I must have some kind of agenda that is incompatible with his life goals and circumstances. He doesn’t know where he’s going to be 6 months from now. He might have to take a job in China for all he knows. They go wild for Ivy PhDs there because Asians love brand names. He’s not going to consider me when he’s looking for jobs. I find this insulting, not because I believe I’m his priority, but because he’s stating the obvious as though it’s going to land as a revelation, implying that I’m some delusional woman who wants so badly to believe in the power of fairytale romance that I assume someone I met three months ago is going to restructure his life around mine. And, like, I know a thing or two about dating under uncertain circumstances. There were several junctions in my life when I was applying to programs or had already gotten into programs far far away, as I was trying to maintain some semblance of a social and sex life, and I didn’t just cease human contact because things weren’t going to be forever, Men were happy to continue dating me knowing there was a prescribed limit. I’m a big fucking girl, I can handle an untimely end. Most relationships end, anyway, regardless of geographical barriers. And, this is gonna sound fucked, but honestly a relationship that died of external causes would be a godsend to me, because I have never been in an adult relationship and a manless woman is a source of suspicion and social pariah. I’m worried that I’m eternally undateable due to my track record, or lack thereof. It’s the whole can’t get a job without experience, can’t get experience without a job conundrum. No one would attribute the end of things upon the introduction of an ocean between us to my incapability of maintaining a long-term relationship; they would commiserate about the cruelties of academic life. Loss is sympathetic. He would have been a great starter boyfriend. Lol, and a month later, after things really go to shit, my friend will be like, “Genie, you don’t need to stay with this guy to build your resume.” But sort of I did.



“Don’t you want something stable?” Dylan asks me, still suspicious about my answer to the okcupid question. “No!” I insist. Stability is such a nebulous, ableist concept. It implies that the world is a predictable, safe place. It denies that relationships are dynamic interactions that adapt or destruct, rather than static pairings independent of time and space. And it seems like Dylan is willfully ignoring what he knows to be true about my history: that he is far from the first person I’ve met on okcupid. I’m not with him by default or because I’ve succumbed to ennui. I’ve been out with approximately 25 dudes in the past two years since moving to Philly. None of them captured my interest, unless you count a fortuitous friendhip pairing. I’ve fucked approximately 10 in that time span, between internet dating and real world connections. And, I didn’t tell him this at the time (or maybe I did?), because I didn’t want to creep him out, but he’s the only one I had sex with more than once. What if I let him go, because he may move to China six months from now (which is an improbable, worst-case scenario), and he ends up staying in Philly after all? We would have wasted time when we could have been together in the service of staving off pain. What if by the time he moves we’re in a serious relationship and I want to go with him? Lives can change in a short amount of time, which pretty much anyone with a chronic illness agrees is not a romantic concept. What if we’ve broken up before six months from now anyway, so it’s a moot point and who fucking cares? I can’t make decisions based on a future nobody can predict. What I do know for certain, based on bountiful past experience, is that I’m picky AF and a niche market, and okcupid is wont to become an emotionally spendy time suck, where the sex and superficial connection generally isn’t worth the effort and fallout. If I pass him up because it might present a challenge later on, I’ll most likely go through 25 more guys before I land on one who clicks. And does hopping from stationary dick to stationary dick really constitute “stability”? I should think not!

“But don’t you want someone more stable than me?” Dylan reiterates. “There are tons of guys in Philly, who at very least are still going to be in Philly next year.” Stability, stability, if there were ever a time in our relationship where future Genie should have swooped in and issued a warning it would have been here. I would have keyed in on that word and advised, a la Maya Angelou, “When someone shows you who they are, believe them the first time.” Now here is where I get heated about his emergent Seth Rogen-style manchild fuckboy bullshit. It wasn’t as if things started getting shaky between us and in an attempt to decode, Dylan flipped through my okcupid profile and was like, “A ha! There’s the disconnect!” He had fucking scruntinized my profile and made frequent references to passages so obscure I had forgotten I’d included them. He was more fluent in my dating beliefs and goals than I was. Just so we’re clear, here’s what was in the body of my profile, under the “What I’m actually looking for” and “The most private thing I’m willing to admit” sections:

“What I’m actually looking for”

  • Want: a primary partner who is guileless, eschews social formalities, respects desires and boundaries, fosters intimacy at the risk of vulnerability. Friends are nice, too! Bring me to shows and readings with you.
  • Need: a service top, unambiguous communication, keenness to defer to women as arbiters and experts.
  • Wish: ppl didn’t use “fun” as a proxy for disposable sex.

“The most private thing I’m willing to admit”

  • I’m surprisingly traditional when it comes romantic relationships. Though I only enjoy unconventional people. I’m looking for something monogamish, a relationship structure that okcupid doesn’t yet recognize and one that has the foresight to accommodate for life’s conditions being unpredictable and in flux.

Does it sound like I expect a fucking fairytale with some clean-cut cookie cutter, and surprise he can’t provide that? Is it possible that he didn’t know what he was getting himself into? Look, people are looking for different things on the internets and you have to respect that. Sometimes you come across a profile and someone looks otherwise compatible (they love thrift stores and records and art–yay!) but turns out they don’t want kids so you keep it pushing. Sometimes you are seeking the same life landmarks but you are not each other’s person so you keep it pushing. But you can’t date a 35-year old woman who is exceedingly transparent about what she wants and say all this wishy washy bullshit about where you are in your life—which has literally nothing to do with what she is to you and is just a fugitive fuckboy excuse—and treat her resolution like it is a character defect. I will not have someone insinuate I’m some basic sheep who needs to achieve status symbol facebook-ready milestones to feel accomplished and on track with her peers, especially when my life choices have demonstrated basically the opposite. Like, fuck him so hard for saying that if I’m looking for something stable, I should look elsewhere. Give me more credit. I was a fucking academic myself before I switched career paths. I know what position I’m applying for. I’m not interested in some boring dude with a marketing career, pension, and picket fence. Even if I could live more comfortably that way or whatever.

And like what the fuck does he know about stability, anyway? Does he have any idea what my life has been? I’m 35 and I’ve never been able to support myself financially, which fucking sucks, and not because I chose a career that wasn’t lucrative. I haven’t had the foresight to know whether I’m going to be alive or seriously crippled, nevertheless whether my life will magically coincide with someone else’s. I worry all the time about the what ifs, like what if I got really sick and had to take more time off school and my record would once again be marred and I had to work my way up from the bottom, what if I was in a relationship and my illness overtook me and the person I allowed myself to depend on left me or even worse I felt guilty all the time about being a burden and spoiled things, what if I went on endless job interviews and no one ever took a chance on me because forever a liability forever alone. So if that was what I wanted, because I was so tired of being terrified all the time, he shouldn’t fucking judge me for it. Stability isn’t some superficial thing for unimaginative normies. But I don’t need the stability of a guy who has been at the same job for 15 years and will take care of me financially; I need the stability of knowing that a guy wants to be with me. That someone is going to be kind and consistent. And that’s a reasonable expectation.

Let’s acknowledge how gendered this “what you’re looking for” paradigm is and how much fucking gender privilege he has in our dynamic. He could be a total washed up loser at 50, someone who peaked at 25 when he published three articles, and still have impressive, stable 35-year-olds lined up to marry him. I don’t have that luxury. I’m basically expired in the eyes of society. And I don’t even have the main biological clock constraints that most women have since my reproductive future is on ice. It took me a long time to build courage to be emotionally honest and direct with men even when it’s considered deeply unchill and makes women unlikeable and leaves us open to accusations of desperation. I love Alana Massey’s essay Against Chill:

“Chill has now slithered into our romantic lives and forced those among us who would like to exchange feelings and accountability to compete in the Blasé Olympics with whomever we are dating. Oh, I’m sorry, I mean whomever we are “hanging out with.” Whomever we are “talking to.” Chill asks us to remove the language of courtship and desire lest we appear invested somehow in other human beings. To even acknowledge that there might be an emotional dimension to talking or dating or hanging out or coming over or fucking or whatever the kids are calling it all these days feels forbidden. It is a game of chicken where the first person to confess their frustration or confusion loses.

But Chill is not the opposite of uptight. It is the opposite of demanding accountability. Chill is a sinister refashioning of “Calm down!” from an enraging and highly gendered command into an admirable attitude.”

I’ve always said that NYC dating is a contest of pretending to give the fewest fucks—an emotional standoff. One must affect aloofness, with the stony precision only a true New Yorker can muster, to win. The catch is, winning means saving face but gaining nothing. And I’m fucking tired of that bullshit. When you fail to acknowledge your feelings for people, they can never be reciprocated and you are always left wondering what could have been if you only let your guard down and put yourself up for auction. Having feelings for other people is not embarrassing, because having feelings isn’t embarrassing, it’s a basic part of human nature and it should be celebrated! I’m not going to let some 35-year-old fuckboy, who has been waffling in a PhD program for 10+ years and refuses to make any kind of decision—because he is so chill that he just likes to “let things happen” and because he estimates mundane life transitions to be seismic shifts but really because he is paralyzed out of fear of failure—undo my emotional progress. Like Alana Massey says, “Indecision is not a noble virtue.” Being suspended in state of manmade uncertainty is untenable; it puts me and only me in a compromising position and is less fair than flat-out rejection. Imagine enduring an emotionally toiling trial to be hammered with the verdict of hung jury. It imbues every subsequent time we hang out with artificial importance, as if each encounter is subject to diagnosis and prognosis. It creates an unequal power dynamic, nominating him as the sole keeper of the terms and conditions. It prohibits me from acting based on defined knowledge. Again, Alana Massey, “putting labels on things are how people find the exit during a fire and make sure they’re adding vanilla extract to the cake instead of arsenic.” Refusing to define things is a fucked up form of control that passes for latitude.

 And, yes, women aren’t a monolith so it’s maybe plausible that he could find a woman who put the “let things happen” answer and isn’t lying. But most 35-year-old women aren’t just sitting around jerking off waiting for dudes to grow up so I’m guessing that like 95% of women who tolerate his bullshit are just lying because they’re scared of rejection and being completely alone. Which I’m quite obviously really not. And, by the way, “I like love and want it very much” or however it was phrased and “I just like to let things happen” aren’t fundamentally incompatible; they aren’t mutually exclusive. I’d like to be in a loving, committed relationship, but I’m not forcing things with people I’m not really into; I’m letting them evolve organically. Like, duhhh, if I wanted to play by the rules and cuff some dude or whatever you kids are calling it these days I wouldn’t have been single for the past decade. It isn’t as if I truly believe I’m undateable. Thought I definitely have irrational insecurities about that. A certain breed of nerdy boy, the kind who looks like his mom still dresses him, finds me enticing and would be proud to parade me around (what a score!). I could easily tone it down and be a bit less weird and snag one. But I don’t want to me less weird. I want to be with someone who is compatibly weird. Perhaps someone who thinks it’s clever and not gross that under okcupid’s “I spend a lot of time thinking about” heading, I put “Body horror grindcore band names like Frank Blood and the Fecal Occult.” Perhaps someone who thinks it’s precious and not creepy that under okcupid’s “When I die, I will” heading, I put “Live on as disembodied organs in another human’s body. A morsel of cadaver is lodged in my spine. It was listed on my itemized receipt as an add-on item, like a condiment. A morsel of cadaver, a dollop of sour cream. I want to be someone’s condiment.” Definitely someone who, like Dylan, invited me to an art show consisting of natural artifacts that had been destroyed in elegant patterns by invasive species. Definitely someone who, like Dylan, sent me an article about sacrificial bugs exploding then anxiously obsessed over the semen-evocative title.

I’ve been exceedingly flexible about what I’m looking for based on the person I’m presented with. From okcupid and the real world, I’ve acquired friends, and friends with benefits, and fuck buddies and fledgling romantic relationships, in many iterations. The next new person I hooked up with after Dylan, also named Dylan (lol), articulated his philosophy about dating in a way that was so succinct and neatly congruent with mine that I’m going to share it:

“What I’m actually looking for”

  • “Ultimately I’d like to find a long-term, committed partner. But along the way, I’m open to different types of connections depending on what feels right with a particular person, which could include more casual relationships, hook-ups, or friendships. Most important for me is open and direct communication about what each of us is feeling and wanting from one another.”

Dylan number two delivered: we communicated openly about what was working/not working and what we wanted. We weren’t each other’s person, but I didn’t feel misled.

Regardless of what I may be looking for or open to in general, my relationship with Dylan number one was never structured as casual; it was always set up like we were exploring the possibility of a romantic relationship. And he’s the serial monogamist, for christsake! One of the aspects of his profile that attracted me was his answer to the question, “Are you looking for something casual?” He elaborated, “I’m open to it, but not ideally.” A bit similar to Dylan number two’s sentiment, right? I gathered that he wasn’t seeking something random, fleeting, or circumscribed. And everything about our relationship up until the night of Lisa the Slut reified my assumption. See, the problem is, he spent three months acting very boyfriendly. There is no fucking reason to invest so much time in someone, and when you fuck up and are cornered into a “where is this going conversation,” suddenly drop it on her that what she was seeking was always implausible; you never respected her and were always skeptical of her genuine affinity for you. It’s fucked up and super dishonest and like OMG why would he do that!? What could he possibly be getting out of it? Of course I have no idea how he behaves with other women, I only have myself as context, but it seems to me like even if he is theoretically “open” to the possibility of having a casual relationship, he doesn’t know how to run that script. And speaking of someone whose actions and words don’t align (see: Lisa the Slut who made big gestures but didn’t express feelings verbally), it’s damaging for me to be in a situation with someone who acts like my boyfriend but lets me know in no uncertain terms that he doesn’t want to be that person, at least not yet, and thinks what I want is stupid. He can’t have it both ways; he can’t have me at his convenience and toss me aside when he feels scared.

So, no, I was never dating him because I’m some desperate geezer who needs to tie a man down before her ovaries atrophy and her boobs graze her waits, or because he fit some generic prototype of what a man should be so he’ll do!! I mean, on paper he’s fucking terrible. He’s been in the same program for longer than you’re technically allowed to be; he talks about his high school days like he’s some jock who peaked at puberty; he has no money and his monetary prospects are minimal even if he meets success and publishes an acclaimed book; his family is Catholic and doesn’t believe in women’s rights; he has a dad bod, is balding, and his face is objectively less attractive than mine (but I’m attracted to him and his body has always felt just right in a Goldilocks and the Three Bears way so who cares); and yeah then there’s that minor detail about not knowing where he’ll be in six months. But dating isn’t about meeting someone who ticks all the boxes (sorry to get all Carrie Bradshaw on you). It’s about meeting someone you like being with enough so you can get caught up and forget about what you’re “looking for.” And I’m stealing this from some internet stranger (named “Weaver”) on okcupid because it’s fucking beautiful (and if this is yours and you want to be credited in some other way or made more anonymous obviously holler at me):

“the thing about it is i say all this stuff on okcupid about what i’m looking for, but the truth is what I want is the person who’s the exception to everything

the person who makes the specifics not matter, the person with whom the future is not at all clear except that i know i want to share it with them

that’s part of what sucks, you can’t type character traits or values or life goals in a search, you kind of just have to do your thing till such a person magically appears

at which point they probably upend your whole deal

but that’s exactly how you know they stand out from all the rest”

The word “ineffable” comes to mind. But the thing is, even if you can’t verbalize the specific qualities that make someone that person for you, it has to be explicit that you are designating them that person, and they you. Dating is about meeting someone you feel solid enough about to allow them to destabilize you; it’s about picking the person THEN letting it happen. And, so, his complaint was ultimately ironic, because I was the one who was open to LETTING IT HAPPEN. Not because I was naïve about his flaws and didn’t have reservations of my own, and oh god did I ever have reservations. But because I don’t believe that living in what-if worst-case scenarios and halting everything with anticipatory anxiety without a plan for resolution is qualitatively more secure than jumping in the deep end. I guess it’s a tradeoff between traversing the unknown and slumping into shit, and after years of the latter the former seems like a better deal. It’s funny, but not haha funny, every time he referred to my being “vulnerable” with him, it felt viscerally wrong. Sharing my positive feelings for him didn’t make me feel vulnerable; it made me feel hopeful. After all those years, playing chicken made me feel cowardly and pathetic and like I was stunting my growth in the service of false safety; I used to joke that that I should hang a sign at the entrance of my vagina that read, “Abandon hope all ye who enter here.” At least that way it would have been clear to everyone that they were smashing against a wall.



Our conversation veers into past relationship territory. We speak of funny mishaps, situations that poked at our boundaries, those we we’re still reeling from and that left us permanently altered, those that might shape the way we approach and treat future partners—questions, regrets, and things left unsaid.

He tells me about the time he went on a date to some party with a spanking station, and how he told his date he’d catch up with her later since he wasn’t comfortable with that display and finds S&M to be hilarious rather than sexy. He tells me about how one ex was a black belt in some martial art and insisted on fighting him before every time they fucked. He goes into a great amount of detail about the Lisa/Sandy saga. The way he pitches it is concerning in his lack of insight into his contribution to the dramarama and his impulsivity in following a woman he’s hooked up with once to another continent for her work.

I find this willfully ignorant attitude to be common in people who practice “ethical non-monogamy” or are in “open relationships.” A note on the term ENM: my main objection is it’s supposed to connote moral superiority. Like, if someone lists “nonmonogamous” in a dating profile, it’s obvious that they aren’t advertising being a cheater. So prefacing it with a value descriptor is redundant and nothing but a holier-than-thou affectation. Many people in such situations, and I find people in the Burning Man community to be extreme offenders, cast nonmonogamy and its participants as more “enlightened” in their lack of possessiveness and nonadherence to social norms. And this is a tactic that sleazy men, who weaponize the term “sex positive,” employ to guilt/pressure women into doing things they’re not comfortable doing. Like, I can’t even tell you how many guys have tried to convince me that I’m a prude (lol) and unevolved as incentive to fuck them, as in fucking them was some shortcut pathway to feminist liberation. When, like, people are allowed to have preferences and honor their preferences and no relationship structure is boundless or imbued with morality; it’s how you practice within the structure of the defined relationship.

Which brings us to the next point about “ethical non-monogamy.” People often treat such an arrangement as an excuse to ignore multiple people’s feelings (usually in a gendered way). An absence of consent is inherently unethical but presence of consent doesn’t necessarily make nonmonogamy ethical. No one can predict how they are going to feel when their partner has sex with other people. Being hurt by or feeling complicated about the situation doesn’t make them the bad guy for voiding a contract and doesn’t mean they entered into it in bad faith. It’s never okay to continue in an arrangement that is actively and continually harmful to a participant under the justification that they voluntarily and mutually agreed to it upfront. Consent is a working document. Feelings change. Complications surface. And it is up to both parties to recognize that and adjust. I think this is a concept a lot of men struggle with, and I hear this resistance a lot in discussions about consent and sexual assault—our shitty litigious society is largely to blame for making men defensive and casting it as a black and white issue with a perpetrator and target. There needs to be nuanced discussion, beyond blame, about how sex is intense and people can be harmed and that harm deserves acknowledgment and repair even if the perpetrator of harm didn’t knowingly disregard or trample the person who got hurt. More on that in a future post.

Anyway, the way Dylan described this clusterfuck in which he and Lisa agreed to be in an open relationship but never talk about it (it was a “don’t ask don’t tell” joint)—and how he didn’t understand why she “had to” fuck so many dudes from tinder when they were having sex regularly and she was also having sex with her roommate Tony, and how it was hypocritical and unfair that Lisa was upset by the romantic nature of his relationship with Sandy, and how he had promised Sandy more even though it was never realistic because all they did was party together (“she was wild; sometimes she did a little coke”), and how now Sandy refuses to talk to him because she felt deceived, even though Lisa knew about Sandy and Sandy knew about Lisa so everything was above board and copacetic—made me fear for his ability to be accountable. Maybe I wouldn’t have found his behavior to be a red flag if he were 25 when this happened, because people do stupid shit when they’re figuring things out. Or even if this went down last year and he felt dumb about it and attributed his irresponsibility to acting out at the culmination of back-to-back long-term relationships; I consciously make stupid decisions too. But that was very much not how he processed it. He acted like wooah, some clusterfuck randomly befell him, a superchill dude, because women are wild and Sandy was the one who was doing all the drinking/drugging and Lisa was the one with fucking all the dudes. When in fact he was an active, heedless participant and left a lot of angry women in his wake. Reminds me of a quotation from Jade Sharma’s Problems (RIP, JADE):

“Behind every crazy woman is a man sitting very quietly, saying ‘What? I’m not doing anything.’”

Look, categorically I don’t trust people who are in “don’t ask, don’t tell” situations. An agreement to not discuss potentially heated/loaded things is the epitome of emotional dishonestly, even if it’s allegedly in the service of preserving situational honesty (i.e. we’re not lying about fucking other people because we’re transparent that it’s is an option). I mean, it was fine when Dylan and I were gauging whether and in what capacity we wanted to be together. But beyond that, there’s a slew of reasons why this configuration would have been impractical and unhealthy on a continuing basis. First, there is a clumsy concealing of details when your partner asks what you’re doing on a particular night and the answer is “hanging out with another dude.” Next, what happens if that other dude impacts you negatively and you need someone to talk to but can’t lean on your partner because “don’t ask, don’t tell.” Finally, how do you explain when complicated feelings from your sidedude expand into your primary relationship, and your partner attributes whatever weirdness is happening to the functionality of your relationship (i.e. thinks it’s about them) and erroneously questions how things are going.

I need a partner who can communicate directly and approach challenges head-on when things don’t feel quite right, not someone whose communication ends at managing terms of service and whose orientation is, Shrug, they signed off on it, what did I do? Like, sure, Dylan showed up when he threw a wrench in things, and he continued showing up very reliably. But was he doing just enough damage control to keep me around? By the end of the night I would start to worry that he reveled in ambiguity and discontent. He’d told me the night of Lisa the Slut that Lisa texted him every day and he wasn’t interested but didn’t say anything because she should be able to “take the hint” and he doesn’t want to “have to break up with her again.” As if he is doing her a favor by stringing her along and keeping her around on his terms, while ignoring her suggestions. I don’t want a relationship built on hints and suggestions; I need transparency. Fuckboys like Dylan refuse to act definitively because they don’t want their decisions to reflect badly on them. They fail to commit their dissertations to paper because they are afraid of failure. But inaction is a form of action, and it is neither commendable nor sustainable.

I tell Dylan about my most dramatic break up of all time, with that vengeful dweeb of a lawyer who threatened to sue me for intellectual property theft for posting his artless cruel emails on my blog even though I hadn’t included any identifying information and we don’t know any of the same people, since he had no friends. I referred to him in ubiquities like “28-year old Jewish lawyer,” i.e. 1/10th of Manhattan. When I initiated the “I’m not sure if this is working” convo, he told me the sex between us was “mechanical,” which hurt my feelings because guys always insinuate that I have no feelings and I wasn’t sure what he expected of me so early on in our relationship in terms of tone. As we ruminated on whether we could work things out, he told me that the first time we hooked up I gave him the worst head he’s ever received, and that he found sex with me “odd and degrading” since I gave him instructions and “fucking me was like his mom telling him to do his chores” (he hated his mom). It was so intentionally mean and outrageous that I thought it was funny and sent our convos to all of my friends before posting them for public consumption. Once things got contentious (what did he expect!), he concluded that I was just upset to find out “[I] wasn’t so good at the only thing that defines [me]”—ouch!

In fact, I was upset, not because someone didn’t think I was a sexual genius, but because I felt duped. J.D. Douchebagg, J.D. explained the reason he hadn’t given blowjob feedback, when I’d asked explicitly for it multiple times since things took longer than I’d been hoping, is that women are sensitive about that sort of thing. As if it was better to allow me to continue to humiliate myself and for him to accrue resentments than to speak up and attempt to correct things. Did he think I relished doing a bad job or I was such a disaster it was unfixable? The odd thing is, the way in which he formulated his complaints about how I like to conduct my sexual encounters (i.e. with instructions so my partner could get things right), indicated that he believed it to be a universally understood truth that my sexual style was revolting, and anyone who acted otherwise was only humoring me. He acted as if he were fucking me as a favor and must have enjoyed hoarding resentments to have something to hold over me when things deteriorated. But this was no favor.

Amazingly, I can find people who enjoy fucking me and actually prefer how upfront I am about my wants—it removes the clumsy guessing game of getting to know a new person’s body and reassures them I’m sincerely pleased. In withholding his gripes, J.D. Douchebagg, J.D. was keeping me from finding a mutually rewarding situation; it felt selfish. What really really bothered me about this situation, though, what shook me to the core, was how violated I felt. The entire time we were fucking I assumed it was mutually enjoyed (why else would he keep doing it!?); I don’t want to have sex with people who don’t want to have sex with me. I wouldn’t have consented to it had I know. Also, he told me he’d offered to cum on me and not complain about it—even though he thinks cum is “hot, sticky, and smells bad” and doesn’t want it anywhere near him—because he finds it rude when a dining partner directs “ew” at something he’s eating. But that’s not how sex works. Again, sex is a mutual experience; I can’t enjoy myself if the other person is grossed out by an act and putting up with it to please me. Cum is high on the list of things I’m unwilling to negotiate about sexually and the vast majority of men are not disgusted by their own semen; why should I stay with someone who is fundamentally incompatible when my preference isn’t so niche that it would require a fetlife account to conscript an appreciative partner?

And, quite obviously, I was horrified that a guy who I’d been having more than just sex with for several months considered sex to be the only thing that defined me. Sure, how I present my sexuality distinguishes me from most other women, but I’d like to think I’m worth more than that. Of course, by that point I’d assumed he was just being as mean as possible, but still, that part actually wounded me.



It felt humanizing to joke with Dylan about milk spilled and messes made, like we were past the point of keeping up appearances. But as our conversation was winding down and the time I was supposed to meet up with Tabitha was bearing down on us, I was at a complete loss. We had managed to warm up to each other but obfuscate what we *were* to each other. Things felt even more distant and misaligned, like we were only separated by a semester in graduation dates but ten years apart in life experience. I couldn’t believe he had gone from “I thought we should talk about where things were going” between us and “I’m down for something more serious” to “All I can [commit to you] is to keep getting to know each other better” and [insert a bunch of fuckboy excuses I hadn’t heard since my early 20s here]. Seriously, he said this “getting to know each other” line like it was a great sacrifice and concession. Or maybe like when administrators “offer you the opportunity” to work for free. Why would someone instigate a conversation about how they wanted things to continue as is? Like, we were already continuing to get to know each other better, as was implied by our not ceasing to hang out, so what was the point of announcing it? In such a way as to get my hopes up. As to suggest something more was coming. And that I should stick around for it. I felt taken for a ride. Our relationship had veered out of focus.

I needed to recenter our conversation around its initial purpose: to define the relationship. So, as a last ditch desperate fucking effort, I gave him a projection for how things were going to go if they continued haphazardly as is. And, in retrospect, I’m horrified by how I framed this, because ultimatums are the death knell of relationships, but really a relationship is over once it gets to the point where you have to threaten to end things if someone doesn’t get their shit together and step the fuck up. I already happened to have a convenient point in time plotted out, though putting the pin in the map prior to our BIG TALK had been entirely incidental, as in, the opportunity to travel with Clyde arose when it did impervious to the trajectory of our nascent relationship. Way back when, I genuinely wanted to consider Dylan’s future feelings; now I had to redirect his attention to this arbitrary time limit that had to be set if I weren’t to get jerked around indefinitely.

When I’d fielded how Dylan would feel about my prospectively going on a vacation with another guy further along in our romance, I saw the junction of before and after as positive marker—something to look forward to, rather than something to avoid bumping into. I had it in my mind that if we were still seeing each other and things had progressed in step, I would be grateful not to be tempted by Clyde, or at least would be happy to not act on temptation. It would be a test of how magnetic my pull for Dylan, and the restraint seemed decadent AF. Honestly, when I’m having regular sex with someone I’m into, I’m not spending a ton of time fantasizing about other dudes or going out of my way to attain armfuls of dick. The restraint would be less about my deprivation in refraining from Clyde and more about the longing engendered by our geographical partition. I remembered how horny I got during my week in Colorado, when things were just starting up between us, and we texted about mate competition and not showering to prep for our future fucks. That anticipatory excitement would be compounded months later, once our relationship had developed, and the contrast between Clyde and Dylan was laid bare. I would spend a week scenting sex on Clyde, and it would remind me that all he ever was to me, was a fragrant topography of flesh and flora. I had chosen Dylan, even though his scent was neutral.

By the end of the evening, the idea that we’d be anything to each other by the end of the summer was remote and risky in a decidedly unsexy way. So I summarized the state of affairs as a stale practicality, “Just so you know, if we’re not in a monogamous relationship by the end of the summer, like by the time I go to Hawaii with Clyde, I’m going to be bored.” He got it. Then, fuck it, we were already so far gone, such a lost cause, I had to say the one thing I had meant to say before I was backed into this defensive corner, “And also… I really hate condoms.” It was a functional reason for monogamy, among all the nicer mushier ones. What I like about raw sex, besides it feels good, is that it accelerates emotional intimacy; I had been ready to entrust him with the power to hurt me and to let the pain feel personal and cut deep, as of the time we tripped on acid together and became neon gnomes in a domestic forest. Only now it was blatantly apparent that condoms were the least substantive barrier to our bonding. The noncommittal things he’d said and how they reversed my feelings for him nearly voided my request to ditch the protection. A month and a half from now, if we weren’t operating as a cohesive unit and I couldn’t be granted the privilege of having his trashdick directly inside me, I was super fucking gone. But what kind of loser even pines for this manchild’s trashdick? Has it really come to this, at age 35, in the year of our Lord 2019? Like, I’m begging for a dickin from some dude who “just likes to let is happen”!? Oh god. How humiliating.

I wasn’t sure whether I wanted to see him again, tbh. TBD. So I invited him upstairs. Because I was fucking horny and I’m bad at life and after all the shit he said I thought, just in case, might as well shake the last bit of sex out of him I can get. I’m pretty sure he saw it as conciliatory and I saw it as cya sex. But it wasn’t bad, and I didn’t feel bad about it, lol. He’s the one who pushed us into this perfunctory purgatory where everything was touch and go. And, for the first time with him, I felt wanted. There was a sudden sense of urgency, maybe because he knew I needed to change my clothes and slather on make up and head out soon, maybe because emotional tumult fed us and begged for tidy chemical resolution, maybe because he knew our connection was precarious and ephemeral and he needed to get it in while he still could. Whatever the reason, I didn’t give a fuck; I wanted his sloppy cock inside me before I broke character and came to my senses. He shoved me against the wall in my foyeur, hoisted me up, and deposited me on my back across my mattress. We grabbed handfuls of each other and unlatched our clothes. I swung my torso over the side of my bed to reach for the handle of my built-in condom drawer. “Hold on,” he said, and I popped back up, dropping the shiny wrapper on a deflated pillow beside him. “Do you wanna try it without a condom this time?” he asked. I couldn’t fucking believe it. Here he was offering me The Holy Grail of Sex. The one thing I had wanted. And now I didn’t even really. Because the circumstances had changed and I didn’t need to have unprotected sex with this trashhuman I was mega wary of and probs never gonna see again and it’s totes not worth the risk for a one-time thing. But how could I resist?

Everything else had gone so terribly. I felt dejected. And he could fix it in one fell swoop! It felt too good to be true. I flashed back to a few weeks earlier when we were on acid and he looked like a benevolent gnome with irradiated glints of hair and skin, and the finest features of his dick were accentuated and I wanted it in me so bad I could practically feel it prying me open as I tugged on it. I pictured myself pancaked on my back against the sheets, legs pinned together, with him looming over me. With each thick breath, his dick twitched through the arc of my palm, inhale and exhale, shallower and deeper. I couldn’t ask for it then, now matter how bad I wanted the approach to keep sliding before swerving to retreat, because we were on drugs and that would be an unfair consent process.

“Do you get tested, ever?” I asked, this time. Pretending to cobble together what play-acted as cautious but was more like resigned. Instead of the centimeters between us collapsing like an accordion, as our bodies pumped in concert, our timeline compressed to the present. “Yeah, of course,” he said. “Like when?” “After Lisa… So only Anna.” [As in, Anna was the only person he’s slept with that since getting tested.] “Me too. I’ve only slept with one person since I got tested in December. And only once. He seemed low risk and we used protection.” “Yeah, Anna and I always used protection too.” She was a “lesbian” before she dated him (though I’m not sure she identified as such since she’d dated a transman), so she seemed very low risk. “Okay,” I nod. “I’m fine with that. So, do you want to?” “Yeah, I mean, if you do.” I brushed the shiny wrapper off the side of the pillow, and mounted him. He flipped me over and really rammed into me. It would have seemed too good to be true, except, as Kevin Kelly says in 68 Bits of Unsolicited Advice, “Anything real begins with the fiction of what could be. Imagination is therefore the most potent force in the universe, and a skill you can get better at. It’s the one skill in life that benefits from ignoring what everyone else knows.”



I meet up with Tabby at the party and spill everything, how things seemed to be going well until he turned into a total fuckboy, and oops I had unprotected sex with him. Which I wanted, but not like that. We discuss birth control (she also works in sexual health), and how maybe if I were going to continue fucking him without protection, I’d switch to a more reliable method. Perhaps a NuvaRing, which only has to be dealt with approximately once per month, not daily like the pill. But I’m for sure not putting anymore effort into “getting to know him better,” as he’s projected for the foreseeable future. If he wants me, he can pursue me. I’ve had enough of taking initiative only to be hemmed and hawed and talked in circles until I’m dizzy. I ask if I’m totally insane and naïve for even considering seeing him again, and what Tabby tells me might be the tipping point. She says, “No. I’m really impressed by how much you’re communicating with someone you haven’t known for very long.” And it’s true, the communication does feel really good and calm and considerate. He doesn’t shy away and avoid conflict, which always ends up hurting me more in its implicit rejection. Showing up is a form of care within itself; it connotes that your feelings are valid enough to be worth engaging with. But here’s the thing: someone can show up repeatedly after they do hurtful things and field your feelings and it does show a certain amount of care and possibly even respect, but if they keep doing those things knowingly, it harms you regardless of whether they feel sorry for the pain they are causing. It chips away at your self-worth.

The next afternoon Dylan and I have the following conversation about boundaries:

Me: To follow up on last night, if you wanna keep having unprotected sex with me and you’re sleeping with other people, I don’t need to hear about it or want to hear about it, but you do have to use protection with them. Fair?

Dylan: More than fair. That was the first time I’ve had unprotected sex in a really long time. Like years. Just so you have a better sense of my habits.

Dylan: I assume that you’ll follow that rule too. Right?

Me: Ok good to know

Me: Ha, yes

Dylan: Also, I keep thinking about last night and getting really turned on

Dylan: Not just because there was no condom, but it overall felt really good for me

Me: I liked that you were a little more physically dominant than you normally are

[he’s such a natural bottom, groan]

Dylan: Noted

I can’t believe it’s so easy. Sometimes he’s so reasonable I’m stunned, and concurrently puzzled by how difficult past partners have been to negotiate with, how resistant they’ve been. Like really this is all that it took to get what I wanted? Unbelievable. Maybe this is how things look when you’ve found the right person. Or maybe this feels resolute compared to how wishy washy and fickle he was last night. Something doesn’t quite add up? Oh, and this is besides the point, but we’re not having sex with other people. I’m pretty sure of it. Which makes it even worse that he can’t commit to me.

After that, I scale it back and become a passive participant in our relationship. I have no expectations. If he wants to pursue me, that’s his prerogative.

This entry was posted in how to convince a woman that sex is bad: part 3. Bookmark the permalink.

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