Bo Burnham’s “Inside” is a Fucking Masterpiece

Kate Sloan

Content note: This post contains discussions of depression, anxiety, and suicidal thoughts.

 

I think some of my friends think I’ve lost my mind a little bit. I keep talking about Bo Burnham lately, and I think many of the people in my life are like, “Wait. What? Isn’t that the kid from YouTube who wrote shitty songs making fun of every marginalized group under the sun? You’re into HIM now?”

Well, to be fair, I’ve unironically (though sometimes surreptitiously) loved Bo for over a decade, in part because it’s clear that a lot of his past missteps were just pointed leftist irony that viewers didn’t interpret as such, being (reasonably) hesitant to assume a cis straight white guy has good intentions. (“If you were offended by that, it was ironic,” Bo explains after performing a song called Straight White Male in his special Make Happy. “Isn’t that fun? I meant the whole opposite of it!” The tone is jokey, but like… he’s right. That is what he, and other irony-based crooners, do.) It’s fine if you don’t forgive him; you don’t have to. BUT ALSO, he has come a long way since those YouTube days. Like, a loooooooong way.

Bo’s latest Netflix special, Inside, touched me in a way that no piece of art has in a very long time. Hannah Gadsby’s Nanette came close, as did the movie Ex Machina and the Andy Shauf album The Neon Skyline. All of these works of art accessed deep wells of emotion in me through razor-sharp relatability and big themes. But I really think Inside might be my favorite piece of art I’ve consumed – in any medium – for at least the last five years. I’m not fucking kidding, y’all.

If you haven’t seen it, first of all, SEE IT, and secondly, here’s what it’s about: Bo, like many of us, found himself cooped up inside during the pandemic, socially isolated and inundated with terrible news on the internet every day. But unlike many of us, he had the technical skills and creative vision to sequester himself in a single room with a camera, a lighting setup, and a bunch of audio equipment, and create a 90-minute musical comedy special that somehow expresses a giant range of quarantine emotions and 2020 Big Moods.

Toward the beginning of Inside, Bo’s hair is beginning to get long, a beard is forming on his face, and he seems merely perplexed and thrown by the pandemic, like we all were. As the special progresses, however, his hair grows longer, his beard expands, and his mental health starts to slip. But he keeps making the special anyway. We learn, through his occasional tiny disclosures of big truths, that working on the special has become his tether to the world, the one thing keeping him semi-afloat as his mental health reaches “an ATL (all-time low).” As a creative who has, myself, used writing or music or podcasting to give me a sense of purpose and belonging when I was unable to find one any other way, this resonated so hard that I often found myself yelling “WOW” or “YIKES” or “DRAG ME, BO” at the screen.

Bo’s songwriting has levelled up IMMENSELY since his last special, Make Happy. As a music nerd, that’s one of the main things I noticed on my initial watch of Inside. He was always a highly skilled lyricist and pianist, but his songs until now have mostly stayed within a pretty small range of chord progressions and styles. In this special, he reaches almost Sondheimian levels of intricacy and beauty with his songwriting, and explores styles like hiphop, folk, and cabaret. It feels like his ability to execute a project has finally caught up with his creativity and vision, such that every song in this special functions wonderfully as an actual song, rather than just being a framing device for Bo’s clever jokes and witty observations.

I can’t possibly tell you about all my favorite parts of this special because there are frankly too many. But here are a few:

• An early song, “Healing the World with Comedy,” gets us all on the same page, in Bo’s signature half-joking-but-kinda-serious style. He establishes right off the bat that he knows comedy is simultaneously pretty useless in the face of worldwide strife and also potentially a platform through which he can effect change. As an artist who also sometimes struggles with the question of “Why the fuck am I doing this when so much awful shit is going on?” I found this one screamingly hilarious and also useful as a reminder to use my platform for good. “If you wake up in a house that’s full of smoke, don’t panic – call me and I’ll tell you a joke,” Bo offers; “If you see white men dressed in white cloaks, don’t panic – call me and I’ll tell you a joke.” It’s a chilling reminder that art can only do so much.

• There are two sort of silly-sexy jams in this special, called, respectively, “FaceTime with My Mom” and “Sexting,” which are about… exactly what they sound like they’re about. In a very classic Bo Burnham way, these songs crack you up for most of their duration and then hit you with an unexpected emotional punch – like when Bo’s mom puts his dad on the phone and they have a stilted, emotionally disconnected conversation (#relatable) or like the one frame in “Sexting” where you can read Bo’s paragraph-long textual meditation on the line between playfully begging to see someone’s nudes and pressuring them in a way that feels uncomfortable. Also, these songs are both absolute bops.

• There’s a lot of… gender… in this special?? There is, in fact, an entire song (“White Woman’s Instagram”) where Bo is essentially in drag, albeit with a beard. And, um, my gay ass can confirm that he is pulling it off. I was wondering what other people thought about this, so I typed “Bo Burnham gender” into the Twitter search bar, and there are dozens upon dozens of trans and nonbinary people tweeting that Bo gives them gender envy. Understandable, tbh.

• An extended bit in which Bo does “commentary” on one of his own songs, and then does commentary on his commentary, is a brilliant depiction of the self-criticism and self-policing that can come with depression and anxiety. He does something similar in another section where he takes on the role of a hyper-masc Twitch streamer playing a video game that is actually just Bo’s own life: sit in a room, cry, play piano, go to sleep, start the day over again. Both of these bits crystallize an overarching theme of dissociation, derealization, depersonalization, and the way that the internet encourages us to view ourselves and our lives through an externalized lens.

• One of the prettiest songs in the special laments, “Can one be funny when stuck in a room?” In reflecting on his own past tendencies to self-isolate as a protective mechanism, Bo sings, “Well, well! Look who’s inside again! Went out to look for a reason to hide again,” at which point I felt like someone had stabbed me through the heart because DAMN, @ ME NEXT TIME, BO.

• Speaking of Bo’s (numerous) past fuck-ups, there is a song toward the middle of the special where Bo fully, explicitly, and sensitively apologizes for the problematic jokes he built his fame on. “Are you gonna hold me accountable?” he dares, almost begs. In classic Bo fashion, the song is simultaneously self-reflective and hilarious. It’s filmed as an athletic scene reminiscent of a Rocky training montage, which contributes to the overall image of masochistic self-flagellation and doing penance for past mistakes. I kept screaming at the screen “I CAN’T BELIEVE HE’S DOING THIS” at this point, because it really is that rare to see someone of Bo’s demographic owning up to what they’ve done. “Bitch, I’m trying to listen; shit, I’ve been complacent,” he sings toward the end. “If I wanna catch up, first I gotta ‘fess up.” Too true.

• Bo’s really bummed about turning 30 during the making of the special because he thought he’d be done with the special, and ideally with the pandemic, by then. Again… relatable as fuck. Then he sings a song about turning 30 which is a beautiful meditation on aging, feeling “out of touch,” resenting others who are “adulting” better than you are, and just generally mourning the passage of time. He does his own light show during this song, pressing pedals and rotating a handheld light around his nearly-naked body, orchestrating his own vulnerable self-exposure. (There is also a whole lotta bisexual lighting and genderless hotness in this song, tbh.)

• The catchiest song from the whole special, in my opinion, is a Lizzo-esque hiphop/pop tune that begins thusly: “Wake up at 11:30, feeling like a bag of shit. All my clothes are dirty, so I’m smelling like a bag of shit.” It goes on to paint a perfect picture of not only depression (which many other artists have tackled) but the specific brand of dark, self-effacing humor that can emerge out of a bad depressive spell. It’s not the most thematically complex song, especially compared to some of the others in this special, but it’s the one I find myself singing the most, and laughing at so hard that my depressed body shakes. (I’m listening to it right now as I write this, and dancing in my chair.) There is also just something about seeing a person perform a slick, upbeat song with perfect lighting choreography… while wearing a white T-shirt and baggy shorts. You get me, Bo.

• Probably the objectively best song in the special is “Welcome to the Internet,” an absolutely chilling and devastating takedown of the internet and the ways it corrupts our minds. After I watched this for the first time with my spouse, they observed, “I think that’s the best thing that’s ever been written about the internet,” and I had to agree. That’s high praise, friends.

• A low-key folk song toward the end of the special grapples with existential dread, climate change anxiety, and dissociation in the internet age. It’s the prettiest Bo’s voice has ever sounded, and perhaps the most sensitive and sincere he’s ever been. “There it is again,” he croons sweetly, sadly, “that funny feeling.” He never names exactly what “that funny feeling” is, but by the end of the song, I always feel like, Yep. I know that feeling. I know it well.

 

Overall, I simply cannot recommend this special enough for anyone who struggles with mental health, their relationship to the internet, the weirdness of being a public figure, and/or mounting dread about the state of humanity. It’s a “comedy special,” sure. It’s also a fucking masterpiece that depicts, better than anything I’ve ever seen or heard, what it’s like to be a certain type of human in this terrifying time. It’s given me comfort, solace, and laughs – if just because it showed me that I’m not the only one feeling “that funny feeling.” Not at all.

A Penis Size FAQ

Kate Sloan

 

Does penis size matter?

The short answer: It matters to some people, and less so (or not at all) to others. Whatever your size, the important thing is to find a partner (or partners) who enjoy it. Those people exist, regardless of what size you are, I promise.

Longer answer: Anyone who tells you penis size universally doesn’t matter is lying to you, but anyone who tells you penis size always matters, or that bigger is always better, is lying to you too. The truth is that different people have different preferences. I know you want a simple answer, but there isn’t one, because human sexuality is infinitely vast and variable, and so are human bodies.

There are “size queens” out there, yes. There are people who are shitty and judgmental about penis size out there, yes. However, there are also people who prefer smaller dicks because they find them more comfortable, less painful, easier to accommodate orally or anally, more aesthetically pleasing, or any number of other things. As with literally everything sexuality-related, we’re all different and it’s just a matter of finding the person/people you’re compatible with.

Keep in mind, too, that the vast majority of people with vaginas don’t orgasm from vaginal penetration alone. The clitoris, not the vagina, is the pleasure equivalent of the penis – meaning that pleasure and orgasm without clitoral stimulation are about as rare and as difficult as pleasure and orgasm without any penile stimulation (i.e. certainly not unheard of, but not the default for most people). Penises aren’t generally magic orgasm-producing machines for the people you fuck them with, and that’s true regardless of their size.

 

Does penis size matter to you, personally?

Sure, in that I have a different experience with different penis sizes, in much the same way that a huge dildo feels different from a smaller one. Neither is inherently better than the other. It depends entirely on my mood, where I am in my cycle, any health issues I’m going through at the moment, which erogenous zone(s) I’m hoping to target, what fantasies I’m enjoying recently, and other such variables.

 

What does “average-sized” mean in the context of penis size? / What “counts” as big or small?

Studies generally find that the average penis size is in the neighborhood of 5 to 5.5 inches long. I would personally define a big dick as being 7” long or more, and a small dick as being 3.5” or less, but keep in mind that a) there’s nothing inherently wrong with having a small or large dick, as discussed, b) that doesn’t take girth into account and it can be a pretty huge factor (so to speak), and c) different people will define these terms differently depending on their preferences and amount of experience.

If you’re wondering if your penis is “normal,” 1) it probably is, and 2) a doctor can answer that question for you better than I can if you’re really worried.

 

Can I change my dick size?

There are surgeries for this, but I wouldn’t recommend them. They seem risky and not all that necessary. There are also pills/supplements whose makers claim they can alter your dick size, but I’ve seen zero evidence that this is at all accurate.

In my experience, usually body-related insecurities are more about your preconceptions and perceptions than your actual body (barring certain potential exceptions like gender dysphoria), so if you’re worried your dick isn’t pleasurable enough, you’d be better off upping your oral sex game and getting really good at wielding dildos than getting a dangerous procedure to alter your most sensitive organ based on your limited notion of what partners might find pleasurable.

Penis pumps enlarge the penis temporarily, and are sometimes used regularly over time to encourage penile growth, especially for transmasculine folks’ dicks after going on testosterone. I also know that there are stretching devices that can lengthen your dick when used in the long-term, sort of like braces for your penis. But again, personally, I don’t consider these measures worthwhile when there are so many other ways you can work on your sexual skill and sexual confidence.

Aside from surgery, I don’t know of any way to make your penis smaller.

 

What if my partner doesn’t find my dick size satisfying?

Well, first off, if they’re expressing that to you in a way that feels hurtful and mean, that’s a red flag. Body-shaming of any kind in a relationship is almost always a bad sign about your partner’s attitudes on bodies and their ability to be tactful and polite.

Beyond that, if you want to give your partner the sensation of getting fucked with a larger cock, you can use silicone penis extenders, fuck your partner with a dildo (possibly one that is strapped onto your body with a harness), use your fingers/hand, or use a penis pump immediately prior to sex. Check out the /r/SmallDickProblems subreddit for more advice.

If your dick is too big for your partner, you can try using an Ohnut to limit the amount of length you can fuck them with, use smaller dildos/strap-ons on them, use your fingers, use a hell of a lot more lube, do more “foreplay,” or just do non-penetrative sexual activities. (As noted above, most people with vulvas get off most readily from clitoral stimulation anyway.) The /r/BigDickProblems subreddit also contains lots of advice on this.

Presumably, your partner is attracted to you because of who you are, not just what your dick can do. If that’s not the case, you may not be in a healthy and emotionally safe relationship.

 

What’s more important: length or girth?

Again, depends entirely on the person, and may change from day to day or from moment to moment. There isn’t just one “right answer” to this question, and anyone who tells you otherwise is lying to you, probably to make you feel insecure and/or sell you something.

Length may be important if your partner likes A-spot stimulation or cervix stimulation, for example, while girth may be important if they like intense G-spot or prostate contact. Some people may want a shorter or skinnier dick for comfort reasons, or because those can hit their spots more easily.

Hell, I’m a sex toy reviewer and thus intimately familiar with my own preferences, and even I can’t say definitively whether I care more about length or girth, because it depends on the day, the sensations I’m seeking, any health issues I’m going through, etc. Luckily, sex toys exist, so I don’t have to rely on a partner’s penis to provide any and all penetrative sensations I might be craving at any given time. (Sensing a theme here?)

 

How big does a penis have to be to hit the G-spot or prostate?

Usually about 2-3″ long, ideally with a curve (either upward or downward will work, depending on the position). However, again, sex toys are great for this. In many cases they’re better than dicks at hitting these spots. (I recommend the Pure Wand and Seduction.)

 

How big does a penis have to be to hit the A-spot?

I think a lot of people assume I am a hardcore size queen because I like A-spot stimulation, but… nah. Many partners of mine have been able to reach my A-spot easily with their fingers, including those with shorter/smaller fingers. It’s all about angling and positioning. Have the receptive partner pull their knees closer to their chest to shorten the vagina’s length, and you’ll have an easier time reaching the A-spot with your dick, your fingers, or a toy. Anything upwards of about 5″ can hit my spot just fine, and sex toys exist anyway so it’s not like a penis is the only option here.

 

Will using a dildo that’s larger than my penis make my partner leave me/like my dick less?

Unless your partner is literally only dating you for the usage of your penis, no, it’s unlikely that anything like this will happen. I know that it’s easy in a phallocentric culture to feel like your penis is the only thing tethering you to social and sexual success (whatever the hell that means), but there is more to a relationship – and more to sex – than the size of your cock, I promise.

A dildo cannot pay attention to your partner’s signs and speed up or slow down or fuck harder or softer as needed, the way you can. A dildo cannot whisper filthy shit in your partner’s ear or roleplay their favorite fantasy with them like you can. A dildo cannot hold them close after they come and make them feel safe and loved the way you can. You are so much more than a dildo, and you can do so much more than a dildo can. If you don’t know/believe that, consider working through your self-esteem issues with a therapist – you deserve to recognize your own value as a human being beyond your genitals!

 

What condom is best for my penis size?

Many people don’t know that condom fit can have an enormous impact on how pleasurable and comfortable sex is for you. I would suggest checking out the Find Your Size page on LuckyBloke for an introduction to this.

Keep in mind, when shopping for condoms, that many are labeled in misleading ways (e.g. Trojan Magnum condoms are the same size as some other brands’ standard/medium size), so looking at the measurements will give you a better idea of potential fit than the product’s branding will.

If you want a super custom fit, One makes a condom line called MyONE that seems to be the best option for people who chronically struggle with condom sizing. My partner got to try some in their size recently and really liked them; they said it felt like wearing a perfectly tailored suit.

 

If you’re accustomed to a particular penis size, is it normal to have trouble adjusting to/enjoying a different-sized one?

Sure, especially if you have very particular preferences (which isn’t morally wrong or anything, and is nothing to be ashamed of, as long as you’re not shitty about it).

Sex toys are your friends. They can help you access sensations you’re not otherwise able to access, including the sensations of being penetrated by something smaller or larger than your current partner’s penis. Don’t frame this as a shaming thing if/when you bring it up; you don’t want to give your partner a traumatic complex about their dick. Size is just one variable of sexual sensation, and there doesn’t have to be a value judgment attached to the idea of wanting to be fucked by something smaller or larger.

As mentioned above, silicone dick extenders and strap-ons can help if you really want to feel like your partner is fucking you with a dick that’s a different size from their own.

 

Does ball size matter?

To some people, yeah. Everything you can think of matters to someone. I have never really cared about this or even noticed variances in ball size all that much, personally, though.

 

Will dick size affect my experience with a stroker?

Potentially, yes. While many of these toys are at least partially flexible/squishy, some have less give than others. If you’re on the larger side, I’d suggest searching the names of any potential purchases in the /r/BigDickProblems subreddit to see if anyone there has reviewed that toy for their particular dimensions. If you’re on the smaller side, I’d recommend toys by Tenga, which tend to be snugger-fitting than, say, Fleshlights. It’s always a good idea to read sex toy review blogs, too; some reviewers mention their dick size, so you can more easily compare their anatomy to your own and find out whether the toy they liked would work for you too.

 

Do big dicks stretch out vaginas/anuses?

Temporarily? Yes. Permanently? No. These orifices are made of tissue that can expand as needed to accommodate various sizes of penetrating objects, but reverts to its original position/size in due time afterward. Anything you’ve ever heard about loose, stretched-out pussies or butts is a medically misinformed myth, usually propagated with the intention of discrediting and dehumanizing anyone perceived as being a “slut.” I know you don’t want to participate in a practice as vile and demeaning as systemic slut-shaming, so I know you’re not going to perpetuate this myth anymore. Right?

 

How does transitioning affect penis size for trans and non-binary people?

I’m cis and don’t have firsthand experience with this, but would recommend anything written by Ana Valens on the subject (for transfeminine people). As for transmasculine folks, here’s an episode of the Dildorks where I talked with Bex about his T-dick growth (among other things), and this article by Oak is also great.

 

Is there any equivalent insecurity to penis size that people with vaginas have?

You know, every time I’ve been asked this, I’ve immediately thought that for cis women (the only gender group I’ve been a part of, and thus the only gendered experience I can directly speak to), our entire bodies are scrutinized and criticized in similar ways to how penis size is discussed for cis men. Our overall body size, boob size, vaginal tightness, vaginal scent and taste, and capacity for vaginal lubrication are some more specific areas where we’re encouraged to be desperately insecure and self-hating. I don’t think these things are directly comparable because they manifest somewhat differently, but, short answer: yes. People with penises don’t have a monopoly on feeling shockingly profound shame and self-doubt about the sexual attractiveness and viability of their bodies. That widespread shame sucks, and it needs to change – for everyone, of every gender and body type.

 

What questions do you hear a lot about penis size?

Behind the Seams: Vaccine Queen

Kate Sloan

May 16, 2021

A while ago, I read an article about people getting dressed up for their vaccinations. This idea immediately resonated with me: I love dressing up for things and find that it helps imbue events with extra significance for me. The ritual of assembling my femme ensemble helps me feel more put-together, centered, and prepared.

Shortly after reading that article, I wrote a poem about why it would feel emotionally impactful to wear something cute to a vax appointment. I won’t share it here because I’m waiting to hear back about potential publication, but one of the things I wrote in the poem was that I wanted to wear a leopard-print dress to show I was still wild after a year+ of captivity. On the day of my actual first dose, I hovered in front of my closet, trying to decide which dress would be best, and then I remembered that poem as my eyes alit on this leopard-print dress. Of course! It was the natural choice.

I got a lot of compliments on my look as I waited in line outside the clinic. I hadn’t realized, until people started commenting on it, that I’d inadvertently adorned myself with multiple rainbow hearts. The nurse who gave me my shot complimented my pen and pencil tattoo. Overall, a wonderful day.

 

What I’m wearing:

• Leopard-print skater dress – American Apparel, via eBay
• Black KN95 mask layered under a Pride heart mask from Threadless
• Red sparkly heart necklace – Tarina Tarantino
• Rainbow heart prescription sunglasses – Zenni
• Pink leather Cashin Carry tote – Coach (a findom gift from my love)
• Black leather harness boots – Frye

May 27, 2021

My psychiatrist told me recently (as he’s told me many times before) that I should try to go on more walks. “I always tell my patients to do that,” he said, “but recently I took some time off and started going on daily walks myself, and wow, it really makes a difference!” Unfortunately for my lazy ass, he’s right.

My dominant asked me what they could do to incentivize me to take more walks, and after pondering it a bit, I replied that I thought they should put “take a walk” on my to-do list on days when my workload seemed lighter, and provide a small assignment to do on the walk, something specific to photograph. I felt that would give me motivation, momentum, a goal.

It’s been working out well so far. I wore this outfit on a nice springtime walk with the intention of photographing a statue, for example.

 

What I’m wearing:

• Pink ribbed tank top – the Gap
• High-waisted skinny jeans – Madewell
• Pink cowboy boots – Jeffrey Campbell
• Pink leather Cashin Carry tote – Coach
• Turquoise Toy Story-print mask – an Etsy shop
• Hair in pigtails because it’s long enough to do that now!

May 31, 2021

This was my last day at my social media dayjob (which I call a dayjob purely out of habit; at the point that I decided to leave, it was only taking up 3-5 hours a week and bringing in ~7% of my income). In the pandemic age, I find it’s extra difficult to celebrate successes. You can’t invite your friends to go for a pint and clink your glasses together over what you’ve achieved, or take a mini-vacation as a reward for a job well done. So I asked my partner what they thought I should do to commemorate entering the land of the fully self-employed, and they suggested I order a bottled cocktail from Civil Liberties, my favorite bar.

I went online and ordered a double serving of the Call Me Maybe, a yummy drink involving grapefruit juice, fennel, fino sherry, and tequila. Then I decided to walk all the way to the bar – about 45 minutes – because it was a beautiful day. I think this was the first time I’d worn a crop top outdoors in nearly a year. Yay, spring!

 

What I’m wearing:

• Royal blue crop top – Forever 21, I think?
• Black A-line jersey skirt – ASOS
• Black bike shorts (worn underneath to help with chub rub) – American Apparel
• Red socks – the Gap
• Nike Air Zoom Pegasus 37 sneakers in teal – a findom gift from my love
• Pink leather Cashin Carry tote – Coach
• Black KN95 mask

June 2, 2021

Feeling in touch with my femmeness has been challenging this past year. I think that as much as my inner angry feminist often wants to snarl “I don’t dress up FOR YOU!!” there is nonetheless an element of my aesthetic that doesn’t feel worth performing if there’s no audience for it. Gender and style are both concepts that have an inward component as well as an outward component, and that outward one is hard to reckon with during a pandemic.

I put on this sweet floral dress to go buy some limes and mint so I could make a fave summer cocktail, the Southside, when having drinks with my friend/roommate Sarah later that night. We may not have been able to go sit on a pub patio or hang out at a cocktail bar, but I was determined to make our indoor lives feel summery and celebratory nonetheless, dammit.

 

What I’m wearing:

• Black/white/pink floral dress – CowCow
• Black leather Frye harness boots
• Pink leather Cashin Carry tote – Coach
• Black KN95 mask

June 3, 2021

Comfiest “outfit” ever. Sometimes I attempt to make my loungewear ensembles look aesthetically pleasing and intentional (as opposed to the times when I just throw on an oversized T-shirt from some rock concert of yore, pair it with underwear and fuzzy slippers, and call it a day).

I had recently reorganized my T-shirt drawer and resultingly rediscovered a bunch of shirts I forgot I owned, like this black cropped tank top, which is an essential item for when I want to feel summery but also goth.

 

What I’m wearing:

• Black ribbed cropped tank top – Forever 21? H&M? Not sure
• Black modal lounge pants – the Gap
• Tie-dye Bombas ankle socks – a gift from Matt’s mom

Menstrual Cup Tips & Tricks

Kate Sloan

I’ve been using menstrual cups for more than 12 years. When I was 16, my best friend at the time bought one from a local health food store because she was concerned about the environmental impact of pads and tampons (reasonably so) and wanted to try a more eco-friendly alternative.

I, on the other hand, had been using menstrual sea sponges (which I hadn’t yet learned are probably not safe to use), but had found that they couldn’t contain my flow and would leak whenever I sneezed (!!), so I wrote an email to my friend. “I’m looking at the DivaCup,” I said. “What are your experiences? Do you love it? Have you had any issues with it? Any words of warning?”

My friend wrote me back a glowing review in which she said she loved her DivaCup the way she loved her Coach bag, because both were built to last a long time. “It feels a lot sexier than tampons, too,” she wrote, “because it’s so much cleaner and because of that no-leakage factor.” I was sold, and bought my first menstrual cup online a few days later.

In the years since, I’ve tried many different cups, and have learned a lot about the best ways to use them. Here’s some of what I learned the hard way, presented here so that you can learn it the easy way!

 

Cup Selection

• There’s a great LiveJournal page where the ever-resourceful menstrual cup community has assembled sizing info on many of the cups currently available, as well as their capacity and some other useful stuff. If you’ve tried a cup before and didn’t like the sizing for your particular anatomy, I would suggest going on there and looking for a cup that’s longer/shorter/wider/thinner (whichever you think you need).

• While different-sized cups are often described as being suitable for people who have or haven’t given birth vaginally, that’s definitely not the only factor that can decide which cup size and shape is most comfortable for you. Take companies’ recommendations into consideration, but know that you know your own body better than they do.

• I’ve probably tried 8-10 different kinds of menstrual cup over the years, and my all-time favorite is the large Yuuki cup in firm silicone (they also make a softer silicone version, and a smaller size). I’ve noticed that with my particular anatomy, soft silicone cups tend to leak more, especially if I’m moving around a lot. I find, by contrast, that the firm Yuuki pops open easily when I insert it and almost never leaks when inserted properly (see below for insertion tips).

• A while ago, I was sent the Intimina Ziggy menstrual cup, which has a different shape and insertion method than most cups. I find that its flatter shape is sometimes more comfortable for me on days when my period is causing some vaginal discomfort/sensitivity. It also takes less hand dexterity to insert (you just pinch it, push it in, and tuck the front rim behind your pubic bone), so I often choose it instead of my Yuuki when my hand pain is flaring up. The Ziggy definitely leaks more than my Yuuki, but if I’m just lying around at home as I’ve mostly been doing lately, that’s not a huge deal for me.

 

Inserting a Cup

• First of all, if your cup has a stem to make removal easier, be aware that cutting the stem off (carefully, with sharp scissors) is always an option. I cut the stem off my Yuuki after only a couple of wears because I found that it was poking me in the vaginal wall and wasn’t necessary for removal. Some people just trim the stem a bit shorter, depending on their body and preferences.

• I have found that running some cold water over a menstrual cup right before insertion causes the silicone to temporarily firm up a little, which makes it easier to insert the cup.

• Your cup probably comes with insertion instructions, so look at those. There are numerous different ways to fold a cup so it can be inserted; I usually sort of fold mine in half so it resembles a “C” shape from the top, and slide it in while it’s folded.

• Lube can be helpful for insertion, especially when you’re first learning how to do it. Just make sure to only use water-based lube because other kinds may damage the cup or mess with the balance of your vaginal flora.

• Once the cup is inside you and past your pubic bone, you need to get it to unfold/open up. I usually do this by putting my thumb on one side of the cup and my index finger on the other side, and gently rotating/twisting the cup until I feel it open up. Sometimes doing Kegels can also help with this.

• Rotating the cup, as described above, can also help create a mild “seal” between the cup and your cervix, thereby reducing leakage. I find that only some cups are consistently able to achieve a good seal in this way, my beloved Yuuki being one of them.

• I know that this process sounds complicated, but I promise that once you’ve done it a few times, it gets much easier and more intuitive. I barely have to think about putting mine in nowadays; it comes very naturally.

 

Wearing a Cup

• Barring vaginismus or other legit vaginal health issues, you shouldn’t generally be able to feel a cup while you’re wearing it (in much the same way as a tampon), or at least it shouldn’t be uncomfortable at all. If it is uncomfortable, you may not be inserting it deeply enough or you may be using a cup of a size or firmness that doesn’t work well for your anatomy.

• It’s probably a good idea to wear a pantyliner or pad for at least the first few times you wear a cup, incase of leakage. But even after wearing cups for 12+ years, I’ll still sometimes put a reusable pad in my underwear on really heavy flow days/nights, just incase.

 

Removing a Cup

• You should not wear a cup for longer than about 8 hours at a time without, at the very least, taking it out and rinsing it off before re-inserting it. This is because menstrual cups obstruct the vagina’s self-cleaning process, so it’s easy for your vag’s natural balance of flora to get thrown off if you wear a cup for 10-12+ hours without rinsing it. Trust me, I’ve gotten bacterial vaginosis from doing this before; learn from my mistakes!

• The first step when removing your menstrual cup is to break the seal between the cup and your cervix. In my experience, the best/easiest/fastest way to do this is to press a finger firmly against the side of the cup, just below the rim; this causes the cup to bend inwards, breaking the seal. It is especially important to MAKE SURE you break the seal before removal if you have an IUD in; some doctors say you straight-up can’t use menstrual cups if you have an IUD, because of the risk of the cup “sucking” the IUD out during removal, but if you break the seal properly every time, there will be much less risk of that. (I’m not a doctor, though, so ask yours if you’re not sure!)

• Once the seal is broken, you can gently pull the cup out. I usually do this over the toilet so the blood goes in there, but beginners may want to do it in a shower/bathtub at first in case of splashing or spilling. Like insertion, removal gets much easier with repetition.

• When you remove your cup to empty it (which, as I mentioned, you should do at least once every 8 hours), it’s best to wash it off in the sink before re-inserting it, either with just water or with water and a mild soap. However, if you’re doing this in a public bathroom and can’t get to the sink, you could either rinse the cup over the toilet with some water from a bottle you bring with you, or just wipe it off as best you can with toilet paper before re-inserting.

• Most cups have tiny holes around the rim that help with breaking the seal. Take care to wash these really well whenever you wash your cup, as they can be a breeding ground for bacteria otherwise. I usually fill the cup with soapy water, put my hand flat over the top of it, and squeeze, so that water is forced out of the tiny holes. I’ll do that a few times until I see that the holes have been completely cleared, and then rinse.

 

Cups & Sex

• Some cup manufacturers, like Intimina of the aforementioned Ziggy, claim that their cup can be worn during sex (by which they mean penetrative vaginal sex, which isn’t the only kind of sex, obviously). Personally I have never found a cup that can actually be worn during penetrative sex without leaking a ton, feeling uncomfortable for one or both partners, and/or straight-up obstructing the entire orifice.

• That said, it’s very possible to receive oral sex while wearing a cup (and it may in fact be one of the least messy ways to do so on your period) as well as other forms of external penetration. I’ve also found, in various lazy menstrual masturbation sessions, that some cups sit high enough to give you a little bit of G-spot access for stimulation with fingers or a slim toy (depending on where your spot is located and the size of your cup).

• For the most part, when I want to have penetrative sex of any kind while on my period, I’ll take my cup out at the beginning of the session (and lay down a towel). This is because the sexual arousal process causes the vagina to lengthen and the cervix to lift, so it can be really difficult to remove a cup once you’re already super turned on because you will have to reach farther. Taking it out before any/much foreplay is much easier for me.

• If I’m having sex with someone who I’ve never discussed menstrual cups with, I’ll make sure to give them a brief explainer at some point before sex. It can be alarming to go to finger someone and feel something inside their vagina that you can’t identify and have never felt before!

 

Cup Maintenance

• Cups will usually become discolored over time. This is normal. You can slow down this process by only washing yours in cold water, because warm/hot water encourages bloodstains. I have also found that leaving my cup in the sunshine for several hours (like, say, on a windowsill) helps remove some of the coloration. Some people also like to soak theirs in a 3% hydrogen peroxide solution for a few hours (make sure to wash off your cup very well with soap and water afterward!).

• At least once per menstrual cycle (generally after your period is over), you should sanitize your cup thoroughly. Some people do this using just soap and water; some people go further than that, boiling their cup in a pot on the stovetop or soaking it in various diluted alcohol or bleach solutions. I personally have never had an issue that would cause me to believe that a thorough soap-and-water wash isn’t enough. (This advice only applies if your cup is made of silicone, however. Some are made of more porous materials, such as thermoplastic elastomer; I would not recommend these, but if you do happen to have one, you should clean it more often and more thoroughly than you would silicone.)

• I have had my favorite cup for 10 years and it still looks fine and works great. Silicone cups are meant to last a long time, which is one of the reasons they’re so beneficial ecologically and economically. You can replace yours if/when you want to, but as long as it’s not structurally damaged in some way, you probably don’t have to.

 

Have you tried menstrual cups? What are your fave tips and tricks for using them?

Monthly Faves: Tidy Desks & Morose Masterworks

Kate Sloan

I had quite a dramatic and exhausting month, but a lot of wonderful stuff happened too! Here are some of my fave things from May.

 

Media

• Easily the best thing I watched this month was Bo Burnham’s new Netflix special Inside, which he wrote, performed, shot, and edited himself in his apartment over more than a year during the pandemic. It’s a biting and often hilarious meditation on pandemic life, the internet, depression, anxiety, and the complicated relationship performers have with their audiences. Bo has always been a delightful songwriter but this special contains the best, snappiest, darkest, and most sophisticated songwriting he’s done his whole career. Just watch it!

• Lately I can’t stop looping queer nonbinary singer/songwriter Ben Hopkins’ album I Held My Breath For a Really Long Time Once. Thematically it’s actually very similar to the Bo Burnham special: it’s about depression, loneliness, compulsive behavior (incl. alcoholism), and desiring attention while simultaneously being terrified of it. The magic trick of this album is that all these sad themes are explored through mostly upbeat, danceable, and sing-along-able guitar-forward music. Some of the lyrics about depression and anxiety are just too damn relatable for me, like these gems: “I don’t know how a normal person relaxes/ How to brush my teeth or how to pay my taxes.” “I don’t know how to pay for therapy/ I imagine if I did, I’d have some clarity.” “What’s the point of tidying when everything’s a mess?”

• Matt and I watched the documentary California Typewriter and I found it so affecting and inspiring that I had to snap up a vintage typewriter of my own almost immediately! This film features a whole bunch of famous people who use and love typewriters, but it was John Mayer’s endorsement of them that caught my attention most: he talked about the ways in which the typewriter’s analog nature can unlock hidden modes of creativity, and I have indeed found that to be true so far.

• I’ve played Pokémon games since I was about 8 years old and definitely know more than the average gamer about Pokémon, but watching Twitch gamer SmallAnt’s streams has taught me so much about strategy nonetheless. The video wherein he beats a whole game without dealing any direct damage is incredibly impressive and made for a great late-night intoxicated watch!

• If you enjoy casual sex, or would like to, Allison Moon’s new-ish book Getting It is a must-read. It’s an informative, compassionate, and non-judgmental guide to all things hookup-related.

 

Products

• I’m gonna write about this in detail soon, but I’m loving all the things I’ve bought recently to upgrade my desk setup (a monitor, monitor riser, new SAD lamp, keyboard, mouse, and set of wooden drawers). It is really astonishing how much a “tiny life-improvement project” can brighten your outlook.

• I also upgraded the top of my dresser where I keep all my makeup, skincare products, perfumes, and hair accessories. I bought a rotating storage rack for skincare and makeup brushes, some stackable acrylic drawers and organizers for my makeup and false lashes, and an LED-lit makeup mirror so I no longer have to squint at myself in the half-darkness while putting my face on. Hooray, femme organization!

• I’m going hard on scalp care lately and really loving the Aromatica rosemary scalp scrub and La’dor tea tree scalp clinic hair pack. Seems like a lot of folks have been having scalp issues during the pandemic, possibly due to some combination of stress and less frequent showers (hey, no judgment); maybe these products would help you too!

 

Work & Appearances

• I recently announced the book I’ve been writing for the past couple months: a petite and informative tome for Laurence King Publishing called 200 Words to Help You Talk About Gender & Sexuality. Exciting! (You can still preorder my first book, 101 Kinky Things Even You Can Do – its launch date is a little over 4 months away now!)

• The lovely musical theatre nerds from the Dear Friends podcast invited my friend Brent and I to come answer some advice questions about sex, drugs, and BDSM with them. It was a fun time!

• I was interviewed for Uses This about my work setup. Check it out if you’re curious what hardware and software I use for all my various projects, including this blog!

• In my newsletter this month, I wrote about cuckolding porn, the definition of gender, why typewriters are sexy, and why simultaneous orgasms are overrated.

• For the Andrew Blake blog, I wrote about the usefulness of sex books, vibrators for people with penises, and how to connect with your partner sexually at the end of a long, tiring day.

• On the Dildorks this month, we discussed masochism, public sex, and our current feelings on casual sex.

• On Question Box this month, we chatted with sex educator Dr. Timaree Schmit and burlesque emcee Adam Teterus, actor and storyteller Grace Aki, voice actor Katy Johnson and personal trainer Jordan “Jaxblade” Downs, and kink podcast cohosts Lexi and Gwen. Wow, that’s a lot of awesome people!

 

Good Causes

• In light of the horrendous news about previously unreported deaths of Indigenous students at Canadian residential schools, please consider donating to the Indian Residential School Survivors Society. The cultural genocide perpetrated against Indigenous people by the Canadian government is unacceptable and it’s time for a reckoning (and, ideally, reparations).

• The M’akola Housing Society helps provide affordable housing to Indigenous people in British Columbia.

• The Black Sex Worker Collective provides education, legal help, and healthcare + housing referrals to Black sex workers. They’re also running a conference soon that looks super interesting.