Anal Doesn’t Hurt at All… On The “Cool Girl” and Sexual Expectations

I’ve been rewatching all four seasons of Crazy Ex Girlfriend over the last couple of months.

Fair warning, this post contains spoilers for all four seasons of the show, so if you haven’t seen it yet then you might want to skip this one.

Early in season 1, main character Rebecca attends a yoga class taught by Valencia, her love interest Josh’s long-term girlfriend. Naturally, the class turns into a musical theatre style song-and-dance routine which exists entirely in Rebecca’s mind. In this case, the song is I’m So Good at Yoga, a Bollywood parody in which Valencia boasts about all the ways in which she’s better than Rebecca. (“I kiss my own pussy, can you do that?”)

It’s a pretty funny scene that will speak to anyone who has ever had an overactive imagination about all the ways in which other people are judging them. But since this is a sex blog, I want to talk about this one throwaway line I wasn’t able to get out of my head after my rewatch:

“Anal doesn’t hurt at all /
Most times I prefer it.”

Given this show’s razor-sharp, on-point social commentary on everything from mental illness to dysfunctional workplaces to parenting, there is simply no way that creator Rachel Bloom didn’t know exactly what she was doing with this line. And that’s what I love about it – it’s another example of this show’s ability to pack SO MUCH into just a few words.

For me, this is a statement on the idea of the “cool girl”. Remember that expression, we’ll come back to it in a minute.

Sexuality policing and the male gaze

In this scene, we see the extent to which Rebecca’s insecurities are focused on what people – especially men, and most especially Josh Chan – think of her. One of the main ways in which she conceptualises Valencia as “better” than her is Valencia’s seeming willingness to behave like a male sexual fantasy. (Which makes it all the more pleasing when – big spoiler incoming – Valencia both becomes a much nicer person and comes out as queer, settling down with a girlfriend, in later seasons).

Unfortunately, we live in a world where women are judged on how well they service the heterosexual male gaze. We’re taught to judge ourselves and each other on our looks from early childhood. It’s no accident that 78% of girls dislike their body by the age of 17 (including 40-60% of elementary school girls). (Source.)

As we get older, our sexuality is policed, too. Be available, but don’t be a slut. Service male desires, but don’t have your own. Be simultaneously a virgin and a whore. The expectations put on women and those perceived to be women are immense, contradictory, and devastating from a mental health perspective.

The “cool girl”

If you’re a women or perceived to be a woman, you might have been described as a “cool girl” (or wished to be one) at some point.

So what is the cool girl (CG)?

Simply put, she’s a cis heterosexual male fantasy who doesn’t actually exist. The CG is down for whatever most pleases the men around her. She eats burgers without worrying about her figure (but is still a size four, of course.) She’s “one of the boys”, but still wears high heels and a full face of makeup. She’s “sexually liberated”, but only in so far as it pleases men. Her sexuality is about their desires, not her own.

The thing is, going back to Crazy Ex Girlfriend for a second, is that when we get to know Valencia, it becomes apparent that she is so much more than just a CG. She’s pretty one dimensional and dislikeable in season 1, but we come to realise that that’s more due to Rebecca’s projection than her actual character. (Let’s be real, I’d probably also come across as a mega bitch if my partner’s ex reappeared in town after ten years with the express intention of breaking us up.)

But Rebecca is so insecure that she conteptualises Valencia as the CG – hot as hell, sexually adventurous, every man’s dream. But the viewer, and Rebecca, later get to see that Valencia is actually just as insecure and just as much a victim of the patriarchy. She has desires, needs, and vulnerabilities just like anyone else.

So about “preferring” anal…

For me, this particular line was entirely about Rebecca positioning Valencia as a cool girl who, naturally, would enjoy the same things cishetero men are supposed to enjoy. Naturally, the perfect CG would not only do anal, she’d prefer it.

Anal sex was a particular point of contention in my first sexual relationship. I wouldn’t be exaggerating to say that my boyfriend was pretty obsessed with the idea (bearing in mind I was fifteen years old the first time it was brought up.) Much later, I reluctantly did it because I thought I was supposed to do it. Because the women he watched in porn did it, the women he read about in magazines did it, the other women he’d been sneakily flirting with said they would do it.

Authentic desire vs. mainstream pornification

I’m pro-porn, as long as it’s consensually produced and the performers remain in control and are compensated fairly for their labour. However, I also recognise that the mainstream porn industry has a lot to answer for, and one of those things is the fact that many teenage boys now think that pressuring their girlfriends for anal is normal.

Anal sex should be approached like any other consensual kink. If you’re into it, awesome – have fun. If you’re not, that’s totally cool too! I actually did come to enjoy it after those negative early experiences (much later and with a different partner). But that was only able to happen in a space of safety, care, and zero expectations.

I wish we could think of sex as a vast menu of potential options to choose from, rather than a space where certain acts are accepted. I have a lot of respect for Dan Savage and his work, but every time he says “oral comes as standard” it makes me cringe. There shouldn’t be any standards, beyond informed consent and mutual pleasure!

If we’re into anal sex, we should be able to express that and enjoy it free of shame or stigma. But it should be considered equally fine to say hey, anal actually does hurt and I actually don’t like it. When mainstream, male gazey porn is the first introduction many young people have to sexuality, especially when it’s not accompanied by comprehensive sex education, we end up in a place where young men come to expect a certain kind of “performance” from their sexual partners.

If you absolutely need a certain sex act in your life to be fulfilled, you’re within your rights to (and probably should) seek out partners who are also into that thing. (See: why I won’t date entirely vanilla people. There’s nothing wrong with vanilla sex and I enjoy it sometimes, but I need regular kink in my life to be happy and satisfied). But I really want to do away with the idea that any sex acts – penetration, oral, hand stuff, anal, kink – are expected or standard.

Sexual compatibility matters. But what that means will vary for every couple and every individual. Authentic expression of desire is what we should strive for, not matching some impossible male gaze standard.

Cool Girls don’t actually exist, and I love the way Valencia’s character arc slowly dismantles the idea one piece at a time.

I wasn’t expecting this piece about a throwaway one-liner in a TV show to run over 1300 words, but here we are! If you enjoyed this, you can always buy me a coffee to show your appreciation. Oh, and don’t forget to sign up for my newsletter!