Today’s newsletter could never be anything but a tribute to Anthony Stewart Head, everybody’s Librarian-Bae, Rupert Giles. The original slutty little glasses wearer, the most appropriate male mentor figure ever found on TV, and an actor with tremendous range. RIP…he was far far too young, and this one really hurts. 😿

One of Buffy the Vampire Slayer’s unsung qualities: The Giles and Buffy relationship

The world learned of actor Anthony Stewart Head’s untimely passing yesterday, and in my Buffy bubble, the world mourned Rupert Giles, the mentor and father figure we all wanted (and on rewatches later in life, a Sexy Librarian of the male variety). Of course he was known for other things than Buffy, from the Nescafe ads that made coffee as sexy as it’s ever been to a stint as Frank N Furter in Rocky Horror Picture Show to playing what must be Rupert Giles’s shadow self, villainous ex-husband Rupert Mannion on Ted Lasso. I even own one of his albums, Music for Elevators (which I’m listening to as I write this).

His unexpected loss means that of course it’s time for me to tackle one of the topics I’ve had on my list for this newsletter since I dreamed it up. The topic of the relationship between Buffy and Giles, and why it modeled one of the most healthy adult-youth, mentor-mentee relationships in media in its day. (And probably still.)

The tropes are endless…enemies-to-lovers, disdain/hostility-masking- attraction, violence/anger-becomes-passion, impossibly-young-and-desirable-woman-falls-for-older-man-because-of-his-amazing-intellect, predatory-teen-girl-targets-hapless-man, will-they-or-won’t-they? (that never seems to ask, should-they?).

There was never the slightest hint of any of these tropes brewing between Buffy and her Watcher (a creepy term all on its own), Rupert Giles the librarian.

The show spanned 7 years, taking Buffy from 16 to 22, and if Giles was about ASH’s actual age, he went from 43-49. Buffy, in fact, did have relationships that feel inappropriate now, twice with vampires who were literally a century or two older, and with one of those vampires, the violence-to-sexual-passion pipeline was pretty direct.

And yet, you will never get a creepy vibe wondering if Giles is secretly lusting after his charge. Nor does Buffy ever seem to have a crush on Giles, or flirt with him, or seek his attention in even an implicitly sexual way.

And it’s not that Giles doesn’t have sexuality…in fact there’s a mini-will-they-or-won’t-they between him and computer science teacher Jenny Calendar starting right in Season 1, with an adorable relationship ensuing.

It helps to think about the media of the time to see how unusual the Buffy-Giles relationship is:

  • Moonlighting, from the 80s, is one of my favorite examples of will-they-or-won’t-they gone terribly wrong. We spent years being told the banter (often quite caustic) between Dave and Maddie was barely suppressed sexual tension, and once they finally did give into this passion? It was violent. It came out of fight, and the sex itself was rough. (Not too dissimilar from Buffy and Spike in later seasons’ Buffy.) The difference was that in the 80s this was depicted as passionate, while in Buffy the same kind of energy was depicted as a symptom of Buffy’s feelings of depression and self-destructiveness.

  • Take your pick from many Woody Allen movies post-Annie Hall. Manhattan is the most egregious, but that’s far from the only movie he wrote to show young beautiful women carried away by the size of his (or his avatar’s) intellect.

  • In movies like The Crush (1993), Alicia Silverstone’s obsessive teenager was the villain of the piece. So it’s not just women whose biological clocks are ticking, like Glenn Close’s Alex in 1987’s Fatal Attraction, that are a danger to men, it’s teenage girls too.

There are numerous other examples of all of the above tropes, some even living in Buffy’s relationships with other men in the Buffyverse.

One of the most interesting things to consider years later, after discovering that creator Joss Whedon was beyond problematic with solely his young female stars, is how that Giles-Buffy dynamic was written, acted, and sustained.

Buffy is positioned as a strong woman, but on the weekly she was traumatized and re-traumatized. Big spoilers ahead: In seven years she died twice, was pulled out of heaven against her will, was sexually assaulted by a partner, was loved and left, was injured and re-injured, lost loved ones, had her mind and body manipulated. As a strong woman, she certainly was made to pay. Over and over. And expected to prevail even so.

But the mutual respect and appropriate level of tenderness and care between Giles and Buffy was demonstrated, implicitly, in actions, and stated, explicitly, in words. I assume much of the credit goes to the performances…to the purity of their sub-textual choices…not just the writing.

Giles: "If it's guilt you're looking for, Buffy, I'm not your man. All you will get from me is, is my support... and my respect."

-Innocence, Season 2, Episode 14

It’s one of the very best aspects of the show. It’s why Anthony Stewart Head’s loss hits hard. And it is a credit not just to the writers, but to the actors who were able to play that kind of relationship without any inappropriate subtext and without requiring de-sexualization to do so.

There may not be a business lesson here, specifically, but by showing us what a healthy mentor-mentee relationship looks like, the lesson can be that if you’re getting something other than that Buffy/Giles vibe from someone you’re in a similar kind of relationship with, respect your gut. There is another way, and we all are allowed to build our chosen family and our support system using the Buffy-Giles way as one of our criteria.

I have often said women spend way too much brain power figuring out how to deflect and sidestep and manage unwanted and unhealthy gender dynamics in the workplace…imagine what we could accomplish if we didn’t have to do that? Maybe, like Buffy, we could save the world…a lot.

I’m curious if you’ve clocked these and other reductive tropes in the media you consume. Which one most pushes your buttons?

Travers: "Your affection for your charge makes you incapable of clear and impartial judgment. You have a father’s love for the child, and that makes you useless to the cause.

-Helpless, Season 3, Episode 12

Signposting and sharing

  1. 📺 Next week’s recapping will cover Buffy Season 2, episodes 13 and 14. These are the catalyzing episodes for the rest of Season' 2’s events, and the identity of the “Big Bad” gets swapped in an unexpected and entirely unwelcome way. The second half of Season 2 is definitely considered amongst the strongest series of episodes ever on television in general, not just of Buffy!

  2. 🛠️ Tool of the week/Alt-text generator: While on a WonderTools webinar this week, Jeremy Caplan talked about making his own alt-text generator for the images he posts online. I know alt-text is an important accessibility tool for people with vision impairment, but I confess I’m not always great at including it every single time. But his webinar inspired me to see if I could build my own using Claude. It took a bit of back and forth and trial and error, but I did it and had the satisfaction of using it for today’s newsletter. I have said before and will say again: WonderTools is the absolute BEST bang for the buck I spend when it comes to Substack (or any other) newsletters. You will not regret subscribing if you at all like to nerd out on creation, productivity, AI, or other digital tools.

  3. 📚 This week’s book is wild: I am about an hour from finishing the audiobook of I Am Not a Robot by former WSJ tech reporter Joanna Stern. Joanna served on BlogHer’s 2015 advisory board, so I’ve met her, but it was a long time ago. Still, when I saw this book I wasn’t motivated to get it because I’ve met her, but because the premise is fascinating. Joanna spent the entire year of 2025 using AI to do everything, and she does mean everything. She tried all the tools, the robots, the bots, the hardware and software. She had chatbot sex and a chatbot therapist. She wore every conceivable wearable. She had AI write every email and text. She had AI plan her meals, her wardrobe, and her travel. Some experiments didn’t last (having AI send email and texts unchecked was not at all a good idea, as one example). The book feels like both a discomforting look at the future and an instruction manual on where to draw some lines. Recommend (I borrowed on the library app Libby, which seems germane to mention, particularly this week)!

  4. 🙋🏻‍♀️ Question of the Week: I’m curious if you have any college graduates in your life this graduation season? How are they feeling about the future? We’re hearing a lot about anxiety and dread and booing at graduation ceremonies. It’s pretty depressing. Do you have any college grads who are super stoked going into their next phase of life? (I deeply hope so.)

Bonus: here’s what my alt-text generator looks like. Let me know if you’d like the prompt I used to create it.

My daily tarot card:

Today I drew the Knight of Stakes. (Stakes=Wands in a typical tarot deck.) Wands are the suit of creativity and passions, and it’s two weeks in a row that I’ve drawn from that suit on newsletter day. The Knight of Stakes speaks to bravery and exploration, with a bit of a recommendation to do some planning for it. Like, be brave, but that doesn’t mean you have to be reckless. This certainly speaks to how Buffy and Giles team up…she with the super strength, he with the research and wisdom. But sometimes she has to strategize, and sometimes he has to take up a weapon. I’m reminded that when considering a current challenge the choices aren’t just leave things the same or burn them all down…with more consideration and a little planning, perhaps the bravest thing is something in between? I don’t know yet, but I’ll keep you posted 🙂
A card pull or full reading can help make a specific decision. Or can set the tone for your week. Either way, options are here, my Buffy deck and I are at your service! https://calendly.com/elisacp

Out in the world this week:

Eric Tash and I had a great conversation on his Worthy for Thirty podcast last week. It covers a lot of ground, especially around BlogHer’s origins and scaling. But I also give a bunch of counterintuitive advice, like:

  • Why there’s not much I think I would do differently if “I knew then what I know now”

  • Why raising VC isn’t an actual proof point or even something that will benefit most founders

  • Why I think you should indeed be thinking about your exit from the beginning

  • How your boundaries are part of your “whole self”

Mostly, I’m out here making the case that sometimes it’s good to have someone advising you who neither works for you (like your staff), nor has control over you (like your board). Like I say on my new LI profile (did you check it out yet? I’d love any feedback, especially from those of you who know and have worked with me!), someone who’s in your corner, in your ear, in your business.

So, what Buffy episodes did I watch these past two weeks week?

I watched Season 2, episodes 11 (Ted recap) and 12 (Bad Egg recap)…which aired on December 8, 1997 and January 12, 1998 respectively.

The core #BuffyLifeLesson in Season 2 Episode 11 is something that should be pretty obvious: If you love something let it go. If it doesn't come back to you, don't make yourself a robot and hold women captive 🤷🏻‍♀️ Seriously, there are multiple episodes throughout the series when characters lose someone and go to extreme lengths to try to bring them back. It never goes well. I think more than a series of cautionary tales about grieving loved ones who pass, this is is a series of cautionary tales acknowledging the reality that a woman is at most risk of fatal domestic violence when she is in the process of leaving or has just left.

The core #BuffyLifeLesson in Season 2 Episode 12 is teen pregnancy bad. OK, it might not be that simple, but this is a pretty lightweight episode that takes reminds us that no matter how often Buffy and Gang are out there saving lives, they’re still teenagers and going through the typical teenage stuff, like the tension between hormones and fear of adult responsibilities.

I’m here every week, using pop culture (and Buffy the Vampire Slayer right now) as a jumping off point for everything I’m thinking about professional leadership, personal development, political philosophy, and pop culture. I would love you to join me by subscribing. And I would love you to share the link with other nerds like us!

LAST WEEK’S FINAL WORDS HIT DIFFERENT TODAY #RIPASH

Giles: "Yes, it's terribly simple. The good guys are always stalwart and true, the bad guys are easily distinguished by their evil deeds, and they always lose. And we always win. And nobody ever dies... and everybody lives happily ever after."

Buffy: "Liar."

Giles: "...Yes."

-From Lie to Me, Season 2, Episode 7

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